travel itinerary for portland oregon

The Perfect 3 Days in Portland Itinerary (2024 Update)

Last Updated: February 4, 2024

If you’re planning to have a fun-filled 3 days in Portland and don’t know where to start, then this epic Portland itinerary will have you making the most of your time in Oregon!

So you’re thinking about exploring all of the incredible places to see in Portland, Oregon that millions of its residents have come to enjoy about their city?

Well you’ve come to the right place!

Boasting a diverse culture, spectacular landscapes and enough microbreweries to keep you sampling beer for weeks, Portland is a great place to visit as you tour the Pacific Northwest.

Filled with more activities, attractions and highlights than should be fair for any one city (seriously, check out our full-on guide to the best things to do in Portland ), it’s little wonder it’s quickly becoming everyone’s favorite town in the US.

While a coin toss almost named the city after Boston instead of its namesake in Maine, the west coast city of Portland has had no problem establishing an identity for itself.

Today the city is known for being at the center of the progressive movement that aims to be more environmentally conscious and focused on improving the overall quality of life for its residents.

There’s little wonder that it’s rising through the ranks as one of the top spots to come for a weekend anywhere in the United States.

If you’ve set aside 3 days in Portland, you will have the chance to see Mt. Hood standing tall in the backdrop of the city while you wander the historic Old Town.

You can relax in the many parks and gardens in the city and even saunter off to explore local wines, waterfalls and wonderful food delivered from farm to table.

If that sounds like a good way to enjoy your well-earned vacation, then my post will help guide you with exactly what to do on with your short Portland itinerary.

Ready to get started?

Table of Contents

Portland Saturday Market

Shanghai tunnels, lan su chinese garden & museum, voodoo doughnuts, powell’s city of books, deschutes brewery, multnomah falls, willamette valley wine, hike forest park, an evening back in portland, oregon historical society and portland art museum, pioneer courthouse square, portland japanese garden, international rose test garden, hoyt arboretum, pittock mansion, witches castle, when to visit portland, getting around portland oregon, budget accommodation – hi portland northwest, mid-range accommodation – hotel deluxe, luxury accommodation – the society hotel, budget – voodoo doughnuts, mid-range – q restaurant and bar, high-end – jake’s famous crawfish, how to spend a perfect 3 days in portland itinerary.

A couple of nights here is just scratching the surface of all there is to see and do in the city.

For this Portland itinerary we’ve divided up your time into 3 sections.

We advise you to think about your time in Portland along with the following segments, which you can choose to extend or skip depending on your interests.

The first day will take you downtown into the heart of the city and it’s famous Old Town.

Next, you’ll have a day to get out of town a little for some perspective on why Portland is such a unique place.

Whether you want to hike or simply drive through the scenic country, you’ll appreciate the city of Portland more after this quick excursion.

Finally, we’ll bring you back into the city to explore the outskirts of town in the vast Washington Park.

From here you can mosy back down into the downtown and Old Town area to finish anything on your list from the first day.

Of course, we expect you’re going to want to come back to the city to finish everything on your Portland itinerary.

But at least we’ll give you the best the city has to offer in such a short amount of time!

Related: Don’t miss out on all of the best day trips from Portland !

Day 1 – Wander Historic Old Town and Downtown Portland

The first day of the Portland itinerary will begin in the historic Old Town. Known for its inclusion of Old Town Chinatown, this part of town covers a few city blocks along the Willamette River.

You’ll find everything from quirky shops, restaurants and bars to many unique local businesses.

If your plans include visiting Portland over the weekend then you will want to start your day at the local Saturday Market.

Every Saturday and Sunday between March and Christmas Eve hundreds of vendors will set up booths in Tom McCall Waterfront Park beneath the Burnside Bridge.

Find unique art, delicious munchies and a variety of entertainment as you stroll through the market for a uniquely Portland experience.

From here you’ll make your way up to the Chinatown Gates and the official entrance into Portland’s classic Chinatown. As a city within a city center, there are lots of shops to explore and food to enjoy.

One of the biggest Portland attractions in Chinatown are the Shanghai Tunnels. Officially known as the Old Portland Underground , the tunnels are a series of underground passageways connecting a variety of shops and businesses.

As they were first intended, these tunnels were a passageway for transporting merchandise from the docks on the Willamette River to the various storehouse and shops via their basements.

This led to the opportunity for organized crime and the practice of “shanghaiing,” which is essentially the kidnap and conscription of sailors against their will.

Of course, over time myth and lore blended with true history and today, there are a variety of tours offering a behind-the-scenes look at the Shanghai Tunnels.

After touring the Shanghai Tunnels, head over to a more peaceful part of Old Town and visit the Lan Su Chinese Garden.

Despite the hustle and bustle of the 25th largest US city, the gardens intentionally offer tranquility to its visitors.

Stroll through the gardens on your own time, sit for tea and learn calligraphy, learn to play the traditional Chinese board game Wei Chi or practice Yang Style Tai Chi.

To learn more about the Chinese influence in Portland’s history, double back to the Chinatown Museum.

Only open in the afternoon between Thursday and Sunday, the museum is proud to present a no-holds-bar portrayal of life for Chinese immigrants in the Pacific Northwest.

Cost : $12.95
Hours : 10 am – 4 pm (closed Wednesdays)
Address : 239 NW Everett St

If you haven’t already filled up at any number of shops or restaurants in Chinatown, this is a great time to fill up on the famous Voodoo Doughnuts.

Known as much for their delicious doughnuts as for the quirky names they give them, Voodoo Doughnuts is a staple to Old Town Portland Oregon.

But you can also grab a bite to eat at Portland City Grill, Mother’s Bistro and Bar and Kells Irish Restaurant and Pub , all within a block of each other.

If you’re a big foodie, you can even embark on an underground donut tour of Portland !

Spend the afternoon perusing books at Powell’s City of Books. The largest independent bookstore in Portland, Powell’s City of Books location in Old Town boasts an inventory of over 1 million books!

Get lost in the shelves or take a tour of the store. As a lover of books, we think the best thing is just to wander around in search of one particular book to see what other books turn up along the way.

And whenever you begin to get thirsty for a cold beer, head a few blocks further to Deschutes Brewery Portland Public House.

Enjoy a draft beer brewed in-house or sit down for a full meal as you recap the day and prepare for your next adventure.

Deschutes Brewery is one of Oregon’s proudest and most successful breweries and well worth a taste while you’re in the area.

At this point in the day, you can either plan to retreat to your hotel to rest up for the next day in this busy Portland itinerary or you can head out into the Portland evening for a night on the town.

You are right in the middle of everything the city has to offer at night so enjoy your time out while visiting Portland.

READ MORE: Use this itinerary to plan the perfect 3 days in San Francisco

Day 2 – Portland Mini-Excursion

On day 2 of your 3 days in Portland itinerary, you’re going to have the chance to get out of the city a little bit to reflect on why this part of the country attracts so many people.

You’ve likely already asked yourself what mountain is in the background as you have turned corners in walking throughout the city.

This towering mountain is Mt. Hood and is one of the unique ways in which Portland can be identified.

Located 2 hours through a spectacular drive through the Columbia River Gorge a day trip to visit Mt. Hood is beautiful from start to finish.

Join a tour or drive yourself out and enjoy spectacular views along the way. There are plenty of places to stop and hike.

If you don’t have your own wheels but want to get some to do the trip independently, then head over to the Rental Cars website to find the best value rentals in Portland.

And you’re going to definitely want to stop at Multnomah Falls, one of the most famous waterfalls in all of the US.

Multnomah Falls is the most popular of dozens of waterfalls in the area. Located in the Columbia River Gorge, the falls consist of two drops.

The higher falls is 542 feet that cascade into a pool which then drops another 69 feet to the bottom of the creek.

While the waterfall was geologically formed around 15,000 years ago, more popular legend says that it formed when a young Native American woman sacrificed herself by falling off the top in order to appease the Great Spirit and save her tribe from a terrible plague.

Upon her death water began flowing down the falls.

Regardless of its source, viewing the waterfall is well worth the visit especially when combined with several other waterfalls in the area.

This half-day tour is a fantastic way to get out there. If you love nature, definitely include this stop in your Portland itinerary.

If you are interested in wine, a quick trip to the Willamette Valley an hour south of Portland is definitely worth your time.

The soil in the valley is very fertile thanks to the volcanic activity that shaped this part of the country.

As such, combined with a climate perfect for growing grapes, there are now over a half dozen world-class wineries in Willamette Valley.

You can take a self-guided tour of the vineyards with your own vehicle. Or join a tour from Portland and don’t worry about how much wine you drink !

If you do have your own transportation, however, and are kicking yourself for having to choose between wine and waterfalls, don’t worry.

Silver Falls State Park is under a half an hour drive through beautiful landscapes and boasts over 20 miles of trails that will lead you to 10 different waterfalls.

You don’t have to hike them all, of course. Most waterfalls are quickly accessible from parking areas throughout the park.

This tour combines Silver Falls with Willamette Wine Country, so you can hit both in one trip. Wine country is also a great weekend trip, if you have more time and are really into wine!

If you have no desire, or means, to get away from the city during your 3 days in Portland, then you can still experience the great outdoors by spending a few hours hiking through Forest Park.

Covering over 5,000 acres, Forest Park has 80 miles of trails that you can hike, bike or jog.

Open from 5 am until 10 pm, you can spend as much or as little time exercising or simply enjoying nature that is tucked within the reach of Portland.

Depending on how far you ventured out during the day you are likely to want to come back to your hotel and rest up for your final day in your Portland itinerary.

But if you want to continue to try and sample all of the delicious craft beers in the city or want to catch a comedy show or concert, head back into Old Town or downtown Portland for the evening.

READ MORE: Use this itinerary to plan the perfect 3 days in Seattle .

Day 3 – Downtown Portland

Depending on how fast you moved through Old Town, you might have already skipped into downtown on day 1 of your 3 days in Portland itinerary.

But if you didn’t venture out yet there are a few places you should visit.

Start out at Voodoo Doughnuts on the fringe of Old Town. Then head two blocks to Tom McCall Waterfront Park .

If you’re here on a Saturday you can enjoy the Saturday Market . Otherwise, enjoy a stroll down the riverfront on the waterfront park trail, or browse the local businesses throughout town.

If you’re interested in history, then cross the street back over to the Oregon Historical Society. Here, among other things, you can see the penny that was flipped to determine the name of the city.

There are a series of other displays and revolving exhibits that highlight Oregon’s rich history.

Head another two blocks to the Portland Art Museum if you are interested in traditional art museums, with a particular emphasis on Native American, Asian and American arts.

Hours : 10 am – 5 pm (Closed Mon/Tues)
Address : 1219 SW Park Ave.

Or you can head just a few short blocks to the Pioneer Courthouse Square at the heart of the city of Portland.

Affectionately known as “Portland’s living room,” the massive square hosts a variety of over 300 events throughout the year.

The milepost sign is one of the most recognizable features of the square.

Though anyone who has spent any time passing through Portland, let alone living here, will tell you that they’ve attended festivals and concerts, markets, runs and races and political events in the square as well.

Be sure to check what events are taking place during your visit as there is almost guaranteed to be something going on during your 3 days in Portland.

At this point, you are in the perfect position to make another decision about how to spend the remaining time of your Portland itinerary.

If you enjoyed Old Town and Chinatown you are back on the cusp of entering those neighborhoods again. Be sure to check off anything you didn’t see or do on your first day.

Alternatively, if there is a soccer match taking place it will be at the stadium at Providence Park .

Portland is known for its soccer fanatics. So if there happens to be a match this will definitely be a unique way to take in a few hours.

Lastly, you can head up to Washington Park where a whole other world awaits you. Here over 140 hectares of city park invites you to explore the many activities in the park.

The Portland Japanese Garden has 12 acres featuring 8 different gardens and a magnificent view of Mt. Hood.

Enjoy the peace and tranquility the traditional Japanese garden offers, including a tea house and numerous walkways and streams that reflect the Japanese aesthetic.

Cost : $16.95
Hours : 10am – 3:30pm, closed Tuesdays
Address : 611 SW Kingston Ave

The International Rose Test Garden features over 10,000 rose bushes and 650 varieties of roses.

As Portland has been dubbed the City of Roses, the International Rose Test Garden receives roses from all over the world where they are evaluated on a number of characteristics.

With 4.5 acres and numerous gardens you can walk through and enjoy views of Mt. Hood.

Cost : FREE
Hours : 5am – 10pm
Address : 400 SW Kingston Ave

The Hoyt Arboretum invites you to wander through 12 miles of trails that traverse through over 2,000 species of trees and shrubs from 6 continents.

The arboretum invites you to enjoy the park at your own pace. But there are also guided tours and classes offered on the weekends where you can learn more about the species of plants in the park.

Address : 4000 SW Fairview Blvd

If you haven’t had your fill today, you can head over to the Pittock Mansion, a 46-room French chateau-inspired residence.

Completed in 1914, the mansion has a history of scandal surrounding the Pittock family.

But the size and beauty of the mansion is not to be diminished by its scandalous history.

(The Pittock Mansion is closed for the month of January 2022 for maintenance. Check the website for updates!)

Hours : 10am – 4pm, opens at 12pm on Tuesdays
Address : 3229 NW Pittock Dr

Just down the hill from Pittock Mansion is the Witches Castle. The remnants of a stone home built in the mid-1800s is all that remains, along with the lore of it’s one murderous owner Danford Balch.

Balch hired a helper to clear the land around the home. In the process, this helper fell in love with Balch’s daughter and eloped against his will.

Long story short, Balch murdered his daughter’s husband and after the trial he became Oregon’s first legal execution.

Today the home has been abandoned and moss has overgrown the building. It gained its name in the 1980s as groups of teenagers used the home to party.

It’s been a very busy 3 days in Portland and you’re likely going to spend the evening getting ready to leave the next day.

But if you still have some energy left, you could head across the Willamette River in downtown Portland and visit the Oregon Museum of Science and Industry’s Planetarium .

Cost : $6.75 – $7.50
Hours : 9:30 am – 5:30 pm
Address : 1945 SE Water Ave

If you do venture to this side of the river know that there is literally a whole other side to the city and you might stay up all night exploring the many bars and restaurants in the area!

READ MORE: Use this itinerary to plan the perfect 3 days in New York City

Portland Oregon Travel Guide

Now that you know how to spend 3 days in Portland Oregon, here is a little more information about when to visit the city, how to get around, where to stay and what to eat.

There’s not really a bad time to visit Portland, depending on what activities you plan to do when there.

The best time to visit is in the summer, when the weather is warm and it’s less likely to rain.

The city’s roses are in full bloom and outdoor activities are abundant. But the summer is also prime tourist season and you will need to book your hotel stay and tours in advance.

If you want to beat the summer crowds, plan on visiting March through May. You will still catch spring flowers blooming and it’s also a good time to whale tours on the coast.

The winter months from November through February are the rainiest and it can become quite chilly.

But if you are into winter sports, Portland is a great place for skiing and other winter activities because of its close proximity to Mt. Hood.

Though a big city, Portland is very compact for its size and is easily walkable and is one of the most bike-friendly cities in America.

Downtown Portland and the central city area are easy to explore on foot.

There are also several bike rental companies and a bike-share program if you’d rather bike around town.

Portland also has one of the best tourist-friendly public transportation services. Your best bet after arriving at the airport is to take the light rail train into the city or to your hotel, and for less than $3 it’s very budget-friendly.

There are several bus lines that can take you anywhere in the city and the Portland Streetcar is another popular option to get around town.

I wouldn’t recommend renting a car for exploring the city as parking can be very expensive. But do consider renting a car if you plan to visit Mt. Hood or Willamette Valley during your visit.

The best way to get around is to rent a car and explore on your own! We recommend Rental Cars , which has the largest range of vehicles for the best value on the market.

Where to Stay in Portland

Because most of the activities in this 3-day Portland itinerary center around the downtown area of the city, our recommendations for the best places to stay in Portland are all in this area.

There are a variety of options to suit any budget. But to make the most of your time in the city we wanted to save you transit time while providing you the best value in accommodation.

Here are our suggestions on where to stay in Portland.

Located just outside Old Town in the spirited Nob Hill neighborhood, HI Portland Northwest is the best place to stay in Portland if you are on a budget.

Choose between dorm or private accommodation and enjoy the shared kitchen, drinks at an in-house cafe and WiFi throughout the hostel.

HI Portland Northwest is located in close proximity to all public transportation and you can park on the street if you arrive in your own car.

This is the perfect location to explore Old Town and downtown Portland as well as to quickly access all of the activities of Washington Park.

The Hotel DeLuxe will give you a luxury feel at a mid-range price providing great value in your stay. With an on-site restaurant and bar, room service and their unique “Well & Fit kit” the hotel goes above and beyond to ensure you have everything you could want or need.

You can even partake in free fitness classes or borrow bicycles to get around the city.

Of course, being located in downtown Portland Oregon has its advantages too as you are right in the middle of everything we recommend during this itinerary.

Staying at the Society Hotel puts you in the middle of everything you could want to do during your 3 days in Portland itinerary.

Located just a quarter-mile from the famous Chinese Gardens and all that Old Town has to offer, the Society Hotel provides a fitness center, in-house restaurant and bar and offers complimentary breakfast to fill you up for your day out and about.

Rooms are spacious and come with views of the mountains or garden and include standard amenities to make your stay more enjoyable. Book the king suite for a truly exceptional stay.

Best Restaurants in Portland Oregon

Now for my favorite part of the whole post – where to eat in Portland!

You can never go wrong with a delicious doughnut at any hour of the day. A staple for everyone who visits or lives in Portland, Voodoo Doughnuts has several locations and is open 24 hours a day to make sure you get your doughnut fix.

Q Restaurant and Bar is a Portland favorite especially among those looking for a farm to table experience.

Enjoy traditional American cuisines of seafood, lamb, duck and good old fashioned steak all dressed up in delicious seasoning and preparations.

Serving up more fresh Pacific Northwest seafood than the name suggests, Jake’s Famous Crawfish is known for flying in its seafood daily.

Enjoy steelhead, Dungeness crab, and a spread of local oysters cooked into a variety of dishes.

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Lindsay Harvey

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PORTLAND Itinerary • MUST READ! (2024)

Be sure to check out our Portland travel guide to make sure you’ve got your hands on the best tips for traveling to Portland. We’ll guide you through every step of the way with this incredible Portland itinerary! Are you ready for the adventure to begin?

Portland is the largest city in the US, filled with a multitude of different cultures and colorful interactions. In the 1830s, a large number of people migrated to the Portland area to find their fortune! What once was a small village, eventually flourished into one of the biggest cities in the US!

During the 1940s, Portland became infamous as a hub of criminal activity. These were mainly illegal nightclubs, underground gambling dens, and other seedy activities. In the 1960s, Portland was exposed to the hippie community, which was the beginning of an even more diverse crowd for Portland!

So, why should you make Portland your next port of call? Well, its rich cultural history makes it the perfect place to spread your wings! As well as the wide range of activities you can indulge in while you’re there.

Hiking around the outskirts of town and then enjoying a delicious lunch at an alternative bistro is the ultimate Portland experience. Not thrilling enough for you? How about spending the day skiing on the icy mountain slopes? Let’s get started!

Unlock Our GREATEST Travel Secrets!

Best Time To Visit Portland

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If you’ve been wondering when to visit Portland, you’ve come to the right place. While there’s no wrong time to visit Portland, there’s definitely a season for everyone’s preferences. Portland summer runs from June to August and is a great time to visit as all the flowers are in full bloom. This being said, if you don’t like crowds, it’s best to stay well away from Portland during this time.

Spring in Portland runs from March to May, during this time the temperatures begin to rise, however you can still expect scattered rain showers throughout your trip. Spring is a great time to visit if you’d like to enjoy some warm weather and stay away from the crowds!

From September to November, Portland experiences Autumn. The temperatures start to drop and so does the price of accommodation. If you’re on a budgeted trip, this is a great time to visit this beautiful city.

Winter in Portland runs from December to February and is characterized by loads of rain! The temperatures are very low, but you’ll be happy to know that they rarely drop below freezing. The mountain peaks are covered in snow, making it a great time for a ski trip!

Pick your preferred weather, and keep reading to find out where to stay in Portland.

In order to round off your Portland itinerary, you’re going to need to plan where to stay in Portland during your trip. If you’re planning a short vacation, we recommend staying in a central location that allows for quick transportation to all of the main Portland attractions.

Downtown is a great place for first-time visitors to Portland! It’s overflowing with an indescribable vibe that will leave you wanting more. This area is famous for its street markets, its historically significant museums and galleries, as well as its fascinating street art. Everything about this area is Instagrammable in the best way possible!

If you’re looking for an area a little off the beaten tourist path, you might want to try a place that has become very fashionable with the locals. Nob Hill is an upscale suburb filled with all of life’s little luxuries! Tree-lined streets and Victorian-style houses are what this area is known for. If you decide to stay in Nob Hill during your time in Portland, you can expect to be visiting many restaurants, cafes, boutiques, and sophisticated bistros.

Now that you’ve got an idea of what type of neighborhood you’d like to stay in during your Portland trip, you can decide exactly which hostel or hotel would suit your needs best. Here are a few of our favorites!

Best Hostel in Portland – HI Portland

HI Portland is centrally located in the Nob Hill district which makes for easy access to many of the main Portland attractions. Located in a Victorian-style building, this very simple yet efficient hostel allows for a sense of community with its open communal areas. If you’re looking to meet up with like-minded travelers, opting to stay in this hostel is a great choice!

If you’ve got your heart set on staying in a hostel, take a look at our top hostels in Portland!

Best Airbnb in Portland – Downtown Home on the River!

If there’s one thing you should do when you visit Portland, it’s staying in a home overlooking the Willamette River. This room has an iconic view of the bridge in the background that you can have the pleasure of waking up in the morning. Often its quite cold in Portland, which is the best time to take a dip in the hot tub this place has access to all year round, with a fire pit and picnic table to enjoy on the deck as well! Did we mention blackout curtains? YEP! Get all the beauty sleep need because there won’t be any sunshine peaking through those windows to disturb you.

Best Budget Hotel in Portland – Ramada by Wyndham

The Ramada by Wyndham is conveniently located a mere mile from Portland Airport and offers a twenty-four-hour airport shuttle service to make travel a little easier for its guests! Casual on-site dining and a fully stocked bar are available for those who’d like to save a pretty penny on dining expenses.

Best Luxury Hotel in Portland – Hotel Rose

The Hotel Rose is located in the Downtown area, close to all the action, and provides a luxury stay for their guests. Each room is kitted out with its own kitchenette and bathroom, allowing for more privacy. The hotel has a beautiful restaurant and cafe area that means guests won’t have to travel far to get a great meal!

If you’re traveling to Portland, it’s important to figure out just how you plan to get around during your stay, because of the heavy traffic in this city, we recommend skipping the car rental to make life a lot easier (and cheaper) for yourself!

Tickets for buses, light rails, and streetcars will only cost you $5 USD for a whole day, making it a very affordable way to get around. The same ticket will work for the entire TriMet System. You can hop from light rail to bus, to streetcar the whole day without having to worry about buying another ticket. As you know, convenience is key to having a great holiday in Portland.

Many Portland locals use Uber to get around. It is very convenient, but it can get a little pricey if you’re on a budget. However, it’s still cheaper than using a traditional taxi.

Portland is a very bike-friendly town, in fact, it’s the main form of transport that the local use for short distances. There are rental stations all over the city making it extremely easy to locate a bike whenever you need one.

Now that you know how to get around Portland, let’s take a look at what activities you should be adding to your Portland itinerary.

On the first day of your Portland itinerary, you can expect to spend plenty of time in nature, as well as getting to know the locals a little better in their amazing public spaces. You’ll learn a lot about the city and its rich cultural history!

Day 1 / Stop 1 – Stroll Through Washington Park

Why it’s awesome: Washington Park is a public urban park and there are over 15 miles worth of walking/cycling trails in Washington Park, as well as many attractions.
Cost: Free!
Food nearby: Elephants Delicatessen is just a short drive from Washington Park and serves incredible gourmet foods. It also opens early in the morning which is helpful for those wanting to get an early start. They serve everything from burgers, deli meat and fish to cupcakes and pastries.

Washington Park expands over an impressive 410 acres of land and is home to many of Portland’s wildlife species. You’ll be sure to see a fair amount of thriving birdlife during your morning walk on this Portland itinerary.

With so many paths to choose from, it’s highly unlikely that you’ll manage to see the whole park in one morning, but no matter which path you take, you really can’t go wrong. The trees and flowers are always showing off, and you’ll feel at peace in your luscious green surrounds.

There are many Portland attractions in the park, a children’s museum, an arboretum and Japanese Gardens, some of which you’ll be exploring after your walk. If you’re in the mood for some stiff competition, feel free to make use of the free tennis courts in Washington Park.

Day 1 / Stop 2 – Visit the Japanese Garden

Why it’s awesome: The Japanese Gardens in Washington Park are absolutely beautiful, and they present many gorgeous photo opportunities.
Cost: USD $19
Food nearby: Bamboo Sushi serves certified sustainably sourced seafood, and it couldn’t be more delicious. After a morning learning about Japanese culture and enjoying the zen Japanese garden, sushi is the perfect way to end it off. However, if you’re not a sushi fan, there’s still plenty of dishes for you to enjoy. Everything from steak to sunny side eggs, there’s sure to be something for you!

The beautiful Japanese Gardens create an amazingly zen space within Washington Park. Once you’ve strolled through the well-kept miniature gardens, and moss-covered trees, be sure to visit the Japanese Cultural Village that sits on top of the hill in the Japanese Garden!

At the Japanese Cultural Village, you can immerse yourself in Japanese Culture and art, while learning about the many facets of their way of life! You can listen to the enchanting melodies being played on a harp and flute. You’ll also get the chance to learn about the art of kimono making and partake in a tea ceremony! All of which play an integral part in Japanese culture!

This activity will put you in the right mindset for the rest of your day, and leave you feeling at peace with the world around you!

Day 1 / Stop 3 – Enjoy the Company of Incredible Creatures at Oregon Zoo

Why it’s awesome: Oregon Zoo is one of the most famous of all the Portland attractions.
Cost: USD $18
Food nearby: Verde Cocina at Sylvan Highlands is a cozy restaurant that serves healthier options to traditional Mexican cuisine. You’ll find everything from steaks and salads to burritos and tacos, each with a distinctly Mexican flair! This is the perfect place to stop for lunch before heading to the next activity on your Portland trip itinerary!

If you’re an animal lover, this is an attraction you shouldn’t miss! This is by far the best place to come if you’re wanting to meet a variety of furry and feathered friends. This incredibly diverse zoo is home to more than 230 different animal species, including nineteen endangered species and nine threatened species, making it the largest zoo in Oregon.

The zoo is located in Washington Park, making it easily accessible to the public, and close to many other Portlands points of interest. The zoo was founded in 1888, making it the oldest zoo west of the Mississippi River.

The zoo also boasts an incredible plant collection, and puts plenty of energy into creating the right environment for each of its inhabitants!

Day 1 / Stop 4 – Explore Pittock Mansion

Why it’s awesome: The Pittock mansion was built in 1912 by Henry Pittock and his wife and is absolutely beautiful.
Cost: USD $12.
Food nearby: Papa Haydn is a romantic cafe that crafts European desserts to meet American-style sandwiches and salads. It’s the perfect place to stop for a burger lunch or an incredibly decadent slice of cake! This exquisite restaurant is more than just a place to have a meal, it provides an experience that no foodie should miss.

The Pittock mansion boasts incredible architecture and is the perfect space to do a bit of birdwatching. The mansion is built on a forty-six-acre piece of land, and there’s plenty of birdlife around.

The original Pittock couple that built the house moved into it during 1914 and only lived for another four years before their family took over the house. Their family lived in the mansion until 1958, before selling it to the state of Oregon in 1962.

The mansion was scheduled to be demolished, but local protesters stopped the demolition and it was later opened to the public in 1965. It now has 80,000 visitors every year!

The Pittock Mansion, now a museum, is dedicated to showing people the history of Portland and how this city turned from a muddy village into the industrial hub of Oregon, and then into the thriving city that it is today!

Day 1 / Stop 5 – Investigate Pioneer Courthouse Square

Why it’s awesome: Pioneer Courthouse Square has been lovingly named by the locals: Portland’s Living Room, and is a great place to socialize and get to know the locals.
Food nearby: Luc Lac Vietnamese Kitchen is a favorite amongst the locals and a must-try during your time in Portland. They serve authentic Vietnamese food and it’s absolutely delicious. Be sure to try one of their incredible noodle dishes! It’ll give you the energy you need to take on the rest of the day.

This 40,000 square foot courtyard has been lovingly renamed by the locals, as it’s become a local hangout for many of them. For many, it serves as a pedestrian footpath to simply get from one place to another, but there is so much more to this culturally vibrant courtyard!

You’ll notice a name carved into each brick, this is because the city needed funding to build the Pioneer Courthouse Square and came up with the idea of charging people $15 USD to get their name carved into a brick. These people have now become an immortalized part of the city!

There are many recreational activities to take part in, including outdoor chess tables- which makes for a great way to meet and get to know the locals.

Be sure to view the beautiful fountain that looks like a cascading waterfall, and visit the amphitheater just in case there’s live music to enjoy.

Day 1 / Stop 6 – Visit the Oregon Historical Society Museum

Why it’s awesome: You’ll get the chance to see the coin that was flipped to decide Portlands name!
Cost: USD $10
Food nearby: Jakes Famous Crawfish is the perfect place to end your day for any seafood lover! The decor is beautiful and gives the restaurant a very upscale feel! You can expect a myriad of unique dishes such as bacon-wrapped prawns, seafood soup, crayfish bowls, calamari plates, and seafood salads. Any dish you choose is guaranteed to be incredibly delicious. If you’ve worked up an appetite, be sure to splurge on dessert too as it won’t disappoint!

The Oregon Historical Society Museum is dedicated to making Portland’s long and interesting history accessible to all! They have put together many thought-provoking exhibits, that allow you to get to know Portland just a little bit better.

The museum contains many historical artifacts, including the very coin that was flipped in order to decide on Portland’s name!

If you’re interested in the history of the place you’re traveling to, this is a must-visit during your time in Portland . Be sure to take your time and explore every exhibit, as there’s so much to learn at this incredible museum.

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Forest Park | Powell’s City of Books | The Portland Art Museum | Oregon Museum of Science and Industry | Grixsen Brewing Company

During your second day in Portland, Oregon you can expect to see some great Portland attractions! You’ll start your morning off with a casual stroll through luscious natural surrounds and then explore a great big building filled with books, before heading on to many other adventures!

Day 2 / Stop 1 – Walk Through Forest Park

Why it’s awesome: Forest Park is a municipal park just outside of Portland.
Food nearby: The Meating Place Cafe is a cozy little restaurant that doubles as a meat deli. Don’t let this fool you, their food is incredible! Just a nine-minute drive from Forest Park, it’s the perfect place to come for a morning coffee or even an early breakfast! In the morning you can expect to be served a toasted sandwich, a breakfast burger, or even a waffle.

Forest Park is a beautifully overgrown and luscious park that sits just outside of downtown Portland! In 1860, Portland decided to create the municipal park in order to preserve its beautiful forests and create a big area for recreational activities such as walking, running, and cycling during your Portland itinerary adventures.

An early morning stroll through this luscious area is a great way to get your blood flowing and get energized for the day ahead. Be sure to keep your eyes peeled for the wildlife you’re likely to see during your walk! The forest is home to over 112 different plant species and over 62 mammal species!

Be sure to take your camera along for this trip as you’re more than likely going to be overwhelmed by the luscious forest and its shade-loving plants, as well as the multitude of wildlife you’re bound to see!

Day 2 / Stop 2 – Explore Powell’s City of Books

Why it’s awesome: Powell’s City of Books is a massive bookstore that stretches an entire square city block and reaches three stories high!
Food nearby: Oven and Shaker is a happening pizzeria that serves incredible wood-fired pies. A favorite amongst the locals, this cozy little restaurant never fails to amaze us! The pizza is great and the vibe is even better! Be sure to try one of their killer cocktails, we’re certain you’ll be coming back for more.

This incredible bookstore is so big you may just need a map to find your way around. But that’s why we love it! Getting lost in a ‘city of books’ is every reader’s dream. But you don’t have to be a bookworm to enjoy this immense bookstore!

Almost every day the bookstore hosts a reading by a famous author. It’s an incredible honor to watch one of these, so if you can coincide your visit with a reading, that would be ideal! If you’d like to tour the bookstore, you’ll need to let them know in advance. You can do this by simply emailing the store, and they’ll arrange for one of their friendly staff to show you around.

If you’re looking for a great read to enjoy on your plane ride home, this is sure to be the place to find it. So, keep your eyes peeled for a book that tickles your fancy!

Day 2 / Stop 3 – Discover a Masterpiece at the Portland Art Museum

Why it’s awesome: The Portland Art Museum is the oldest art museum in the Pacific Northwest, and it holds all the others to a very high standard!
Cost: USD $20
Food nearby: Fogo de Chao Brazilian Steakhouse is any meat-lovers dream! Expect to sit down for a delicious meaty lunch. They run an all-you-can-eat lunch special every day that helps to cut down on traveling expenses. If you’re not in the mood for a heavy lunch, don’t worry, there are plenty of delicious desserts to choose from!

At the Portland Art Museum, you’ll find Oregon’s most prestigious art collection! You can expect to find works from European masters, Japanese screen prints and American contemporary artworks, and that’s just for starters!

Once you’ve strolled through the incredible artworks inside the museum, you can visit the sculpture garden and the area devoted to photography. Each area has its own special charm and should be appreciated and observed with respect!

Delve deep into the art world and discover your favorite masterpieces from a previous century or this millennium. You’ll find it easy to get lost in the art at this museum as it stretched over the space of 3 separate buildings. For this reason, we recommend visiting their website and deciding on the exhibits you’re most interested in seeing before visiting the art museum!

Day 2 / Stop 4 – Explore the Oregon Museum of Science and Industry

Why it’s awesome: The Oregon Museum of Science and Industry is an interactive museum that’s filled with hands-on exhibits.
Cost: USD $15
Food nearby: PDX Sliders is an imaginative yet cozy restaurant that serves wonderful food. As you may have guessed, sliders are at the forefront of their menu and a hit amongst the locals. If you’re in the mood for a drink, they also serve the best local beers on the market, so be sure to give them a taste! PDX Sliders is the go-to place for all things comfort food in the Portland area!

If you have a keen interest in physics, science, chemistry, or paleontology, this is the perfect place to spend the day exploring and learning. Even if you don’t, these interactive and fun-filled displays make learning fun! It’s the kind of place you could get lost for hours.

If you’re a lover of all things ocean related, you’ll want to head to the USS Blueback display to see the most modern submarine on display in the US!

When you’ve had enough of the exhibits, be sure to see a show at the IMAX theater to get an incredible visual experience. The movies and documentaries that they show are constantly changing, so you’re sure to see something unique!

Day 2 / Stop 5 – Visit Grixsen Brewing Company

Why it’s awesome: Portland has a thriving craft beer scene, so why miss out on all the action!
Cost: Price varies depending on the tasting you choose.
Food nearby: Teote House Cafe is a happening Latin American Cafe that serves wonderful food until late at night! Enjoy absolutely delicious food while sipping on happy hour cocktails at this cozy joint. It’s also a great place to meet a few locals as it’s a favorite amongst those that live in the area!

A Grixsen is someone who always gives an honest effort to follow a righteous path and celebrates the good in everyone. It’s not hard to see what kind of company Grixsen Breweries is trying to be!

Grixsen was started by three friends who wanted to make a positive difference in their community, and that they did. Bringing the finest tasting beers to the modern experimental craft beer movement!

Celebrate the end of your second day in Portland with a very noble beer, and be sure to give their tasting menu a try. You’re sure to want to try more than one or two! Supporting local businesses while you travel is also a great way to give back to the community, showing your appreciation for their fine city!

HI Portland

HI Portland is centrally located in the Nob Hill district which makes for easy access to many of the main Portland attractions. Once you’ve booked your hostel, brush up on the basics of backpacking America.

24 Hour Reception

Doughnut Store | International Rose Test Garden | McMenamins Bagdad Theater and Pub | Dark Mini-Golf | Downtown Portland

If you’re going to be staying for more than three days in Portland, you’re going to need a few more activities to spice up your Portland trip itinerary. Here are a few extra Portland points of interest that are sure to make your holiday a hit!

Grab a Sweet Treat at Portland’s Favorite Doughnut Store

Enjoy Portland’s most unique doughnut flavors at their Voodoo Doughnut store.
Explore the mystical store and purchase some memorable merchandise.
Take photos of some of the wonderfully decorated sweet and savory doughnuts.

It seems that everyone that visits Portlands needs to have at least one doughnut from Voodoo doughnuts ! It’s a right of passage of sorts. Stop by for a sweet treat and a coffee before exploring the town and be sure to snap a pic. As they say, if you didn’t post it on Instagram, did it even happen?

Choose from a range of incredible flavors including the Voodoo Doll, Bacon Maple Bar and Portland Cream. All of which are worth a try. If you’re traveling with friends, be sure to order a box of different flavors and share it amongst you!

Be sure to buy some unique merchandise at the Voodoo doughnuts store. It’s the perfect way to immortalize your Portland trip with a memorable souvenir! After visiting the store, we’re sure you’ll fall under their witchy doughnut spell and be back for more!

Visit the International Rose Test Garden

If you love to stroll through beautiful gardens then this is the perfect activity to add to your Portland itinerary!
It’s best to skip the parking and arrive by walking, cycling, or by using a rideshare to get around. The parking lot is often full and it may take you a while to find parking.
Be sure to check out the public art while you’re in the rose garden! All public art was donated by local artists.

Portland’s Best Rose competition is held in the gardens each year, where judges from all over the world come to judge the roses in the International Rose Test Garden. This is a testament to the quality of the roses in this beautiful garden!

Be sure to check out the whole garden, in certain areas you’ll even be able to find fragrant roses that fill the area with a beautiful aroma! Unfortunately, you’re not allowed to pick the roses, but you can take photos to remember this beautiful place.

On the premises, you’ll also find a miniature rose garden that provides the garden with some of the cutest flowers you’ll ever see. This rose garden is well worth the visit and is a must add to your Portland itinerary!

Watch a Movie at McMenamins Bagdad Theater and Pub

Bagdad Theater was originally opened in 1927 and it has a distinctly old-timey Hollywood feel to it!
Sit back and relax with buttery popcorn as well as an ice cold beer while you enjoy a movie.
During its first year open, Bagdad Theater and Pub ran only silent films.

Visiting the Bagdad Theater and Pub, you’ll feel like you’ve stepped back in time to the early 1900’s! Although the Bagdad Theater and Pub has undergone many upgrades over the years, it has managed to preserve its authentic Hollywood feel.

The historical Bagdad theater has been a favorite amongst the locals for over 90 years and we believe will continue to be a hit for many more!

Be sure to check what movies are showing ahead of time, and to book in advance for the more popular films just to ensure you won’t miss out on attending this awesome theater! Stopping by at the pub for a bite to eat after the show is also a great idea. The Bagdad Theater and Pub is known for its great food, so don’t miss out on this tasty opportunity!

Play Glow in the Dark Mini-Golf

If you’re into unique sports, this just may be the game for you.
Decide whether you want to partake in a long or short game by choosing either the nine-hole or eighteen-hole option.
Play miniature golf under black lights on a 3D miniature golf course.

This is a great and memorable game to take part in, especially if you’re traveling with friends. A little challenge always makes the trip a little more exciting! Depending on the number of people playing, a full round generally takes about forty-five minutes to complete, so you’ll still have plenty of time in your day to enjoy other activities.

Glow in the dark mini-golf is also a great opportunity to get some really interesting photos while you make some incredibly unique memories! Although this game is usually played in groups of two or four people, you could always arrive and team up with a group there if you’re traveling along.

Be sure to book before you go as it gets really busy during certain times of the year, especially during school holidays. If you’re not in Portland during the school holidays, then don’t worry about booking as you’ll be able to show up and play whenever you like!

Explore Downtown Portland

There’s plenty to do in Downtown Portland, but it’s easily explorable by foot, which saves you money on public transport!
Exploring a neighborhood is one of the best ways to get to know an area and the people that live there. It opens you up to meeting new people and making friendships!
Downtown Portland is a fun mix of hipster bars and cafes, with arty boutiques and breweries thrown in the mix.

There really is something for everybody’s taste in Downtown Portland! Whether you’re in the mood for a shop-til-you-drop experience, or you just feel like strolling around and getting a feel for the area, you won’t be disappointed.

To make sure you’re getting the most authentic experience of Downtown Portland, be sure to eat at one of the many creative food trucks in the area. You’ll find them everywhere serving up a range of different cuisines. Locals tend to stop by for a bite to eat on their lunch breaks or on their way home from work, so why not join in the trend?

If you haven’t visited an art museum on your trip yet, be sure to stop by one of the many art galleries in the area. Whether it’s to spark the creativity in you or to just enjoy the art scene, you’re sure to find a gallery to suit your taste in Downtown Portland!

Portland is generally a very safe city to visit, and it’s unlikely that you’ll come across anything that’ll make you feel unsafe or even unwelcome in the great city, but that doesn’t mean you should be careless. When traveling, you should always take certain precautions to make sure you have a safe and undisturbed trip!

If you’re renting a car, be sure to hide your valuables out of site so that you don’t become the next victim of a smash-and-grab. Just like any other big city, smash-and-grabs happen from time to time.

Because so many people ride bicycles in Portland, bike theft has also become a problem. If you decide to rent a bike, make sure the rental shop gives you a proper lock for the bicycle, so that you can keep it safe even when you’re not on it!

Beware of overstaying your welcome in a parking space, or parking in a no-parking zone. Portland’s parking police take their jobs very seriously, and you could face a fine for staying just a few minutes more than your parking meter allows! Explaining that you’re foreign to Portland meter police doesn’t usually work either.

Be sure to check out other safety tips to make sure you stay safe during your tour of Portland!

Don’t Forget Your Travel Insurance for Portland

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

If you’re going to be staying for more than three days in Portland, we recommend adding a few day trips to your Portland itinerary! This is often the best way to squeeze in the most Portland points of interest during your travels. Here are a few of the best day trips you should be adding to your itinerary!

Wine and Waterfalls Portland Day Trip

On this eight-hour tour, you’ll start your in the morning by heading to the Columbia River Gorge. Here you’ll get the chance to stand at the foot of the second highest year-round waterfall in the U.S – Multnomah falls. This is one of the coolest hikes in Oregon.

You’ll then explore the rest of the Columbia River Gorge and see many other waterfalls along the way. After an exciting morning, ignoring the advice of TLC and waterfall-chasing with your experienced guide, you’ll enjoy an incredible lunch with wonderful views of Mt. Hood and Mt. Adams, while tasting fine wines.

Be sure to take your camera along for this Portland day-trip as this tour will provide you with many Instagrammable moments!

Mount Hood: Full Day Loop Tour From Portland

You’ll start your day with an early morning pick-up from the hotel. You’ll then be driven along a forested highway to the Mt. Hood wilderness , where you’ll stop to take a look at a few spectacular waterfalls! You’ll be taken to the best waterfall viewing spot, Benson Bridge, where you’ll be able to capture some incredible footage of the cascading waterfall!

Next, you’ll be taken to Hood River, a picturesque valley town, known as one of the best wind-sport destinations in the Portland area! You’ll get a chance to watch kiteboarders and windsurfers in action, before exploring the town a little further.

You’ll enjoy a bit of free time to explore Hood River, doing some shopping, having lunch, and doing a little wine tasting before heading home!

Oregon Coast Day Tour: Cannon Beach and Haystack Rock

During the eight-hour tour, you’ll get the chance to enjoy spectacular views of the dramatic Oregon coastline and the breath-taking Pacific Ocean. Your first stop will be Neahkahnie Point, which provides views of the massive expanse of ocean before you! It’s known as the best whale watching location on the coast.

You’ll then visit Short Sand Beach, which is a four mile stretch of beach, surrounded by luscious, temperate rainforest vegetation. After stopping for a walk and some photo-taking, you’ll head to Cannon Beach.

Cannon Beach is a small beach-side village that is easily walkable and fun to explore! You’ll get the rest of the afternoon to meander its pathways, enjoy its public artworks and photograph its beautiful flowers.

Eugene Highlights and Wine Tasting Combo

On this nine-hour tour, you’ll explore various attractions in the Downtown Eugene area. You’ll tour through the Shelton McMurphy Johnson house, which has been iconic in the Eugene area for over a century!

You’ll then explore the 400 different types of roses in the Owen Rose Garden , and then head to the University of Oregon for a tour of the beautiful campus. You’ll also get the chance to tour the Cascades Raptor Center, which has one of the largest collections of Raptor species in the Pacific Northwest!

You’ll then be dropped off in the Downtown area for lunch, before heading back to Portland.

Mount St. Helen’s Full-Day Tour From Portland

During this ten and a half hour tour of Mount St. Helen, you’ll get a few spectacular hiking opportunities. You’ll also get the chance to see the largest lava tube in the US! Along the way, you’ll learn a lot about the geology of the area, even visiting an old blast zone!

You’ll then visit the site of the largest landslide in recorded human history and learn how exactly volcanoes are now monitored.

Be sure to keep your eyes peeled during the tour, as elk, deer, beavers, otters, and an array of birds are all common sights on this tour.

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Find out what people want to know when planning their Portland itinerary.

Is Portland worth visiting?

Hell yeah! It’s full of incredible and rich culture, history and unique activities and sights. It’s also pretty off the beaten track too.

What are some fun things to do in Portland for adults?

Take a fun filled day trip exploring the Oregon coast . From beautiful places like Cannon Beach and Neahkahnie Point you can take in incredible and expansive views.

What are some family things to do in Portland, Oregon?

Washington Park provides a great day for all the family with a children’s museum, tennis courts, an arboretum and Japanese Gardens.

What are some great unique things to do in Portland, Oregon?

Portland is home to some wacky food creations at Jakes Famous Crawfish including things like bacon-wrapped prawns and crayfish bowls! Yum!

No matter what kind of vacation you prefer, we’re absolutely sure that Portland has something for you. Being such a big city, with such a vast population of people, there really is something for everyone’s taste!

If the big city life just isn’t for you, there’s plenty to do just outside of Portland. Luckily for every nature lover, Portland is surrounded by nature and has one of the biggest urban parks right in its center. This means you’re never too far from luscious vegetation and beautiful scenery. And, if you really like the outdoors, you can even stay at one of the stunning Eco-lodges in Portland where you can experience nature in Portland at its finest.

If you’re a thrill seeker looking for adventure, or you’re just looking for a break from mundane everyday life, Portland has plenty to offer . We hope you spotted some fabulous activities that you’d like to add to your Portland itinerary!

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

Aiden Freeborn

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The Perfect 2 to 3 Days in Portland Itinerary

Last Updated on February 20, 2024

by Kate Daniel

Disclaimer: This article contains affiliate links. That means if you click a link and make a purchase, we may make a small commission. As an Amazon Associate we earn from qualifying purchases. For more information, see our privacy policy.

Planning a 2 or 3 days in Portland itinerary can be an absolute joy when it comes to all of the cool and unusual things to do in this eclectic Oregon city. Echoing Austin — Texas’ hipster oasis — the Rose City’s motto, “Keep Portland Weird,” sums up its distinctive character, one affectionately satirized in the cult favorite TV show Portlandia .

But Portland’s quirkiness isn’t its only quality. Far from it. This modern metropolis, a gem of the Northwest, is also famous for its incredible food scene, eco-consciousness, gregarious locals, and much more.

If you’re planning a long weekend in Portland, read on to find some of the must-see attractions in this delightfully, proudly off-beat city.

Table of Contents

How Many Days in Portland?

Many would-be visitors to the Rose City will inevitably wonder how many days in Portland is enough to really do it justice and not feel too rushed.

Though it is Oregon’s largest city, Portland is also relatively compact and you can easily get a good feel for it in just a couple of days. With 2 days in Portland, you will have time to see all of the highlights in the downtown area and experience some of the city’s nightlife!

And if you happen to be visiting for a weekend trip, you can also have the opportunity to browse the Portland Saturday Market, which is considered to be the largest outdoor market in the USA.

If you have more time, consider spending another day in the city. Seeing Portland in 3 days allows you to venture further and maybe head out on a day trip from the city. However, there are plenty of things to do in Portland that you will be just as happy staying within the city!

Best Time to Visit Portland

Like its infamously rainy northern neighbor Seattle, Portland, too, upholds the Pacific Northwest’s cold, damp stereotype for much of the year. You’re almost guaranteed to see some rain, no matter when you visit.

Bring a jacket and, as long as you don’t mind standing out, an umbrella! Pacific Northwesterners are weirdly umbrella-averse. I don’t know why. It’s just how it is. We’ll walk in a literal downpour with our hoodie pulled way up over our beanie-clad head, soaking wet, and act completely unbothered. Don’t be like us; umbrellas exist for a reason.

However, it’s not all rain all the time. You can expect some days that exceed 90 ° F (32 ° C), chilly mornings, and cool nights on any given summer day in Portland.

Late spring, summer, and early fall are undoubtedly the best times to visit, not just because of the sunshine. It’s also when the rose, rhododendrons, and other flowers that line the city streets and urban gardens will be in full bloom, making the already-colorful city extra bright.

This is also prime time for outdoor events and festivals.

If you visit in winter, expect to be cold and wet (like, really wet). The good news is Oregon’s coast and near-coast region doesn’t usually drop to freezing during winter, meaning you should be safe from snow and ice. If you want that sort of thing, though, Mt. Hood isn’t far!

Driving along the Oregon Coast to Portland

Getting To & Around Portland

As its name denotes, Portland is and always has been a significant transport hub. But not just for seafarers. It’s also well-connected to the region via a train station, numerous buses, and an international airport. It’s also just under three hours’ drive from Seattle .

Portland is relatively easy to navigate. The MAX light rail from the airport to downtown takes about 40 minutes and costs about $2.50, or you can Uber or Lyft if you don’t have a car.

While traffic can be heavy, it’s not as bad when compared to nearby Seattle. Most people walk or cycle everywhere or take public transport.

The city’s stellar public transit network consists of MAX light rail, streetcars, and commuter rail, making it easy to get around Portland. If you’re going to stay within city limits, you really don’t need a car at all.

Most tourist attractions in the Rose City are located on the west side of the Willamette River and neighborhoods like downtown, the Pearl District, and Nob Hill. If your home base is in this area, you can walk or cycle most places.

The Rose City is famously bike-friendly, yet unlike some cycle-centric metropolises (Amsterdam), you’re not likely to get hit by a bike if you do prefer to hoof it. If you didn’t bring a bike, you could rent one for a few hours, the day, or the weekend from providers like Bike Town.

If you want to venture outside the city to the Oregon Coast or even down to San Francisco , which I can’t recommend strongly enough, a car will be helpful. You can rent one through Rentalcars.com if you don’t have your own.

Don’t fret if driving isn’t your thing, though! There are buses to some of the best destinations, like Seaside and Cannon Beach. A Greyhound from Union Station to Cannon Beach takes about two hours. Just be prepared to navigate a sporadic bus system once you get to your destination or walk/taxi everywhere.

2 to 3-Day Portland Itinerary

There’s always something happening in The Rose City, and you may find it hard to fit in everything you want to do in just one weekend. But if you do only have two days in Portland, here are a few stops you won’t want to miss.

Day 1 – Doughnuts, Bookshops & Museums!

Voodoo doughnuts .

The first stop is the city’s most famous and beloved doughnut shop, Voodoo Doughnuts , where you can grab a breakfast pastry and coffee.

Kenneth “Cat Daddy” Pogson and Tres Shannon, two entertainment-minded entrepreneurs, opened the first Voodoo Doughnuts in 2003. At the time, there wasn’t a single doughnut shop in downtown Portland, so you can imagine the craze that erupted when a shop as wacky as the city itself opened up and started serving up delicious pastries in a medley of classic and unconventional flavors.

Within a month, the shop had achieved a national press mention and a loyal, die-hard following at home. They’re now world-famous and an absolute must-stop on any Portland weekend itinerary.

If you’re still hungry or the line at Voodoo is absurdly long, head to Blue Star. While Voodoo’s patrons are about a 50/50 mix of tourists and locals, many Portlanders eschew the shop, insisting Blue Star is far better.

The lesser-known but no less tasty Blue Star serves up various tantalizing flavors, including Cointreau Crème Brûlée, maple bacon, Valrhona chocolate crunch, and The O.G., featuring an orxata (horchata) glaze.

If you’re really into your doughnuts you can even do a doughnut tour!

Powell’s Books

Powell’s Books is heaven for bookworms. The world’s largest independent bookstore, it is undoubtedly one of Portland’s most prized assets and another quintessential stop on a Portland, Oregon itinerary.

The shop spans an entire city block and is packed with a vast array of new and used books in every genre.

Grab a basket; you’ll need it to carry everything you pick up as you browse the labyrinth.

Powell’s is also famous for its rare book room, featuring rare first editions and signed copies of antique and contemporary titles.

After checking out, head to the café to rest for a bit and have a bite and a coffee. You’ll need to re-energize after spending a couple of hours wandering the store! And yes, you will probably be drinking a lot of coffee on your weekend in Portland. When in Rome…

An Afternoon at the Museum

Before heading out to get a taste of Portland’s vibrant nightlife, check out one (or both!) of the city’s most prominent museums.

The Oregon Museum of Science and Industry features various temporary exhibitions throughout the year and the Natural Science Hall, Empirical Theater, USS Blueback Submarine, and Kendall Planetarium.

Learn about everything from ancient natural history to contemporary scientific innovations and get lost in the mind-blowing vastness and complexity of the night sky.

Founded in 1892, the Portland Art Museum is one of the West Coast’s oldest art museums.

It features various temporary exhibitions featuring world-renowned artists in painting, print, mixed media, film, and more. The museum also houses permanent collections, including Native American Art, Asian Art, Northwest Art, European Art, American Art, and Photography.

Fancy a history lesson? Check out Pittock Mansion , which offers an immersive look at the city’s past in the setting of one of its oldest and most beautiful historic homes. The mansion also has a fantastic view of the city!

Enjoy Portland’s Nightlife

People joke that everyone in Portland is a barista, in a band, or both. And it’s not that far from the truth. There’s pretty much always a live show going on somewhere.

On your first night out, head to a venue or go bar-hopping and let yourself get swept into the vibrant nightlife scene.

Oregon Public House is a great place to start. The family-friendly pub, open from 4-9:30 p.m., donates all profits to local charities and is a popular meeting spot for non-profits. Start your evening with a delicious meal and a drink while giving back to the community in the process!

Then head to Alberta Street, the place to be for hip, local flavor. Start at Alberta Street Pub , a high-end establishment with a terrace perfect for sipping a cocktail on a summer evening. Then, stop by Radio Room , an art deco-themed bar with vegan treats and seasonal cocktails.

Next is Bye and Bye , a Southern-inspired bar with superb vegan cuisine. If it wasn’t clear by now, Portland is also one of the easiest places to be a vegan tourist!

Also on Alberta Street is Alleyway Bar, which is a bit grungy in the best possible way and often hosts live music.

McMenamins Crystal Ballroom, Revolution Hall, Alladin Theater, Dante’s, and Mississippi Studios are other hot spots for live music. Grab a copy of Portland Mercury to see what’s happening on any given evening.

Day 2 – Food Trucks, Parks & Arcades

Check out the food truck scene .

The Rose City is a foodie paradise, with a vast array of establishments from small cafes to Michelin restaurants.

For the second day of your time in Portland, grab brunch at a food cart.

Portland famously has the most strip clubs per capita of any U.S. city, about twice as many as public restrooms. But it’s also home to one of the nation’s biggest food truck scenes!

More than 600 food trucks throughout the city dishing up every kind of cuisine imaginable, from Korean to Ethiopian to and down-home barbecue to vegan pizza. Seriously, they have it all.

Unlike most food truck scenes, Portland’s are not mobile. Instead, they are organized into stationary “pods.” You can find a map of all the carts here , divided by categories to make finding your next meal a cinch.

You won’t get to try them all on your weekend in Portland, but you can try at least a few throughout the day! According to locals and critics, some of the best include Yoshi’s Sushi, Farmer & the Beast, Bing Mi, Matt’s BBQ, and Baby Blue Woodfired Pizza.

Washington Park

Next up on your Portland weekend itinerary is a stroll through Washington Park.

This urban green space is massive, with a zoo, arboretum, amphitheater, children’s museum, Japanese Garden, and International Test Rose Garden. The latter two are especially worth a visit.

The Portland Japanese Garden comprises 5.5 acres with impeccably landscaped greenery and water features, and a tea house.

The International Test Rose Garden features more than 10,000 roses in over 650 varieties of numerous colors and styles. This is reason enough to come in summer! June is peak bloom season, but there will likely be sweet-scented blossoms in late April through early October.

Ground Control

Want to feel like a kid again if you’re spending 2 days in Portland? Head to Ground Control , the family-friendly, nostalgia-inducing vintage-meets-futuristic arcade. It’s usually open from midday ‘til late.

With an arcade and video games, pinball machines, and a dance mat, it’s the perfect spot to spend a couple of hours on a rainy afternoon!

McMenamins

Next, grab a bite or a drink at McMenamins.

McMenamins is a local chain of family-owned establishments, primarily hotels, restaurants, and bars, located in repurposed or rejuvenated historic buildings. Each location is unique, with distinct features reflecting the city and its history.

McMenamins Kennedy School is one of the best. Located in a former abandoned elementary school, it might sound like the stuff horror movies are made of.

But there’s nothing spooky going on here unless there’s a scary flick showing at the in-house movie theatre. Besides the cinema, there’s also a hotel with unique rooms that evoke a sense of school-age nostalgia, a pool, a bar, and a brewery.

McMenamins Crystal Hotel, next to the Crystal Ballroom, in the Pearl District, the White Eagle Saloon & Hotel, and St. Johns Theatre & Pub are other popular McMenamins locales in Portland.

Day 3 – Day Trip from Portland

If you can spend 3 days in Portland, then there are a few great day trips you can take from the Rose City, if you’d like.

If the weather is nice, take advantage of the city’s status as one of the best spots for eco-tourism in the US!

If you’re craving something unusual and distinctly Portland, take a short but somewhat challenging hike up to Witch’s Castle. The “castle” doesn’t have anything to do with witches. But the abandoned structure has had many unpleasant lives throughout the past 150 years and is said to be haunted.

A bit further afield, there are multiple spots to check out the Pacific Northwest’s beauty along the Columbia River, at Multnomah Falls, Silver Falls, Hood River, or Mt. Hood.

A little further still, but so worth it, is the stunning Oregon Coast, with vast stretches of sandy, atmospheric beaches and quaint towns like Seaside and Astoria.

Where to Stay in Portland

If you’re looking for a great place to stay during your weekend in Portland, you really are spoilt for choice. There are countless great places to rest your head in the Rose City and if you’re looking for something great, check out these suggestions:

The Society Hotel – Situated within easy walking (or cycling!) distance of the Rose City’s top attractions, this chic hotel is perfect for those looking for a great place to stay. There are a number of rooms available and also a restaurant on site.

Kimpton Riverplace Hotel – If the life of luxury is more your style, then you can’t go wrong with this great hotel. Located on the banks of the Willamette River, there are a number of plush rooms available and countless other amenities to ensure your stay is a luxurious one.

HI Portland – Northwest – For budget backpackers or solo visitors, this hostel is a great choice for you. They have dorm beds and private rooms and there are also some great self-catering facilities and common areas to make meeting other traveller’s a breeze!

Private Rental – If you’re after a bit of privacy on your trip to Portland or would rather have a more “local” feel, then a private rental is the choice for you! There are a myriad of great properties in the Rose City, like this quaint, centrally located house .

Not quite what you’re looking for? Click here to browse more hotels in Portland!

Planning the perfect weekend in Portland itinerary really isn’t a hard task as there are so many amazing things to do in this Pacific Northwest city.

Are you planning to visit Portland? Have any questions about this itinerary? Let us know in the comments!

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About Kate Daniel

Kate Daniel is a writer for The World Was Here First. Originally from Washington State, she is a slow traveller and digital nomad who loves exploring both her own backyard and far-flung destinations. When she isn't writing, she is most likely befriending stray cats or daydreaming about the next adventure.

3 Days in Portland OR: The Ultimate Weekend in Portland Itinerary

Portland, Oregon is known the world over as one of the sweetest, friendliest, and most charming cities in the United States–and 3 days in Portland is definitely long enough to realize that the city lives up to that hype.

Jokes abound about how every Portlander is in a band and works at a bookstore and, well, Portland does have a thriving music scene and the world’s largest bookstore.

It’s a beautiful city full of parks, donuts, and good coffee, and a long weekend in Portland will no doubt include plenty of all of those.

Three days is just the right amount of time to a variety of the best things to do in Portland ; which includes the best food, parks, music venues, museums, and bookstores.

Here is everything you need to do and know for a perfect 3 days in Portland, Oregon.

Note: this Portland blog post was written for Our Escape Clause by Portland local Will Heath of Books and Bao . Thanks for joining us, Will!

Table of Contents

Day 1 in Portland Itinerary: The Pearl District
Day 2 in Portland Itinerary: Forest Park & Portland’s Japanese Garden

Day 3 in Portland Itinerary: The Northwest District

Alternative day 3 in portland itinerary: multnomah falls + mt. hood day trip .

Where to Stay for a Long Weekend in Portland, Oregon

Where to Eat in Portland OR

Getting around portland.

When to Visit Portland

Photo of steal sign stating "portland oregon" in front of a blue sky, a must-see during 3 days in portland or

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Day 1 in Portland Itinerary: The Pearl District

You can think of the Pearl District as central Portland, even though it isn’t actually in the middle.

This is the financial hub of the city, where all the high rises rise high and all the best shopping can be found.

The Pearl District is where Portland begins; it’s a short walk from the Willamette River which cuts the city in half, and it’s also where many of Portland’s most famous tourist attractions and must-visit places can be found, all within walking distance.

Its prime location and the huge number of attractions make the Pearl District the best place to start your 3 days in Portland itinerary, starting with the world’s biggest bookstore.

Tram in front of Union Tower in Portland Oregon, where you'll start your Portland 3 day itinerary in the Pearl district

Explore Powell’s City of Books, the world’s largest bookstore.

Powell’s City of Books is an enormous building. So big, in fact, that the front desk offers a free, and beautifully decorated, map to help you navigate through the world’s largest bookstore.

Powell’s is the pride of Portland. Locals and visitors alike cherish this enormous city-sized building that sells books both new and used, in every style and flavor you could imagine.

To really take it in, you need a good two hours to really explore and enjoy Powell’s. The shop is even famous for the fact that it provides baskets because they know you’re going to get carried away and gather more books than you can carry as you venture deeper into this labyrinth of books.

On the ground floor, Powell’s has a lovely little café, but we do recommend you leave that till last since it’s a great space to recuperate and flick through your newly purchased books with a flat white and a view of the bustling streets outside.

Powell’s offers new and used books, and you’ll also find sales on hardbacks that are now available in paperback. It’s very easy to find a steal here, both in the used section and in the sales. And, it being the biggest bookstore on the planet, Powell’s really does stock everything you could imagine.

When you finally reach the top, you’ll discover that Powell’s also has a rare book room that has been decorated like the musty old study of a college professor, complete with antique wooden desks and atmospheric lamp lighting. This room holds some incredible secrets, like rare first editions and signed copies of both antiquarian and modern books.

Photo of a man walking away from the camera down an aisle of bookshelves in Powell's City of Books, one of the first stops on this 3 day in Portland weekend getaway itinerary

Grab a donut at Voodoo Donuts.

Voodoo Donuts divides locals, mostly because it is so popular with tourists and locals spend their time loudly insisting that Blue Star sells far superior donuts. And while that might technically be true in terms of quality, Voodoo Donuts is such a fun experience that goes beyond just enjoying a good donut.

This world-famous donut shop is beloved amongst visitors to Portland thanks to the hilarious and charming novelty that is its range of strange donut concoctions and their delightful naming choices (some of which are certainly not appropriate if you’re bringing your kids along, so make your choice wisely).

There is an absurdly wide selection of donuts to choose from at Voodoo Donuts, and they’re all very reasonably priced (all cheaper than the locals’ beloved Blue Star). They’re also huge, ranging from a realistic but still bloated size to something that’s far more a cake than it is a donut.

Voodoo Donuts has some extremely friendly and accommodating staff; they know that so many visitors are first-timers and they’re happy to flex their knowledge about any and every donut on their roster. Just be warned that this place is intensely popular, and so it’s a smart idea to visit Voodoo Donuts in mid-morning or mid-afternoon to avoid the lunchtime rush.

Kate Storm Jeremy Storm and Jack Wodarski in Voodoo Donuts in 2014 in Portland Oregon

Walk across the Broadway Bridge and down the riverside.

There are an awful lot of bridges in Portland. They stitch the two halves of the city together across the Willamette River.

Broadway Bridge is a particularly iconic bridge, however, with it having the steel aesthetic of the Brooklyn Bridge and the red paintwork of the Golden Gate Bridge. It can also be easily reached on foot from the Pearl District since it begins just behind Union Station.

Getting up close to the industrial steel architecture of Broadway Bridge is akin to heading back in time to Portland’s industrial roots.

But far beyond that, once you’re up atop the bridge, you’ll find that it offers you a great view of the downtown Pearl District skyline and another of the rest of the river and neighboring bridges to the north and south. Broadway Bridge itself is an impressive part of Portland’s history, but the views that it offers are epic and worth admiring during your Portland weekend getaway.

From the Broadway Bridge, you can take a stroll up the waterfront on the Pearl District side. This is a long and tranquil walk that offers you beautiful and unique views of several different Portland bridges from the ground level.

Walking north, your right side will be river waves, massive cargo ships, and gargantuan overhead bridges. Your left side will be beautiful and fancy apartment buildings. And all the locals you’ll pass will be joggers and residents walking their dogs. It’s a perfect and peaceful afternoon stroll that encapsulates the friendly peace of Portland, as well as its rugged industrial lineage.

Broadway Bridge in Portland Oregon on a sunny day, a stop on this 3 days in Portland itinerary

Day 2 in Portland Itinerary: Forest Park & Portland’s Japanese Garden

Start your morning by heading straight to portland’s japanese garden..

Often and proudly touted as the best Japanese garden in the USA, Portland Japanese Garden is a huge area packed full of all the details and aesthetics that you’ll find in the very best traditional gardens in Japan . That includes wooden bridges over gentle streams, a tea house when you can enjoy fresh matcha tea, and a Japanese rock garden of raked stones and arrange rock pillars.

It’s easy to spend at least two hours exploring and relaxing at the Portland Japanese Garden. It’s an open and dynamic space that easily takes the top spot on the list of most beautiful places in Portland, especially on a clear blue day.

This is because clear blue skies allow the streams and waterfall to shimmer and offers an unparalleled view of Mt Hood in the distance. On a clear day, standing in the Portland Japanese Garden, the view of Mt Hood looks hardly any different to the coveted views you can get of Mt Fuji on a summer’s day in Tokyo.

Waterfall in Portland Oregon Japanese Garden, a relaxing stop during 3 days in Portland Oregon

… and then stop by the Rose Garden.

Beside the Portland Japanese Garden is a rose garden that can only be enjoyed in the summer months. While the Japanese Garden is open year-round, visiting in the summer is certainly the best choice if you also want to enjoy the bonus rose garden next door.

Beyond simply exploring the garden and enjoying some green tea at the teahouse, the Portland Japanese Garden also hosts frequent events that change week to week. These events range from musical performances that use traditional Japanese instruments, such as the koto harp, to traditional Japanese tea ceremonies and even lectures and mindfulness tours of the garden.

Visit Pittock Mansion, Portland’s most important historic building.

Pittock Mansion can be found just north of the Portland Japanese Garden and is a perfect stopgap on your way to Forest Park and the Witch’s Castle. The Pittocks, after which the mansion was named, were an influential Portland family who were largely responsible for turning the once small pioneer town into a thriving industrial port.

Their mansion was almost demolished back in the sixties but saved by the community. To this day it exists as a gorgeous piece of historical architecture in the form of a museum.

This gorgeous museum is Portland’s answer to Downton Abbey. Not only is it a real, tangible part of Portland’s history, but it’s also a simply gorgeous building to explore.

An enormous drawing room complete with a library, fireplace, chandeliers, and stunning furniture. A music room complete with harp, grand piano, and delightful details like sconces and tall windows looking out onto the grounds. A cool detail of Pittock Mansion is how the furniture and furnishings are all originals that were crafted by talented local craftsmen over a hundred years ago.

Pittock Mansion, a must-see when exploring Portland in 3 days

Explore the Witch’s Castle.

This is one of the most strange and unique things to do in Portland on this itinerary. The Witch’s Castle has nothing to do with witches at all, and neither is it a castle. And yet, it is undeniably a very unique and out-of-place structure.

The Witch’s Castle is a stone ruin that very much resembles a medieval European house. What’s so cool about this structure is not only its creepy, ghostly, ruinous stone structure but also the legend that surrounds it.

Where the Witch’s Castle now stands, a 19th-century man bought the land from another gentleman and then proceeded to elope with that gentleman’s daughter. The father was furious, and when the couple returned, the father shot the man dead in cold blood, and so the rumors of hauntings in the area began.

The Witch’s Castle is just one part of the enormous Forest Park, which takes up so much of west Portland’s landscape. You can start with the Witch’s Castle and then head north and hike through the varied landscape of forest park. Follow the Wildwood Trail, which will take you from the Witch’s Castle across several kilometers of rugged green wilderness.

Entrance to the Witch's Castle in Forest Park, which you'll see during your long weekend in Portland itinerary

Spend the afternoon exploring Portland’s street food scene.

After a morning and afternoon of visiting gardens and hiking across the natural landscape of Portland, you will have worked up one massive appetite. And, since Portland is famous for its wealth of international cuisine, especially in its food carts and street food options, there is no better option than to take a fabulous food tour of these legendary street food carts. These chefs are all amazing, and with this popular tour , you get to enjoy the best of them.

Book your street food tour in Portland today!

sausages and peppers sizzling on a grill at a portland oregon food truck

The Northwest District is a beautiful and semi-residential area of Portland and is home to many of the most picturesque and beautiful homes in the city. It’s situated between the downtown Pearl District and the wilderness area that contains Forest Park and the Portland Japanese Garden. It’s here that you can find some of the most unusual and exciting hidden spots in Portland.

Visit the Freakybuttrue Peculiarium and Museum.

This is easily Portland’s most unusual museum. The Freakybuttrue Peculiarium is an incredibly fun and unique Portland experience. Entry costs just $5 each, and when you first enter, you’ll be greeted by a ten-foot-tall sasquatch replica that you can hug and take photos with. From there, it only gets stranger.

The Peculiarium is a small museum that guides you from one strange experience to another. The whole place is filled with cheesy but fun supernatural ad science fiction gimmicks to experience and play with. There’s a doll’s house you can examine, with each room displaying a different horror element, like a bedroom with a ghost and a bathroom with a squid monster dragging a woman down the toilet.

At the Peculiarium, you can step into a room behind a curtain which feels like something out of The Twilight Zone; it shows you the inside of a human brain and encourages you to play along with a scripted mad science experiment. Then there’s a coffin you can get into which simulates being buried alive (don’t worry, it’s not actually scary at all).

This is a cheesy 50s sci-fi museum full of heart and silliness that embraces the weird and wonderful supernatural conspiracies of the world, from government experiments gone wrong to alien autopsies and, of course, Oregon’s own Sasquatch. There’s a lot of fun here to be had for just $5.

The author of this Portland blog post holding onto a sasquatch statue at the portland peculiarium

Wander down 23rd Avenue.

This north-south road will take you past some fantastic pitstops where you can grab a coffee and a snack on your way to another museum and a vintage cinema. Your first stop will be Blue Star, the donut shop which every Portlander will insist is far better than Voodoo Donuts. So, now is your time to finally try their donuts and decide for yourself which you prefer.

Your second pitstop is at Barista, one in a local chain of Portland coffee shops. Portland is second only to Seattle for its vibrant coffee scene, and the Barista chain of coffee shops represent the finest and fanciest coffee in Portland. Just down from Blue Star, you’ll find a Barista where you can either drink in or take a coffee out with you.

Enjoy an old movie at Cinema 21.

Take a left off 23 rd Avenue onto NW Irving St. Here, you’ll find every Portlander’s favorite movie theatre. Cinema 21 is a beautiful little independent and vintage movie theatre that plays classic American cinema from decades past. A few hours spent at this cinema is a very fun time.

Cinema 21 sells all kinds of snacks and beverages, including full pizzas and even local beers.

The Escape New York Pizza is delicious; pair this with a beer and a classic film in a comfy seat at a vintage cinema, and there’s no experience like it in all of Portland.

Street scene in Portland OR with a tram visible in the back right of the photo--Portland's public transport is one of the best ways to get around during 3 days in Portland!

If you’d rather get out of the city for the last day of your long weekend in Portland, why not take a day trip to Mt. Hood? From the Japanese Garden you will have spied this incredible snow-capped mountain, and now you can easily get there yourself.

This fantastic tour will take you there and back, with plenty of interesting stops like Multnomah Falls and views of the Columbia River Gorge, which are some of the best places to visit in Oregon .

If you’d rather not join a tour, you can also drive yourself there if you have a car of your own (more on driving in Portland below).

Either way, the greenery, waterfalls, and views you get once you’re up there are unparalleled and are an amazing way to close out your 3 day Portland itinerary.

Book your day trip to Mt. Hood & Multnomah Falls today!

Multnomah Falls near Portland OR in the early fall

Where to Stay for a Long Weekend in Portland, Oregon

As we’ve already mentioned, Portland is split in half by the river.

East Portland is a very wide open, quiet, and residential area. There are some lovely restaurants and cafes to visit, but most of the best tourist stuff that you’ll want to see and explore is all in west Portland’s Pearl and Northwest Districts. Therefore, these are the districts you’ll want to stay in.

The Pearl District is where most of Portland’s coolest hotels can be found. And the Northwest District is a more upscale, upmarket neighborhood of beautiful homes. You can find some great places to stay in both areas, and here are your three best options for budget, mid-range, and luxury hotel stays.

The only thing to know about the Pearl District before booking your hotel is that it has a severe homeless problem. Most of the city’s rough sleepers congregate in the Chinatown area of the Pearl District but, regardless, homelessness has become an increasing issue in Portland that is quite upsetting to see.

Kate standing in front of gate to Chinatown in Portland, OR

The Society Hotel — This is a very Portland hotel. It has a rustic hipster aesthetic of exposed brick and vintage aesthetic, but the service is top-notch, and the restaurant serves a local cuisine that’s as satisfying as it is filling.

Within walking distance from this hotel are some of the best attractions and sights in the city, including the picturesque Northwest District and all the unique features of the Pearl District, including the river and bridges.

Check rates & book your stay at The Society Hotel!

Park Lane Suites & Inn — Found in the upmarket and residential Northwest District, while still being within walking distance of the exciting Pearl District as well as the gorgeous Japanese Garden and rose gardens, this hotel is in the perfect location.

At a mid-range price, you get some beautiful décor and all the best amenities, including a large TV and wood furniture that soothes and makes you feel right at home during your long weekend in Portland.

Check rates & book your stay at Park Lane Suites & Inn!

Hampton Inn & Suites (Pearl District) — This gorgeous modern hotel is right at the heart of the action.

Powell’s City of Books and Voodoo Donuts are both just around the corner, as is all the best shopping in the city.

The hotel itself features an indoor pool, a rooftop terrace, and spacious sweets that feel more like a private apartment than a hotel room, making it the perfect choice for luxury travelers exploring Portland in 3 days.

Check rates & book your stay at the Hampton Inn & Suites!

Fountain in the Rose Garden, an excellent summer addition to a 3 days in Portland itinerary

Portland has a wonderful selection of great world foods, and many of them are east of the river but they are so worth the extra distance you may be able to justify the travel to get there–especially these few.

This is an authentic Indonesian restaurant that serves far more than chicken satay. The food is fresh and varied. From grilled fish to a thick and sweet beef curry, as well as pork dumplings to die for.

Bollywood Theater

This is an Indian restaurant owned by local Portlanders who have studied the cuisine until they became experts in Indian dishes, and it certainly shows. The paneer dishes, in particular, are exquisite, and they cook rice to perfection, better than you ever thought rice could be prepared

The Carts on Foster

This is an awesome selection of food carts in Southeast Portland. There are a total of seventeen, some of which are beer gardens and even hair salons.

But most are food carts that serve up delicacies from around the world, from Mexican to Scandinavian cuisine. If you want to try out Portland’s legendary food cart scene during your 3 days in Portland, this is the place to do so.

Vegetables cooking at a street food cart--a common sight on a Portland weekend getaway!

Portland has a fantastic public transport system. It’s not as good as that of New York City, but it is far better than cities like Los Angeles.

You can certainly get away with not having a car in Portland, especially if you are situated on the west side of the river, where the downtown district and all the city’s most fun places can be found. This part of town is easily walkable, so you don’t even need to rely on public transport.

If you are using public transport, however, the buses and trams work perfectly and are cheap to use.

Portland has a special transit app that you can download to your phone for free called the Hop Fastpass. You can top this up anytime and use it to get on any bus or trap with the tap of your phone; no cash requires. The buses go everywhere, and you can wait at any bus stop for no more than 15 minutes before a bus will turn up.

Having a car does make things a little easier, especially if you’re planning on taking a day trip out of the city to visit one of Portland’s waterfalls or hikes. In fact, if you are heading to Mt. Hood and don’t want to book a tour, having a car is a must. But a car can also be more hassle than it’s worth for a long weekend in Portland, especially downtown.

East of the river, parking on every street is free and easy, but west of the river there are meters on every street, and finding a place to park can be stressful. Relying on public transport is easier and takes away a lot of parking stress.

Columbia River Gorge as viewed from the side of the road

When to Visit Portland

Portland is one of the best places in Oregon and has something to offer regardless of the season. In winter, the snow will fall and in fall the foliage is breathtaking. However, the spring and summer months (anywhere between March and August) are still the best time to spend 3 days in Portland.

In the spring, Portland erupts with cherry blossoms that rival Tokyo’s hanami season. The cherry blossoms are on every street and transform Portland into a wonderland of vibrant pinks and whites. Combining this spectacle with a visit to Portland Japanese Garden makes spring in Portland better than spring in any other US city.

In the summer, the roses are in bloom, and a visit to the rose garden that’s found beside the Portland Japanese Garden is captivating.

This is also the time when the parks are full, the streets are bustling, and you can enjoy the fun of eating and enjoying coffee outside.

Strolls across the bridges and along the riverside, as well as hikes across Forest Park, are best enjoyed during the summer months.

4 photos of Portland Oregon: Rose Garden, Broadway Bridge, Powells City of Books, Japanese Gardens. Black text on a white background reads "how to spend 3 days in portland"

6 thoughts on “3 Days in Portland OR: The Ultimate Weekend in Portland Itinerary”

There also is Portland Saturday Market under the Burnside bridge. It’s in its 46th yr. Every weekend one can visit and see younic handmade items from several hundred venders.

I love Portland. One of the best kept secrets in America. I know you only had 3 days but only exploring the Westside was a mistake. That is where all the boring rich people live. 🙂 The Eastside is the heart of Portland culture. Its where Portlandia was born and continues to live. I recommend your readers spend at least one day visiting N Mississippi and Williams streets, the Alberta Arts District, NE Broadway, SE Hawthorn, Belmont and Division. The non-tourist spots where locals hang. Then you’ll know the real Portland.

Hi Sam! To each their own, but I do want to clarify that this post was not written based on the experience of spending 3 days in Portland, but was put together by a local Portland writer. 🙂

I agree, Sam. It’s a good itinerary, but no mention of the Eastside neighborhoods was disappointing.

Hi There! My boyfriend and I are planning on a trip to Portland in September. Do you have any recommendations on where to stay? Thanks!

Hi Arielle!

If you scroll back up, we have a section on recommended hotels in this blog post. 🙂

Hope you guys have a great time in Portland!

3 days in Portland itinerary for an epic weekend (2024)

Looking for the best 3 days in Portland itinerary for your visit?

You’ve come to the right place! Portland, the largest city in Oregon, is known for its vibrant arts scene, unique attractions, and a delightful fusion of trendy neighborhoods and lush green spaces.

Portland is also a great base for exploring famous places nearby like the Columbia River Gorge and the Oregon Coast.

I recently visited Portland as part of our Oregon road trip itinerary and spent a few days exploring the city and the surrounding regions.

I loved visiting all the downtown Portland attractions like Powell Books and Pittock Mansion, the trendy Portland neighborhoods like Pearl District and NW 23rd Ave. I was amazed at the attractions outside the city like Multnomah Falls and Oregon Coast.

My 3 day Portland itinerary will ensure you see the best sights in downtown Portland and explore its trendy neighborhoods.

You will also get to experience the most famous sights near Portland, like the historic Columbia Gorge and the magnificent Multnomah Falls. Also, no trip to Portland, Oregon, is complete without a visit to the famed Oregon Coast!

So get ready to experience the very best of Portland, the Columbia River Gorge, and the Oregon Coast.

In a hurry and looking for the best recommendations for your Portland Itinerary?

➡ Top Excursions in Portland:

Best of Portland Morning City tour – see the top city sights!
Half-Day Columbia River Gorge and Waterfall Hiking Tour – must-see!
Oregon Coast tour from Portland – Visit Oregon Coast and Canon Beach.
Willamette Valley Wine Tour – Tour wineries, includes picnic lunch.

➡ Below are my top recommendations for places to stay in Portland :

Downtown Portland: Hyatt Centric Downtown Portland
Northwest District: Inn at Northrup Station

➡ If flying into Portland, you will need a rental car . I recommend Discover Cars for the best rates!

3 days in Portland Itinerary

This Portland itinerary is jam-packed with things to do in Portland and nearby, assuming you have three full days in Portland. So ideally, you would have arrived the night before in Portland and be ready to start the next day.

If spending a weekend in Portland or a long weekend, plan to arrive Thursday night so that you have three full days to explore Portland and the surrounding areas.

Overview of Portland itinerary for 3 days

Day 1: Explore the sights of Portland downtown – Powell books, Pittock Mansion, International Rose Test Garden, Pearl District, Northwest 23rd Ave
Day 2: Experience the Historic Columbia River Gorge and its stops, and visit Multnomah Falls
Day 3: Head to the Oregon Coast and enjoy Cannon Beach.

Day 1: Explore Portland City

On Day 1 in Portland, explore the sights and attractions in Portland Downtown.

Some places, like Pittock Mansion and Washington Park, require a car due to their uphill location, while others are walkable and within Portland downtown.

Consider taking a city tour to efficiently cover all the sights during your limited day in Portland. Alternatively, self-guided exploration by car is also an option.

➡ Check rates and availability for this Best of Portland Morning City tour or Best of Portland Afternoon City tour , which covers the top sights. Perfect if you have limited time in Portland!

Pittock Mansion

We started our day in Portland by driving to Pittock Mansion in the morning, around 12 minutes from downtown by car. A small paid parking lot is available outside the mansion.

Perched atop a hill, this historic mansion offers the best views of downtown Portland. The mansion’s elegant rooms and exhibits delve into the city’s history. You can take a guided tour of the mansion for a small fee.

Portland city views from Pittock Mansion - Must visit in any Portland itinerary

Exploring the mansion’s grounds and enjoying downtown views is free. There is a seating area to relax and admire the city views.

Washington Park

Next, we went to Washington Park. Spanning over 400 acres to the west of downtown, Washington Park hosts diverse attractions, including the International Rose Test Garden, Hoyt Arboretum, Portland Japanese Garden, Oregon Zoo, and Oregon Children’s Museum.

Choose one to two attractions that interest you as Washington Park is quite large, and it’s impossible to see everything in a single day. We opted for the International Rose Test Garden , famous in this ‘City of Roses.’

International Rose Test Garden in Portland

The Rose garden was huge and spectacular. Thousands of rose varieties bloomed in vibrant colors during July, and the garden and walking paths were well-maintained.

On our next visit to Portland, we plan to explore Hyott Arboretum and its several hiking trails.

Portland Japanese Garden is also really serene and tranquil with its beautiful landscaping and koi ponds. We have a similar Japanese Tea Garden in Golden Gate Park.

Northwest 23rd Avenue

After exploring Washington Park, head to Northwest 23rd Avenue for lunch. Northwest 23rd Avenue, often referred to as “Trendy Third,” is known for its upscale boutiques, cozy cafes, and a mix of local and international restaurants.

The avenue is lined with beautiful tree-lined sidewalks and is great for a leisurely stroll. The street has an inviting atmosphere that captures the essence of Portland’s eclectic culture.

The architecture here is a mix of historic buildings and modern designs, giving the area a distinct and appealing vibe.

When it comes to dining options on Northwest 23rd Ave, there are several top-notch restaurants to choose from. Some notable ones include:

Blue Star Donuts – An artisanal donut shop that specializes in creative flavors and high-quality ingredients. It’s a favorite among donut lovers.

Papa Haydn – European-style cafe serving sandwiches, salads, entrees, and scrumptious desserts.

Grassa – Italian restaurant serving handmade pasta dishes! Some of the best pasta you have ever eaten!

Thai Bloom – Delicious Thai cuisine with curries, noodles, and rice dishes. We tried the Pad Thai, pineapple fried rice, and yellow curry, and everything was really good.

Matador NW Portland – Mexican restaurant and bar serving Mexican dishes and cocktails.

Bamboo Sushi – A sustainable and eco-friendly sushi restaurant that offers a delectable selection of fresh and responsibly sourced seafood.

Salt & Straw – A renowned ice cream parlor known for its innovative flavors and use of locally sourced ingredients. Expect creative combinations that cater to a variety of tastes.

Pearl District

Visiting the Pearl District offers a glimpse into Portland’s dynamic urban lifestyle and creative spirit. It’s where you can savor gourmet food and coffee, explore art galleries, and get a glimpse of the city’s upscale urban living.

Formerly an industrial area, it’s now known for its chic galleries, stylish boutiques, and a plethora of eateries.

Sidewalk in Portland lined with shops and trees

The neighborhood is a hub for contemporary art, with numerous galleries showcasing local and international talent. In the monthly art event called ‘The First Thursday Art Walk, ‘ galleries open their doors to art enthusiasts.

The Pearl District is home to several exceptional cafes and restaurants catering to diverse cuisines. A few top choices include:

Stumptown Coffee Roasters – A Portland institution passionate about crafting excellent coffee. Try the cold brew coffee here. It’s really good!

Caffe Umbria – A cozy Italian-style coffee shop known for its quality espresso and yummy pastries. A nice place to people-watch as well!

Andina – A Peruvian restaurant offering a fusion of traditional and modern dishes and a diverse cocktail menu.

Mediterranean Exploration Company – An upscale Mediterranean restaurant serving Middle Eastern dishes. It is a great place to eat with family and friends and share multiple dishes.

Oven and Shaker – Pizzeria serving great wood-fired artisanal pizzas and craft cocktails.

Powell’s City of Books

A must-visit in downtown Portland, Powell’s City of Books is among the world’s largest bookstores. My family spent a great amount of time here, and we bought several books to take home!

The bookstore spans an entire city block, housing a staggering collection of new and used books across multiple floors and color-coded rooms. They have a map to navigate the store! The third-floor Rare Books room is impressive with really unique and expensive books.

Aisles filled with books in Powells book store in Portland

The diverse book selection caters to every interest and genre, from rare editions to contemporary bestsellers. The cozy reading nooks and friendly staff make it a bibliophile’s paradise.

The Shake Shack restaurant opposite Powell’s is a great place to grab one of their gourmet smoothies and delicious burgers and fries.

Waterfront Park

In the evening, take a leisurely walk along the Willamette River waterfront, enjoying scenic city views and bridges. This scenic park offers a tranquil escape from the city’s hustle and bustle with its sprawling green spaces, tree-lined paths, and stunning riverfront views.

The Waterfront Park Trail starts at Burnside Bridge’s south end, ideal for strolling, cycling, or jogging along the river. The park hosts various festivals and events throughout the year.

Portland Saturday Market is a popular event on the weekends with local vendors selling handmade arts and crafts and food items.

Note: Downtown Portland has a noticeable homeless population, particularly near the waterfront. Daytime exploration generally feels safe.

➡ Check rates and availability for this 2.5-hour Dinner Cruise on Willamette River with live piano music and great food. Enjoy the city lights and views as you cruise on the Willamette River.

Day 2: Columbia Gorge, Multnomah Falls, Hood River

No trip to Portland is complete without a visit to the iconic Multnomah Falls and driving on the historic Columbia Gorge Highway.

On Day 2 in our Portland itinerary, we will venture out of the city, explore the Historic Columbia River Highway and its stops, and later visit the windsurfing town of Hood River.

If you are not planning to rent a car, you can also book a half-day tour from Portland to Columbia Gorge and the waterfalls.

➡ Check rates and availability for this highly rated Half-Day Columbia River Gorge and Waterfall Hiking Tour – Visit Multnomah Falls and other waterfalls and vista points on the historic Columbia Gorge Highway.

Historic Columbia River Highway Scenic Drive

Oregon is famous for its iconic waterfalls, and you will come across several of them on the Columbia River Hwy scenic drive.

This drive winds through Oregon’s Columbia River Gorge with stunning views of waterfalls, cliffs, and the Columbia River. This drive reminded me of the Road to Hana drive in Maui !

Only around 30 minutes from Portland, the historic highway runs alongside I-84 E, with several spectacular waterfalls and viewpoints. Take exit 22 on I-84 E and follow the NE Corbett Hill Rd to Historic Columbia River Hwy.

Below are the must-see stops on the historic Columbia River Hwy:

Portland Women’s Forum State Scenic Viewpoint

Named after the Portland Women’s Forum group that advocated for Gorge preservation, this viewpoint offers panoramic scenery of the Columbia River Gorge.

View of Columbia River and Vista House from Portland Women's Form viewpoint

From here, you will see the Vista House in the distance. We had a clear sky with incredible views on the day of our visit. I feel the picture above is postcard-perfect!

Vista House at Crown Point

Perched on Crown Point, the Vista House is a beautifully designed historic observatory that provides panoramic views of the Columbia River Gorge. It’s a perfect place to take in the awe-inspiring scenery and photos.

Latourell Falls

One of the first waterfalls you’ll encounter, Latourell Falls features a striking columnar basalt formation and a picturesque plunge into a pool below. A short 1-mile hike takes you to the viewpoint for an up-close look.

Bridal Veil Falls

A short hike from the highway leads to Bridal Veil Falls, where water cascades gracefully over a cliff, resembling a bridal veil.

Multnomah Falls

The most famous waterfall in the area, Multnomah Falls, is a two-tiered waterfall that drops 635 feet.

Cascading gracefully down a lush, forested cliffside in the heart of the Columbia River Gorge, this two-tiered waterfall is an iconic symbol of the Pacific Northwest’s breathtaking landscapes.

Multnomah Falls in Columbia River Gorge, Oregon

The lower tier has a large viewing platform. A short trail from here leads to Benson Bridge for a closer look at the upper falls.

Expect large crowds at Multnomah Falls, especially in summer. For I-84 parking during the busy summer months of May to September, you need to make a reservation on Recreation.gov . The historic highway’s parking lot doesn’t need a permit but is much smaller.

Note: The two parking lots at I-84 and Columbia River Hwy aren’t directly connected, and you will have to get on I-84 to access the larger I-84 parking lot.

Nestled in the heart of the Columbia River Gorge, Hood River is a charming town that offers breathtaking views of the river, lush landscapes, and the iconic Mount Hood.

Hood River is conveniently located about an hour from Portland and around 30 minutes east of Multnomah Falls via I-84 E. The drive from Portland to Hood River is very scenic along the Columbia River.

Hood River is known for windsurfing, kiteboarding, good food, shopping, and scenic river views. Whether you have a few hours or plan to stay overnight, there’s something for everyone.

Top Activities in Hood River:

Hood River Fruit Loop: This self-guided tour lets you explore charming orchards and farm stands. During harvest season, you can enjoy fresh produce, artisan foods, and U-pick experiences.

Hood River Lavender Farm: A picturesque stop where you can pick your own lavender bouquet and find various lavender products like oils, body items, and edible lavender.

Hood River Waterfront Park: Situated by the Columbia River, it’s an ideal spot for picnics, kite flying, or just relaxing by the water. The park provides breathtaking river views and pleasant walks along the water.

Windsurfing and Kiteboarding: Hood River draws windsurfing and kiteboarding enthusiasts due to the consistent winds and stunning Columbia River Gorge views. It’s captivating to watch the action from the waterfront park.

Local Wineries: Explore the Columbia Gorge AVA’s wineries, known for exceptional wines like Pinot Noir and whites. A wine tour will let you sample these offerings while enjoying the scenic surroundings.

Craft Breweries: Hood River boasts a lively craft beer scene with several breweries. You can unwind on their patios, savor seasonal brews, and soak in the town’s relaxed atmosphere.

Downtown Hood River: Hood River’s downtown area is filled with unique boutiques, galleries, and craft stores. You can find locally made goods, artwork, souvenirs, and restaurants.

Whether you’re passing through or planning a longer stay, Hood River promises a mix of outdoor activities, great food, and vibrant local culture.

If you have an extra day, Hood River is also a great place for an overnight or weekend stay.

Columbia Gorge Hotel and Spa is a wonderful hotel right next to the river. It has a spa, golf course, and a restaurant you can enjoy. Choose a room that looks out over the Columbia River!

Day 3: Oregon Coast

On your Day 3 in Portland, head to the famed Oregon Coast. Cannon Beach on the Oregon Coast is only a 1.5-hour drive from Portland, making it great for a day trip from Portland.

Below are your three options for a day trip to the Oregon Coast from Portland:

Drive to Canon Beach (1.5 hrs) and spend the rest of the day at the beach. This option has the least driving and more fun time at the beach.
From Canon Beach, drive south to Tillamook (1 Hour) and visit the Tillamook Creamery.
From Canon Beach, drive north to Astoria (40 minutes) and explore Ecola State Park along the way.

No matter which day trip you pick from the above three, you will be in awe of the stunning Oregon coast!

Oregon Coast is a great trip in any season. Visiting the Oregon Coast during winter is a whole different experience, with dramatic coastal storms and whale-watching opportunities.

Keep in mind that while these are some highlights, there’s much more to discover along the beautiful Oregon coast, and it would require at least a 3-day trip to explore the entire Oregon Coast from north to south.

Alternatively, if you do not wish to rent a car, you can take a full-day tour to the Oregon Coast from Portland.

➡ Check rates and availability for this highly rated small group Oregon Coast tour from Portland that takes you to Canon Beach and Haystack Rock and explore other coast attractions.

Cannon Beach

Cannon Beach is a scenic coastal town famous for Haystack Rock, a towering sea stack that graces the shoreline. Cannon Beach is one of the best places to visit on the Oregon Coast .

The beach is wide and has soft sand, so it’s great for walking, beachcombing, and watching beautiful sunsets. We visited a Wednesday morning in July, and there were many people on the beach.

It was a bit windy, but it was okay for us since we’re used to cold beaches in Northern California. Remember to wear layers of clothes for your trip along the Oregon Coast!

Wayfarer Restaurant & Lounge is right by the beach, where you can get delicious seafood for lunch.

If you need a place to stay, the Surfsand Resort is an excellent resort for families, and it’s right on the beach. They have comfy rooms and family-friendly amenities.

Tillamook Creamery

Driving from Cannon Beach to Tillamook Creamery takes about an hour and is a scenic journey along the Oregon coast. The route takes you through lush landscapes and charming coastal towns.

The Tillamook facility is enormous. It was very crowded on the day we visited. It was a Wednesday afternoon!

Upon arriving at the creamery, you’re greeted with a modern facility where you can learn about the cheese-making process, sample various cheeses, and enjoy freshly made ice cream.

Tillamook Cheese Factory on Oregon Coast

The creamery offers interactive exhibits, a gift shop with local products, and a viewing area to see cheese production.

They have self-guided tours as well as paid tours. The cafeteria has some great lunch options. We tried the deep-dish pizza, which was great!

Make sure to purchase some of their delicious ice cream. They have a lot of unique flavors here, not sold in stores!

Ecola State Park

Just north of Cannon Beach, Ecola State Park offers scenic viewpoints, forested trails, and rugged coastal panoramas. The Ecola Point viewpoint provides breathtaking vistas of the coastline.

You can stop here to take in some dramatic views of Cannon Beach and the coastline, or you can make it a longer stop and do a hike.

The Clatsop Loop Trail is a moderate 2.6-mile loop hike in Ecola State Park, Oregon, and is very popular. It forms a loop through the coastal forest, offering glimpses of the ocean. You will need around 2 hours for this hike.

Astoria is a small coastal town at the very northern end of the Oregon Coast, near the Columbia River. Astoria is around 40-minute drive north of Canon Beach.

Below are the top things to do in Astoria:

Columbia River Maritime Museum : Discover maritime history through exhibits and artifacts. Learn about shipwrecks, navigation, and the region’s seafaring heritage.

Astoria Column : Climb to the top of this tower for panoramic views of the town, Columbia River, and surrounding landscape. The column also features intricate murals depicting local history.

Astoria downtown : Stroll through Astoria’s quaint streets lined with Victorian houses, art galleries, and souvenir shops selling art, crafts, and specialty items. The town’s architecture and atmosphere offer a distinctive charm.

Seafood Dining : Indulge in fresh seafood at local eateries. Astoria’s coastal location ensures a delectable array of seafood options, from fish and chips to seafood chowder.

Cannery Pier Hotel & Spa is an excellent place to stay right on the Pier if you would like to spend a night in Astoria.

More Things to Do in Portland

If you have time, below are some more things to explore in Portland on your visit:

Pioneer Courthouse Square : Known as “Portland’s Living Room,” this central plaza hosts events and serves as a hub for people-watching, performances, and gatherings.

Food Truck Pods : Indulge in Portland’s renowned food truck scene, offering diverse cuisines and creative flavors in a casual outdoor setting. There are several food cart pods in Portland. The notable ones are at Pioneer Courthouse Square, Portland State University, Third Avenue, and Fifth Avenue. Stretch the Noodle is a very popular hand-made noodle food cart in the Fifth Avenue food cart pod.

Voodoo Doughnut : Satisfy your sweet tooth with a visit to this famous doughnut shop, known for its unique and whimsical creations.

Portland Art Museum : Immerse yourself in the city’s art scene by visiting this museum featuring an extensive collection of American, European, and Native American art.

Oregon Museum of Science and Industry (OMSI) : An interactive and educational science museum offering hands-on exhibits for all ages.

Craft Breweries : Experience the craft beer culture by visiting some of Portland’s renowned breweries and tasting rooms, known for their diverse and innovative brews.

Hiking in Forest Park : Discover the urban wilderness of Forest Park with its network of hiking trails, providing a serene escape from the city hustle.

Willamette Valley Wine Tour : Take a wine tour from Portland and visit some of the famous wineries and try pinots, chardonnay, and more.

➡ Check rates and availability for this highly rated small group Willamette Valley Wine Tour with a picnic lunch.

Where to Stay in Portland

With just 3 days in Portland, I recommend staying in downtown Portland so that you have more time to explore the city. There are some nice areas in Portland downtown that are quite safe to stay in.

Below are some great recommendations for your stay in Portland:

Downtown Portland

Hyatt Centric Downtown Portland – Situated in the heart of the city, the Hyatt Centric offers a convenient stay with modern amenities and easy access to downtown attractions. We stayed here during our visit to Portland and cannot recommend it enough!

Hills View from our room in Hyatt Centric

It was the perfect location to explore all the top sights in downtown Portland. The hotel is new and very modern and has a restaurant onsite. It also has valet parking privileges for a daily rate.

But what we loved about this hotel is the excellent and friendly staff. Everyone we met was awesome, with excellent customer service. We got a bed and breakfast rate and loved the made-to-order breakfast at the restaurant.

➡ Check rates and availability for Hyatt Centric Downtown Portland

Northwest District

Inn at Northrup Station is a great mid-range all-suite hotel in the trendy Northwest District of Portland. The hotel has free parking and complimentary breakfast.

Walk to all the restaurants and stores on NW 23rd Avenue and to the metro station.

➡ Check rates and availability for Inn at Northrup Station

Canopy by Hilton Portland Pearl District is located in the upscale and urban Peral District with trendy cafes and amazing restaurants. This modern hotel has valet parking and a restaurant onsite.

➡ Check rates and availability for Canopy by Hilton Portland Pearl District

Travel Tips for Visiting Portland

The travel tips below will help you plan and make the most of your visit to Portland!

When is the best time to visit Portland?

The best time to visit Portland is during the mild and dry months of summer, from June to September. This is when you’ll experience pleasant weather, vibrant outdoor events, and the blooming of the city’s iconic rose gardens.

September is a great month to visit, with fewer tourists compared to the summer months, and the weather is still pleasant.

How many days to spend in Portland, Oregon?

Spending around 3 to 4 days in Portland would allow you to explore the city’s main attractions, enjoy its diverse culinary scene, and possibly take day trips to nearby natural wonders.

How to get to Portland, Oregon?

Portland is accessible by air through Portland International Airport (PDX), which serves both domestic and international flights. It’s also well-connected by road and rail.

How to get around Portland, Oregon?

Portland has an efficient public transportation system, including light rail (MAX), buses, and streetcars. Biking is popular too, thanks to its bike-friendly infrastructure. Ride-sharing services and walking are also convenient options for getting around the city.

You will need a rental car if you wish to take day trips from Portland to Multnomah Falls, Columbia River Gorge, or Oregon Coast. I recommend checking out Discover Cars for the best rates!

Alternatively, you can also take day tours from Portland to nearby attractions.

What to pack for a trip to Portland?

Pack comfortable walking shoes, layers for changing weather, a rain jacket or umbrella, and a reusable water bottle. Don’t forget to bring your camera, as there are plenty of picturesque spots to capture.

Is Portland worth visiting?

Absolutely, Portland is worth visiting! With its unique blend of urban culture, trendy neighborhoods like Pearl District and Northwest District, culinary delights, lush green spaces like Washington Park, and easy access to natural attractions nearby like the Oregon Coast and Columbia River Gorge, Portland offers a well-rounded and memorable travel experience.

Is Portland safe?

Portland is generally considered safe for visitors, but it’s important to be aware of certain aspects.

One noticeable concern is the homeless population, which is visible in parts of the city. While most homeless individuals are not a threat, exercising caution and avoiding confrontations is recommended.

Certain areas of the city, such as Old Town/Chinatown and some parts of East Portland, may have higher instances of homelessness and associated challenges.

While these areas might be best approached with caution, it’s important to note that the majority of Portland remains safe and welcoming for tourists.

We stayed in Portland downtown and felt very comfortable exploring it during the day. Overall, staying vigilant and adhering to common safety practices is advisable when exploring any urban area.

Final Takeaways: Portland Itinerary for 3 days

In conclusion, this 3-day Portland itinerary offers a balanced mix of city exploration and captivating day trips.

From uncovering the city’s attractions to venturing to Multnomah Falls, Columbia River Highway, Hood River, and the Oregon coast, this itinerary ensures a well-rounded experience of the diverse beauty and attractions that Portland and its surrounding areas have to offer.

I hope you have a great time exploring Portland and and its breathtaking surroundings!

More about Portland and Oregon

Make sure to read other posts from my Portland and Oregon series!

Portland city views from Pittock Mansion - Portland is a must visit in any Oregon road trip itinerary

Best Oregon Road Trip Itinerary for 7 to 10 days

7 Best Bed and Breakfast in Ashland, Oregon

Anu Agarwal is the founder and author of vacation travel blog Destination Checkoff. Anu, a Northern California resident, and a regular nine-to-fiver, loves to vacation with her family to destinations all over the world. She is obsessed with doing endless research for her trips. She has traveled to several destinations in the United States, Canada, Mexico, Europe, and Asia. With her blog, Anu is excited to share her destination itineraries and vacation travel guides and help you check those dream destinations off your bucket list!

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Portland Itinerary: Plan a Perfect Weekend in Portland, Oregon

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Hip, funky and fun, Portland, Oregon is a perfect weekend destination! Boasting abundant green space, cool urban districts and a fabulous foodie scene, travelers visiting Portland in a weekend can truly experience the best of the city. Our Portland Itinerary features the top highlights – and visitors to Oregon can use our outline to create their Best Weekend in Portland trip plan!

Weekend in Portland Itinerary

Spending a weekend in Portland, Oregon is an excellent way to get acquainted with the city that so proudly proclaims to be weird. With a relaxed atmosphere and creative culture, visitors can get a good feel for Portland even in a short amount of time. From peculiar sights to natural attractions, visitors will find there is plenty to do on a weekend trip to Portland.

Planning a Portland Weekend Itinerary

On my first weekend trip to Oregon (and my very first time to the Pacific Northwest), I traveled to Portland to visit my cousin. Being in the company of a local, I wasn’t tasked with creating my own Portland, Oregon itinerary; she knew all the best places to go and had insider secrets. On that trip, I spent two days in Portland – and absolutely fell for the city.

Not long after my initial trip, I was itching to go back to discover even more. My cousin had since moved, so I took on the complete responsibility to plan a trip to Portland, Oregon from beginning to end. Intent on expanding my exploration, I created fun weekend trip itineraries that included the must see Portland sights, beautiful nature and the best food.

Based on diligent research and my experiences from several visits, we have created a 3-Day Itinerary Portland that is perfect for weekend trips!

3 Days in Portland, Oregon Itinerary: A Long Weekend

In our weekend trip planner for Portland, we outline a day-by-day plan for visiting Portland in 3 days.

It is assumed that you will arrive mid-afternoon on Friday (or Saturday) and stay until the evening on Sunday (or Monday). Although our Portland weekend itinerary does include a few ‘weekend only’ events, those activities can easily be substituted for weekday Portland adventures.

Therefore, this itinerary for Portland, Oregon can really be used for a trip over any days of the week!

A Longer or Shorter Trip to Portland, OR?

Furthermore, we understand that not all travelers are planning a Portland, Oregon 3-Day Itinerary. Some visitors are limited to just one day in Portland, while others may be creating a 5-Day Portland Itinerary.

To help fellow travelers, we offer suggestions for alternate Portland trip itineraries at the end of the article. Whether you are planning to see Portland in a day or are devising a longer Portland trip itinerary, you can use our tips to plan your ideal vacation to Oregon.

Looking for more to do in OR State? Use our guide to the Best Things To Do in Oregon .

How To Spend a Perfect Weekend in Portland, Oregon by JetSettingFools.com

In our trip plan, we have outlined how to spend 3 perfect days in Portland. In addition to our day-by-day plan for a weekend trip to Portland, Oregon, we also include a useful map of attractions and essential tips – like how to get there, where to stay, when to visit Portland and what you will need to pack.

Save, Bookmark or Pin our Portland Travel Guide to plan your trip to Oregon!

Day 1 Of Your Portland Weekend Trip

On Day 1 of your Portland 3-Day Itinerary, get settled into your accommodations (suggestions below), then set out to discover one of the city’s most vibrant districts, Pearl.

How To Plan a Weekend in Portland Oregon by JetSettingFools.com

Pearl District Portland

The Pearl District is an absolute must in every Portland, Oregon vacation itinerary! Once the warehouse district, the Pearl has evolved into a stylish enclave of residences, art galleries, green parks and some fabulous Portland restaurants.

Powell’s Bookstore

Start your exploration of the Pearl District at the landmark Powell’s City of Books, which is the largest independent bookstore in the world. The massive bookshop covers an entire city block and ranks on many lists as one of the Top 10 Bookstores in America.

Things To See in Portland Pearl District

After perusing the selection of books, take a walk through North Park Blocks, a green urban oasis since 1869.

Make your way through the Pearl District, walking north on 11th – the best street in Pearl District – passing boutique shops, cafes and restaurants along the way. Walk through Jamison Square, which features fountains where you can cool your feet in the summertime, stroll through the wetland habitat on the raised boardwalk in Tanner Springs Park.

At The Fields Park (which has a great play area for visitors planning a Kid Friendly Portland Itinerary), hop on the Willamette River Greenway Trail and make your back south to Chinatown and Old Town Portland.

Discover Old Town Chinatown Portland

Make your way into the Old Town Chinatown District. Although not as impressive as other American Chinatown districts – like San Francisco – there is an ornamental gate (at NW 4th Ave and W Burnside St) and a handful of other sights to include in your Three Days in Portland Itinerary.

Things To Do in Portland Chinatown

The highlight of Chinatown – and one of the absolute best things to do in Portland – is the lush Lan Su Chinese Garden.

Other attractions in the district to add to your Portland Itinerary are the Steel Bridge (a double-decker bridge built in 1912) and Union Station (the city’s main transportation hub, which was built in the late 1800s and is listed on the National Register of Historic Places).

Portland Underground Tunnel Tour

The Shanghai Tunnels are a fascinating place to see during your weekend in Portland. The guided tours depart multiple times a day, taking visitors into the subterranean space to learn about the history of the old tunnels and the ghosts that reside in them. Book it here!

Ground Kontrol Classic Arcade

Ease into the evening with a barcade experience at the classic Ground Kontrol Arcade. Patrons can play favorite retro games while sipping a beer. It’s the best place in Portland to get your pinball on!

Evening Entertainment: Dinner, Drinks and Live Music in Portland OR

There are many different ways to spend the first night of your Portland weekend – so where you end up will depend on your style and mood.

Personally, we think the PNW craft beer scene is not to be missed. However, downtown PDX has a stellar dining scene – especially in the rooftop perches above the city. Additionally, there are historic spots, cozy corners, international eats and plenty of live music.

We are highlighting a few of the best places to go in Portland, OR on your first night.

Portland Craft Beer

Nicknamed ‘Beervana,’ Portland claims to have more breweries than any other city in the world – so getting a taste of locally produced craft beer is practically essential during your 3 days in Portland.

The Pearl District is home to a range of restaurants and some of the best breweries in Portland. Among the many, our favored spot is Deschutes Brewery and Public House – for both food and craft beer. The menu is elevated pub grub and the fresh beer – of which there are 26 brews on tap – is exceptional.

Brewery Crawl and Cocktail Hop in Portland

From Deschutes, visitors can create their own Portland brewery tour, making stops at 10 Barrel Brewing, Backwoods Brewing Company and Von Ebert Brewing. For handcrafted cocktails, try Teardrop Lounge and Abigail Hall.

Looking for a fun activity for your girls’ or guys’ weekend in Portland? Discover the best craft beer on a mid-day craft beer tour !

Dinner and Drinks with a View in Portland

Travelers who would rather include fine dining and fancy cocktails in their Portland Itinerary have some superb options, too.

Portland City Grill is an exceptional restaurant that offers 360-degree views from their 30th floor location in the US Bancorp Tower. In fact, if you arrive early enough, you can partake in the phenomenal happy hour specials – all while enjoying the panoramic views over Portland.

For after dinner cocktails and city lights, head up to one of the best Portland rooftop bars – like Departure Bar, XPORT or Tope (where they also have excellent tacos!).

Historic and Cozy Vibes

One of the best things about spending a 3-day weekend in Portland is the quirky and cool establishments that dot the cityscape – and Huber’s Café is one of them.

Dating to 1879 and boasting a unique ambiance, Huber’s is one of the best places to eat in Portland. From the popular roasted turkey dinners to their famous Spanish coffee, Huber’s is a good choice for happy hour, dinner or a late night snack.

After a meal, head for the cozy but chic Multnomah Whiskey Library, where bottles line the shelves along exposed brick walls and leather chairs face a roaring fireplace.

Tea and International Fare

Portland might be famous for beer, but you certainly don’t need to drink in Portland to have a good time.

Start with an early evening tea flight at Smith Teamaker, then indulge in international fare at one of the best Asian restaurants in Portland. Top picks are Thai Peacock Restaurant, Masu Sushi or Luc Lac Vietnamese Kitchen.

Portland Live Music

If live music is your jam, check out who is playing at the historic McMenamins Crystal Ballroom, which has seen a slew of acts grace its stage since the early 1900s.

Alternatively, see what is happening at The Armory Theater (aka Portland Center Stage) for an intimate and entertaining performance. Just don’t stay out too late, because tomorrow is another full day of fun!

Day 2 Of Your Weekend in Portland Itinerary

On the second day of your Three Days in Portland Itinerary, start with some classic Portland food experiences, then see Downtown Portland sights. End the day across the Willamette River exploring the distinctly different districts in East Portland.

How To Spend 3 Days in Portland Oregon by JetSettingFools.com

Stumptown Coffee Roasters

The city’s coffee craze is serious business – and Stumptown Coffee is the place to experience it on your weekend in Portland, Oregon. A local Portland favorite since 1999 (although now owned by Peet’s Coffee), Stumptown embodies the Third Wave Coffee Movement.

Voodoo Doughnut Portland

In 2000, Voodoo Doughnut opened in Portland, OR…and so the doughnut craze began. With a line of creative flavors – like Bacon Maple Ale – the shop quickly made headlines and their Portland Cream Doughnut has been proclaimed the city’s official doughnut. Who ever knew there was such a thing?!

Patrons line up out the door and down the block everyday for the sugary breakfast treats – and on your weekend in Portland, you should join the crowd!

More Portland Donuts

Visitors who don’t want to stand in line, but still want a darn good doughnut, might want to check out Blue Star Donuts instead (although there are sometimes lines here as well). Their gourmet donuts include flavors like Blueberry Basil Cake and Mexican Hot Chocolate.

However, for a classic donut experience, make your way to Pip’s Original Doughnuts and Chai. The old-fashioned donut shop will likely have a line, but it’s worth it for the freshly fried donuts that are melt-in-your-mouth delicious. Oh – and they taste best with a flight of chai teas!

Pro Tip : If you really want to go crazy, try donuts from multiple spots. Or, better yet, join a guided Donut Tour during your three days in Portland, Oregon.

Portland Saturday Market

Recognized as the longest running outdoor arts-and-crafts market in the US, the Portland Saturday Market is a must-see on your weekend getaway to Portland, Oregon. Opened in 1974, the free outdoor market features nearly 400 local vendors – plus there is always live music and heaps of international food truck options.

Pro Tip : Wander from the market north under the Burnside Bridge where you have the best view of the famous neon White Stag Sign – a must-see Portland, Oregon landmark. (Look for it on the north side of the bridge on Couch Street).

Downtown Portland Bike Tour

Cycling is a popular mode of transport in the city – which is why taking a spin on two wheels is one of our top Portland trip ideas.

In the afternoon, hop on a bicycle for a guided tour of Portland downtown attractions and districts. Biking is one of the best ways to get around Portland – and on the tour, you can learn more about the city’s history as you pedal through the streets. Portland sightseeing on the route includes Pioneer Courthouse Square, Tom McCall Waterfront Park and Fifth Avenue Food Cart Pod. Find out more!

Another Popular Portland Tour

Alternatively, visitors interested in learning more about the food culture can add a Portland Food Tour to their Portland 3 Day Itinerary. The small-group walking tour includes 5 food stops at some of the best Portland restaurants and food carts. This tour is limited to just 12 people, so reserve your spot in advance !

Explore a Fascinating District in Portland’s Eastside

By mid-afternoon of your second day of your Portland travel itinerary, cross the Willamette River to the east side of Portland to explore some of the best districts.

Buckman District

Delve into the Buckman Neighborhood, a foodie haven and craft beer paradise that you shouldn’t miss on your Portland Weekend itinerary.

If you need a late afternoon pick-me-up, stop at Rimsky’s – an eclectic (and some say haunted) cash-only coffeeshop located in an old Victorian style house. Next, if you want to stay on theme, take a walk through nearby Lone Fir Cemetery, an enchanting final resting place for many of Portland’s most prominent citizens.

Hawthorne Street

Hawthorne is one of the coolest places to visit in Portland, Oregon. True to the spirit of the city, there street is home to an array of hip shops, independent retailers and eclectic eats.

Pro Tip : Travelers who want to spend the entire day in East Portland can skip downtown sightseeing and start with brunch at Jam on Hawthorne, one of the best places to eat breakfast in Portland. Then, with a full belly, begin a full day of shopping along Hawthorne!

Hawthorne Street Vintage Shopping

Visitors can dig for vintage threads at House of Vintage, Village Merchants, Magpie or Red Light Clothing Exchange.

For more nostalgic shopping, stop by the local family-run Excalibur Comics – or search for vinyl at Jackpot Records and Tomorrow Records.

Mount Tabor

The east side of Hawthorne ends at Mount Tabor. The little park was once a volcano, but now provides incredible views. Take one of the numerous paths that weave through the forest and around the reservoir to get to the top of Mt Tabor.

An Evening Out on Day 2 of Your Portland Weekend Trip

The city’s east side districts are a fun and vibrant place to delve into a night of food, drinks and entertainment.

Spend an Evening in Buckman

If you want to eat dinner in Buckman, stay on Hawthorne Street – which, in addition to being lined with vintage stores and boasting heaps of character, also hosts numerous restaurants. The eateries range from fine dining to farm fresh to funky fare.

That said, our favorite spot for a meal in Buckman is the Cartopia food cart pod. Located on the northwest corner of the Ladd’s Addition neighborhood (one of the oldest planned neighborhoods in Portland), the Cartopia food cart pod offers a variety of delicious fare. We recommend getting a bite to eat from multiple vendors for a complete Portland foodie experience.

Still hungry? No shame! Venture around the corner to Asylum Food Carts and get a savory Dutch-themed waffle sandwich from Smaaken.

Another popular dining establishment on Hawthorne – that is not a food truck – is Por Que No – a popular Mexican eatery serving unbelievably good tacos and refreshing margaritas. (Numerous Portland locations if you’re full!).

Buckman Brewery Hop or Patio Cocktails

After dinner, sample more Portland craft beer as you bar hop from brewery to tap room in Buckman. Cascade Brewing Barrel House, Grand Fir Brewing, Lucky Labrador Brew Pub and Away Days Brewing Company are a few of the favorite Buckman brewery tap rooms.

Alternatively, sip cocktails at Rontoms – a laid-back restaurant with live music and good food. Plus, they have a patio with picnic tables and ping pong.

The Goodfoot – with a basement live music venue and an upstairs pub – is a fun place for nightlife in Buckman.

Dinner and Drinks in Division

On the other hand, you could leave Buckman and go a bit further south to Division, where you can feast on famous burgers at PDX Sliders – which many say is a Portland, Oregon Itinerary must-do!

Then, attend the Saturday midnight showing of The Rocky Horror Picture Show at Clinton Street Theater.

Top Tip : Pok Pok – and specifically their fish sauce wings – were long a staple on Division Street, but they have sadly closed their doors.

A Night on North Mississippi Avenue or in Alberta Arts District

Shops, restaurants, bars and theaters line the festive five-block stretch of North Mississippi Avenue in the historic North Portland neighborhood of Humboldt.

Nearby, the Alberta Arts District is another area in Portland, OR that is bustling with restaurants, bars and culture. Go underground to Les Caves Wine Bar, drink a divine Bloody Mary in a converted gas station at Radio Room or sip local craft beer at Great Notion Brewing.

More Evening Portland Entertainment Options

Eating and drinking isn’t the only way to spend a night out in Portland. The city is well-known for it’s district movie theaters that show Indie films – plus there are heaps of stages where visitors can catch a major production or independent play. Plus, Portland is home to numerous professional sports teams.

McMenamins Bagdad Theater and Pub is a renovated 1927 movie theater and the Hawthorne Theater is a fun performance venue with a wide variety of acts.

Sports enthusiasts can catch a game when visiting Portland. The NBA Portland Trail Blazers play at Moda Center, just across the Willamette River from downtown or you could join the ‘Army’ of Portland Timbers fans for a MLS soccer match at Providence Park. Numerous other teams (like the collegiate baseball Portland Pickles and the junior ice hockey Portland Winterhawks) play at various times throughout the year.

Day 3 of Your Portland Weekend Itinerary

On Day 3 of your weekend in Portland, Oregon you will see more of the best attractions. Spend time in the beautiful outdoors (or use our tips in the next section for rainy day museums), visit more cool districts and end the day at a renovated schoolhouse.

3-Day Portland Itinerary by JetSettingFools.com

Pine State Biscuits for Breakfast

Start the final day of your weekend in Portland at a local hot spot: Pine State Biscuits. The modern diner excels at hearty, home cooked meals that are downright good. Go for the rich and decadent Reggie Deluxe sandwich on a fresh made biscuit (but expect a long line to get it).

Outdoor Portland Activities

The nature surrounding the city is astounding! Lush and green, spending time at these outdoor spots is one of the top things to do in Portland in 3 days.

Washington Park, Portland Rose Garden and the Japanese Garden

A city park since the 1870s, Washington Park is a 410-acre park featuring several attractions – and visiting is a must on your Portland, Oregon itinerary!

In addition to the 15 miles of hillside, forested trails, the top park attractions include the Oregon Zoo, Hoyt Arboretum, the International Rose Test Garden and the exceptional Portland Japanese Garden. The Redwood Observation Deck, memorials, statues, museums and playgrounds are more Washington Park highlights.

Forest Park

West of Washington Park, visitors can hit the trails in the even larger Forest Park. The urban hillside park overlooks the Willamette River and features 70 miles of trails. Enthusiastic trekkers can make a detour to walk across the historic St. Johns Bridge.

Rather than tackling the trails on your own, visitors can join a local guide for a hike on the best trails to the best sights – including the International Rose Test Garden, the Japanese Garden and the Witch’s Castle. Get more details!

Discover NW 23rd

After trekking through the parks, if you want to spend the entire day in the area, aim for NW 23rd Avenue. Wander through the quaint Northwest District and eat lunch at a hip local restaurant – or dine at the charming Nob Hill Food Carts.

Afterwards, go to the interactive and incredibly entertaining museum, The Freakybutture Peculiarium and Museum, which is a fantastic place for funny photo ops and getting a little weird in Portland!

Walk along NW 23rd popping into boutique shops and galleries – and then cool down with ice cream from Salt and Straw, an artisan Portland-based ice creamery featuring unique flavor combinations.

Willamette River Boat Rides

Alternatively, get out on the river! A tributary of the Columbia River, the Willamette River flows right through the heart of Portland and is fun for outdoor recreation. One of the top Portland vacation ideas for river activities is taking a Willamette Jet Boat ride.

There are different jet boat tours to choose from – like Willamette Falls, the Shipyards or a quick scenic sprint along the waterfront and under bridges. The rides – which are absolutely thrilling – guarantee that passengers will get wet, so be prepared for that!

An alternate option is to travel by jet boat on a 3.5 hour trip under Portland bridges and up the Columbia River to see Multnomah Falls. Book it here!

If a soppy speedboat ride isn’t your style, opt instead for a relaxing Lunch Sightseeing Cruise for your Portland weekend itinerary.

East Portland Outdoor Parks

If you still have room in your Portland vacation itinerary (or if this is not your first trip to Portland) and you are looking for unique outdoor adventures, consider a couple of the best east side parks – including an extinct volcanic cinder cone and an interesting grotto.

The Rocky Butte Natural Area on Portland’s east side is an excellent neighborhood park. The extinct volcano features a gorgeous lookout point that is definitely worth including in your 3 Days in Portland Itinerary. If you get a clear day, the elevated Rocky Butte Park peak offers stellar views of Mount Hood.

Nearby, The Grotto is another fantastic place to see in Portland, OR. The National Sanctuary of Our Sorrowful Mother is an outdoor shrine that dates to 1924. Today, visitors come to celebrate mass, walk the beautiful gardens and revel in the Christmas Festival of Lights (during the month of December).

McMenamins Kennedy School

Spend the last few hours of your Portland 3 Day Itinerary at the McMenamins Kennedy School. Don’t worry – you won’t be sitting in a boring classroom. Instead, you will be sipping cocktails or soaking in a saltwater pool (just be sure to make advance reservations for a swim!).

Headquartered in Portland, McMenamins is an Oregon brand that is known for renovating historic buildings and transforming them into truly spectacular venues of entertainment – and Kennedy School is one of the best. In addition to the multiple bars and pool, the property is also a hotel. (We talk more about places to stay in Portland below.)

Visitors with a car might want to travel further afield to the McMenamins Edgefield property. Located in Troutdale (which marks the beginning of the historic driving route to the Columbia Gorge Waterfalls ), Edgefield is a 74-acre entertainment hub, inclusive of a hotel, winery, distillery, brewery, restaurants, pool, theater, golf and gardens (oh, my!).

More Things To Do in Portland, Oregon in 3 Days

We have highlighted the best things to do for your Portland Itinerary 3 Days trip – but we have a few more suggestions.

In the event of wet weather, check out some of the museums in Portland. Or, if you want to see more of the region, embark on one of the day trips around Portland, Oregon.

Indoor Activities: Portland Museums

If foul weather keeps you from being outdoors during your weekend in Portland, don’t despair! There are plenty of cool places to see in Portland that are indoors. In fact, we already mentioned spending time at The Freakybutture Peculiarium and Museum – but there are many fascinating Portland museums.

We are featuring just a few of the top museums to include on your 3 Day Portland Itinerary.

The Oregon Museum of Science and Industry is one of the best museums in Portland, OR. Featuring interactive and engaging science-based displays, the museum is family friendly (but appeals to visitors of all ages!).

The Pittock Mansion

Located just north of Washington Park, Pittock Mansion was built in 1914. Today, visitors can see the 23 rooms in the mansion that are decorated in period pieces. Plus, the garden has a phenomenal viewpoint (which can be visited without paying entry into the mansion).

The Oregon Historical Museum

The Oregon Historical Society Museum delves into the history of the land and people – tracing it from pre-historic to modern times.

The Portland Art Museum

Displaying a fine collection of artwork from around the world, the Portland Art Museum has both a permanent collection and rotating exhibits.

Portland Views from Above

Throughout our Portland Three Day Itinerary, we featured some of the best viewpoints in the city – but there are two more we want to highlight.

OHSU Skyline Viewpoint and Gondola

On a clear day, there may be no better view than from the OHSU viewpoint. That said, getting there via gondola is half the fun!

Transporting passengers from the South Waterfront to the hillside Oregon Health and Science University hospital campus, the aerial tram takes just 4 minutes to ascend to the viewpoint.

For a group experience, join a guide for sunrise from the viewpoint – along with craft coffee and donuts. Get the details!

Portland Airplane Tour

What better way to see Portland sights than from above?! Visitors can take a short, scenic plane ride to view Portland from an incredible vantage point. Book it here!

Portland Day Trip Options

Columbia River Gorge Waterfall Trip Itinerary

During your weekend trip to Portland, taking a day trip is a perfect way to see more of the stunning surrounding region. Top day trips from Portland to add to a weekend in Portland are the Columbia River Gorge Waterfalls, wineries and the Oregon Coast. We are featuring a few of the highly-touted Portland tours.

Morning Multnomah Falls and Columbia River Gorge Waterfall Tour

If you have a rental car , use our detailed Guide To The Columbia River Gorge . We share the absolute best way to see the waterfalls on a Portland road trip.

If you want to leave the driving to someone else, consider a highly rated half-day tour that features the area’s beautiful waterfalls along the scenic byway. A guide offers interesting information about Oregon, while participants get to take in the breathtaking vistas. Book your spot!

Either way, the gorge is a perfect destination to include on a Portland weekend trip.

Columbia River Gorge Adventure by Bicycle

When visiting Portland in a weekend, there is plenty of time to discover the outstanding beauty of the Columbia River Gorge on bicycle. The tour guide leads participants on an easy bike ride, making stops along the way to hike to nearby waterfalls. Guests can choose from morning or afternoon day trips from Portland. Find out more!

Willamette Valley Wine Tasting Tour

On your Portland trip, spend the afternoon visiting 3 incredible wineries in the picturesque Willamette Valley. The small-group tour features travel by minivan (and pick up/drop off at downtown hotels) and wine tastings at all 3 stops. Get more details!

Oregon Coast Tour From Portland

The Pacific Coastline in Oregon is a magnificent sight! We actually recommend taking a few days to complete a coastal drive – which you can read about in our complete guide to an Oregon Coastal Drive !

However, visitors short on time can still get a glimpse of the coast on a full-day tour. This Portland day trip itinerary includes the incredible scenery from Cannon Beach, Ecola State Park and Oswald West State Park. Learn more here!

Vancouver, Washington

Just north of Portland across the Columbia River is the city of Vancouver, WA – and it’s a fabulous place to explore during your 3 Day Weekend in Portland. The city – which feels more like a small town and is often referred to as a suburb of PDX – offers a fantastic waterfront, a handful of interesting sights and a buzzing craft beer scene . Use our tips for Things To Do in Vancouver, WA to plan your day trip from Portland.

Crater Lake National Park

Many visitors are tempted to squeeze in a road trip to Crater Lake into a weekend Portland itinerary – but, honestly, we think the 4-hour drive each way is too long during your short weekend trip. That said, if you are planning a longer trip to Oregon and need additional Portland vacation ideas, Crater Lake can be a fabulous option. We share many more tips for a longer vacation to Portland in the next section!

More Portland Itineraries

Many people planning a trip to Portland wonder, “ How many days in Portland, Oregon is enough? ” While we think three days in Portland, Oregon is an ideal amount of time to see the sights, we could easily spend weeks exploring the city and region. However, what ultimately determines how long to plan a Portland vacation itinerary is interests, money and overall allotted time-frame.

Perhaps your time is limited to just a 2-Day Itinerary for Portland – or maybe you are planning a week-long Oregon vacation itinerary. To help in the planning process, we are sharing our top suggestions for alternative itineraries.

Portland Itinerary 1 Day

Whether you are taking a day trip to Portland or are planning to see Portland in one day as part of a larger PNW itinerary, there are numerous ways to spend your time. For us, a perfect Portland 1-Day Itinerary would include top sights, the best districts and iconic food.

To make the absolute most of a day in Portland, we recommend starting with a half-day tour by vehicle that takes in the top sights. Then, in the afternoon of your Portland 1 Day Itinerary, pick one district (or park) that is most appealing to you – and go discover it on foot. Depending on which neighborhood you choose, you could stop for a Voodoo Doughnut or Salt and Straw ice cream, then pop into a few craft breweries to get a good taste of what Portland has on offer!

2-Day Portland Itinerary

With 2 days in Portland there is just enough time to see the highlights. In order to create the best Portland 2-Day Itinerary, we recommend using parts of our above outlined 3 Day Portland Itinerary. However, for the best flowing Portland Itinerary 2 Days, on your first day, we recommend following our tips for Day 2. Then, on the second day, spend the morning at a park or on the Multnomah Falls tour; spend the afternoon in the Pearl District exploring the sights and sounds on foot.

Alternate Portland Itinerary 3 Days

While we think our outline for a 3-Day Itinerary in Portland, Oregon is the best way to see the city, it is certainly not the only way! Visitors who want to spend more time in nature can easily cut out some of the city sightseeing in favor of urban parks and the waterfalls tour .

And, vice versa, travelers most interested in city attractions can eliminate some of the outdoor adventures and spend more time in the districts and neighborhoods – like the Alberta Arts District or Mississippi/Williams.

4-Day Portland Itinerary

With 4 days in Portland, visitors have enough time to see the top attractions and go on a day trip from Portland. To create the best Portland Itinerary 4 Days, we recommend following our outlined plan for 3 days in Portland, then, on the last day, go on a full day tour.

Portland 5-Day Itinerary

Creating a 5 days itinerary in Portland, Oregon allows ample time for sightseeing, active adventures and a day trip. With 5 days in Portland, we recommend following the 4-Day Itinerary for Portland, Oregon (directly above), then spend the last day exploring another neighborhood or hop over the Columbia River and visit Vancouver, WA !

Oregon Itinerary One Week

As we already mentioned, we would have no problem planning a Portland travel itinerary for several weeks. That said, we think the best way to plan a Portland 7-Day Itinerary is to divide your time between the city and the coast.

7-Day Portland Trip Ideas: City and Coast

To create the best Portland and Oregon Coast Itinerary, you can use our day-by-day 3-Day Portland Itinerary – and then add on our Oregon Coastal Drive Itinerary . Our coastal drive trip plan features four days driving down the coast, visiting cute coastal towns (like Florence, OR ) and hiking some amazing Oregon trails .

7-Day Portland Trip + Bend and Crater Lake

Visitors who have already been to the Coast of Oregon could create a Portland to Crater Lake Itinerary. After 3 days in Portland, take a 4-day round-trip adventure to Crater Lake. If time permits, we recommend a visit to Bend, Oregon on the way back to Portland.

Visit Portland or Seattle?

Many people debate whether to visit Seattle or Portland – and, we admit, it’s a tough call! Because of their proximity, we actually suggest visiting both by creating a Seattle and Portland Itinerary.

To make the most of a Seattle-Portland Itinerary, we think you should plan at least five days (but a week would certainly be better and might give you time to check out hip Spokane ).

Top Tip: To plan a Seattle and Portland vacation, you can use the tips from our Seattle Itinerary !

Portland Oregon Map

Use this link to Google Maps to find your way to all the best things to do in Portland, Oregon.

Portland Itinerary Map by JetSettingFools.com

Travel Tips For Your Portland Itinerary

Now that you know what to do in Portland in a weekend, we have a few more tips for your trip.

Organizing Your Portland 3 Day Trip

We have shared detailed information about how to plan a trip to Portland, Oregon.

As you make your trip plans and reservations, we recommend using a travel planner to keep track of the details. Our Trip Planning Printables are perfect for making sure nothing falls through the cracks!

Travel Planner Printables by JetSettingFools.com

Portland Food and Drink

Throughout our Best Weekend in Portland Itinerary we highlighted top restaurants and hip bars. The eateries that we shared are some of the most popular places to eat in Portland, OR – so we highly recommend making reservations in advance, if possible.

When Is The Best Time to Visit Portland, Oregon?

We think the best time to visit Portland, Oregon is summertime to early autumn; specifically, from June until early October. Summers in Portland tend to be dry and sunny – which is perfect for outdoor activities (and the rose gardens).

The mild temperatures is what makes summer the best time to travel to Portland. However, the high humidity can be stifling and it’s also the height of wildfire season.

Late autumn through spring can be rainy, which could seriously put a damper on hikes and even neighborhood exploration. That said, with an umbrella, raincoat and some patience, it can be a fine time of year to visit Portland. In fact, for visitors from the Northeast or Midwest, the milder weather makes Portland a great US winter destination .

How To Get To Portland, Oregon

Portland can be reached by plane, train, bus or car. On our most recent Portland trip we flew from Columbus, OH and departed to Montana . When we need to buy plane tickets, we start our search for the best airfare on SkyScanner – but first be sure to read our detailed Tips for Booking Flights .

The Portland International Airport – PDX – is the main airport in Oregon. PDX is well-connected via public transport, but private ground transportation is also available and should be booked in advance .

Do You Need A Car in Portland, Oregon?

For our Weekend in Portland Itinerary, it is not necessary to rent a car . The city has an exceptional network of public transportation – including the TriMet Bus and MAX Light Rail systems. Uber is also available as well as Lyft. It is easy to get around Portland on foot, scooter and by bicycle as well.

Additionally, visitors can get to the top Portland attractions on the Hop On Hop Off Pink Trolley Bus. In addition to making stops at all the best sights in Portland, the trolley also provides live on-board commentary and an open-air seating area for the best views. They offer 1- and 2- day passes. Get tickets here!

Where To Stay in Portland, Oregon

We think the best place to stay in Portland is central to all the best Portland, Oregon sights to see. That said, travelers with a car might prefer staying beyond downtown in one of the unique McMenamins hotels.

The Paramount Hotel

We have stayed in various hotels on our trips to Portland – and can personally recommend staying at The Paramount Hotel. Located right in the heart of downtown, The Paramount Hotel offers clean rooms, comfy beds, an on-site restaurant, and sincere staff – all at an affordable price! Check rates and availability!

The Benson Hotel

We have yet to stay at the historic Benson Hotel, but it is an iconic, luxury hotel in the Portland city center. Top features are the elegant rooms and top-notch service. Bonus amenities are the gym, laundry facilities and business center. Check rates for your stay!

We highlighted the McMenamins Kennedy Schoolhouse as one of the fun places to spend an evening imbibing and swimming, but it is also one of the best places to to stay in Portland! Located near the Alberta Arts District, travelers can use public transit and Uber to get to Downtown Portland sights and other districts.

In addition to the multiple bars and heated swimming pool, the property also has an on-site movie theater. Each room is uniquely designed – some are even on old classrooms – and they all have ensuite bathrooms. The hotel does sell-out often, so book it in advance !

Other fun McMenamins hotels in Portland are the McMenamins Crystal Hotel in Downtown PDX ( check rates! ) and the McMenamins Edgefield Portland Hotel outside of the city center ( check availability! ).

Choosing where to stay in Portland for a weekend? Find the top hotels and great rates on Booking.com – and use our Top Tips for Booking Hotels to ensure you get the best value!

Portland Vacation Rental

Like many big cities, there are several holiday apartments that visitors can rent for their weekend stay. That said, for your 3 Day Portland Itinerary, we recommend staying in a hotel, rather than an Airbnb apartment.

We usually love staying in Airbnb accommodations – they tend to be less expensive and feature a kitchen for preparing simple meals. However, for a short weekend trip to Portland, Airbnb fees can be excessive and with all the fabulous Portland food, you likely won’t be dining at your accommodations!

What To Pack For Your Portland Trip

We have a few final tips for your Portland vacation! Get our top Packing Hacks and more on our Ultimate Packing List . Need a Packing Checklist? Get your FREE Packing Checklist here !

Walking Shoes for Portland

We cover a lot of ground in our Portland 3-Day Itinerary! We recommend wearing a pair of comfortable walking shoes during your exploration. I like to wear these Columbia shoes for women and Kris likes Merrell trail shoes. Both of these shoes are good for most of the nearby Portland hikes, too!

Portland Weather Appropriate Clothing

While summer days in Portland can be hot, nights can be cool. We recommend packing clothing for your trip that can be layered – and even in the summertime, you will likely want at least a lightweight jacket. Extra layers are also essential if going on a jetboat tour or into the Oregon mountains. Remember to bring a wide brimmed hat , good sunscreen and insect repellent , too.

In the non-summer months, it is ideal to have a packable raincoat and a travel umbrella , too!

Portland, Oregon Travel Guide

In our Portland weekend trip itinerary, we have outlined the best things to do in Portland, Oregon. However, it is always a good idea to have a travel guidebook – like this one – for even more information and to take notes!

Travel Camera for Oregon Photography

Portland is an incredibly photogenic city! Rather than capturing the sights with your phone, we recommend upgrading to an actual travel camera . We use a Canon Rebel with an everyday 18-135mm lens . This camera comes bundled with all kinds of fun accessories, making it a perfect budget camera for budding photographers!

Binoculars

If you do plan on taking day trips from Portland into the nearby nature, we highly recommend bringing binoculars with you.

Day Bag for your Portland Trip

Whether you travel with a backpack or a suitcase , for your long days of Portland sightseeing you will also want a great day pack to organize and secure all of your everyday travel items !

Oregon Travel Guides

Oregon ranks as one of our favorite places to visit in the United States – and we have heaps of tips for fellow traveler! Use our travel guides to help plan your perfect trip to Oregon.

Driving to Columbia River Gorge Waterfalls
How To Plan a Oregon Coast Road Trip
Things To Do in Florence, Oregon (including the best Central Oregon Coast Hikes !)
What To Do in Bend, Oregon
All the Best Oregon Things To Do

Start planning your US Trip ! Search for the lowest airfares , the best accommodations and fun things to do …then start packing ! Want more travel planning tips? Head over to our Travel Planning Page for more information and tips on traveling – and for country-specific information, take a look at our Travel Guides Page !

We Want To Know: Is there anything you would add to our Portland Itinerary? What is your favorite way to spend a Weekend in Portland? Give us your best tips and advice in the comments below!

Visiting Other Top Destinations in The USA?

We have been fortunate to travel to some of the Best Weekend Destinations in the country – and check out our top Underrated Places to Visit as well!

You can also take a peek at our detailed guides for Indy , Pittsburgh , Cincinnati , Denver , and Chicago . How about a weekend in New Orleans , Nashville , Phoenix , Boston , Austin , or San Diego ?

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Portland Itinerary A Weekend in Portland, Oregon by JetSettingFools.com

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PORTLAND’S ONLY UNDERGROUND DOUGHNUT TOUR

Insider’s tip: decadent dining in downtown portland.

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Experience portland’s street art by bike, embark on a day trip to the oregon coast, insider’s tip: dinner at andina restaurant, delve into the heart of oregon’s wine country, insider’s tip: dine like a local at kachka, insider’s tip: start your day at the screen door restaurant, insider’s tip: explore division neighborhood, accommodation options.

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Hotels to Book for a Trip to Portland

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How to Spend 5 Perfect Days in Portland, Oregon

As a city traveler, Portland has been on my US bucket list for a long time. It has so many things that appeal to me about cities—excellent restaurants, strong pedestrian culture, adorable boutiques—making it the perfect urban getaway! I knew spending only a few days in Portland wouldn’t be enough to see all the amazing things that the city has to offer, so I decided to spend a 5 full days exploring. This allowed me to visit several different neighborhoods and I even got to take a few day trips outside of the city to enjoy the nearby mountain and coastal scenery.

From the artsy northeast neighborhood of Alberta to the unique Japanese gardens in the southwest area, there is something in Portland for everyone to enjoy. Portland has to a lot offer, and its proximity to both the coast and the mountains makes it an amazing destination all year round. The summer is the best time to go but the fall and spring are always beautiful.

Day One: Rose Garden and Downtown

For your first day in Portland, you’ll be exploring some the famous "must-see" spots in Portland, Oregon including Japanese Gardens, Powell’s Bookstore, Voodoo Donut and the International Rose Test Garden.

West of downtown Portland is where you’ll find the International Rose Test Garden . This is where botanists and scientists test out new hybrids of roses which includes breeding different roses together or breeding roses with other species. Situated on small, easily walkable terraces, the Rose Garden is simply beautiful. Brick lined sidewalks meander through rows of flowers, all of which bloom at different times during the year so you'll always have a chance to smell the flowers. There are so many unique varieties and colors to explore and my favorite were the magnolia and rose hybrids because they smelled amazing!

If you've already made the trek out to the Rose Garden, I definitely recommend stopping at the Japanese Garden as well. With nearly 6 acres to walk, there are several different paths you can take around the park to see all five main gardens. The different gardens are styled in traditional Japanese landscape architectural designs. Of the 5 gardens, there is a tea garden as well as a zen sand and stone garden, which I really enjoyed. It's a relaxing and tranquil place to wander around. On a clear day, you can even see Mt Hood in the distance!

International Rose Test Garden Portland Oregon

Once you’re done taking in the garden vibes, head back into the city center for the rest of your morning. Voodoo Donut , a famous bakery and donut shop in downtown Portland, is known for its wacky donut flavors. The bright pink walls and kooky dressed cashiers dancing to punk rock really completed the atmosphere. There is small patio next to the restaurant for patrons to sit and enjoy the donuts and of course, people watch. If you want a full write up about Voodoo Donut, check out my post comparing them to other Portland donut tycoon Blue Star.

Known as a city of books, Powell's Bookstore is a four story book store that literally covers an entire city block! There is endless opportunities for discovery so you should grab a map when you walk in so that you can navigate where you're going. It is easy to spend hours in here wandered the towering shelves of books looking at different sections as the smell of books, old and new, fills your senses and brings the store to life. There are lots of nooks with vintage couches to enjoy a few pages of your newest purchase, or relax as you decide which section to visit next!

Day Two: Day Trip to Oregon Coast

Needing a break from the hustle of Portland, the Oregon coast is only an hour drive from Portland, making it the perfect day trip from the city. Start with a visit to Haystack Rock in Cannon Beach. Just offshore from a wide expanse of beach, Haystack Rock is a famous freestanding rock that stands solitary in the ocean with waves crashing around it.

We were there during high tide, otherwise we might have been able to walk out to it. But it made for a perfect spot to enjoy a beer and relax as you people watch people coming to take selfies and Instagram shots of the famous backdrop.

Continue your drive along the coast to Devil's Punchbowl (or Devil’s Cauldron depending on who you ask). The pounding ocean waves have eroded to create an open roofed cave and amazing gorges along the coast. It was a beautiful spot and we managed to make it there while it was bright and sunny. The roaring sounds of the waves and the bright pops of color from the rock and shrubs made for a lovely view.

You’re probably hungry for lunch at this point and Tillamook Creamery is the perfect place to stop. I don’t know about you, but I realllllllly love cheese. Tillamook Creamery is a famous Oregon cheese-maker with years of experience in all sorts of dairy-related endeavors. At their flagship location, you can eat delicious local cuisine while watching cheese making in process. Don’t forget to save room for a delicious scoop of some of the creamiest ice cream ever! Their massive gift shop has all kinds of unique cheese-inspired gifts to bring home to friends.

Before heading back to Portland, stop by one of the Pacific Northwest’s famous local breweries. There are lots of them scattered along the coast, so there are plenty of options. We opted to try out Rogue Brewing because it is one of our favorite breweries. Their original location is located in Newport where you can get both a brewery tour and sample the full menu in their taproom!

Day Three: Northeast Portland

Portland has a lot of distinct neighborhoods, each with their own flair, shopping scene and food style offering a unique set of experiences in the different districts. For your third day in Portland, you’ll explore the northeast neighborhoods of the city—Alberta and Boise.

Starting with the Alberta district neighborhood is a quirky artist area with lots of cute shops and delicious restaurants. While this travel itinerary will include specific suggestions to explore while in Northeast Portland, the Alberta neighborhood is one of those perfect areas for just wandering around and discovering your own hidden gems!

Did you know that there is no sales tax in Portland ? Naturally that means you should shop your heart out! Here are some of my favorite shops that I visited in the Northeast while traveling for 5 days in Portland:

Best Place for Succulents : Digs . A great garden & home décor store, Digs has an awesome selection of cool succulents, including air plants! Plus, they’ll serve you up a free cup of espresso as you walk around.
Best Place for Art & Craft Supplies : Collage . A two store front place, there are so many supplies in here from painting to scrapbooking. It’s fun to wander around and see all the vintage trinkets they’ve collected, like loose scrabble tiles and stray address numbers.
Best Place to Find a Gift for Your Boyfriend : Cord . When I walked in here, I immediately thought of how much Sam would love this place. Cool outdoorsmen books, neat gadgets for camping and a case full of knives all displayed in a modern and easy to view way.
Best Place to Find Cute Handmade Dresses : Amelia . This place has a ton of gamine style clothing handmade in Portland and the nearby areas. It’s cute and girly and their jewelry selection is surprisingly quirky! (cover photo of this post is from there)
Best Place for Funky Vintage Selection : Bristlecone Vintage . Just off of Alberta Street, Bristlecone is a hole in the wall place with a well-curated selection of vintage Pacific Northwest style pieces. Think fleece jackets, high-waisted denim and plaid.

The next neighborhood of northeast Portland that you’ll explore on your third day in Portland, Oregon is Boise . The main street in this area of Portland is Mississippi Avenue where you’ll find a dense cluster of shops and restaurants. Similar to Alberta, it is fun to just walk around this area and discover spots on your own. Need restaurant recommendations for the northeast part of Portland? My foodie travel guide will have you eating some of the best spots that this neighborhood has to offer!

A few of my favorite Mississippi Avenue shops are:

Best Place to Find Quirky Art Prints & Cards: Land . Stocked full with handmade, local prints, Land is open early for browsing while waiting for brunch. They’ve got a quirky and eclectic style with lots of cards and wall prints, as well as screen printed Oregon themed tees.
Best Place for Cool Camping Gear: Worn Path . A great store for your outdoorsy brother or boyfriend, Worn Path offers a log cabin-esque vibe filled with classic but stylish camping accessories and supplies.
Best Place for Western Style Clothing and Backpacks: Animal Traffic . With a great selection of Hershel Supply Co. backpacks and second-hand flannel, Animal Traffic has a distinctly western-meets-northwest vibe. I went here hoping to find a vintage Pendleton jacket, and walked out with an awesome vintage poncho.

Day Four: Day Trip to Multnomah Falls

A short half hour drive outside of Portland will put you in the Columbia River Gorge . The canyon is extensive, and there is lots of hiking all around the area, both on the Oregon and Washington sides of the gorge. Since I only had a few days in the Portland area, I didn't want to do any extensive hiking but just off the highway is a beautiful waterfall visited by thousands of people every year—Multnomah Falls.

Multnomah Falls Scenic Area is another perfect day trip from Portland, Oregon. You can see the falls from the parking lot, but if you walk up the short paved path, you'll get a much more impressive full view of the falls. Multnomah has an upper and lower falls with a bridge that crosses over the two. The upper falls are much longer, nearly 550 feet, while the lower falls are about 70 feet, making this the tallest waterfall in Oregon.

It's really easy to walk right up to the falls and the bridge. The path is full paved and isn't strenuous, so it's great place for a family outing. There are lots of tourists there, so expect a bit of a crowd. Surrounding the paths are Oregon's beautiful mossy forest and trees, so it's quite beautiful.

Once up to the bridge, you can continue on for a little bit longer walk. I continued up the trail which leads to top of the upper falls. There are 11 switchbacks, and it takes about 45 minutes to walk up. The overlook itself isn't impressive because you can't really see the falls well. I did, however, enjoy a nice view of the Columbia river and gorge. Although it was only a short uphill walk, it was nice to get outside on a beautiful afternoon day and spend some time in nature.

Day Five: Southeast Portland

For your final day traveling in Portland Oregon, you’ll take another neighborhood tour but this time of southeast Portland! There are two key neighborhood areas to explore in southeast Portland — Hawthrone and Richmond. The Hawthorne neighborhood , one of the most historic areas of Portland, has lots of scenery to enjoy with their many beautiful Victorian homes. The main street, Hawthorne Street, gives the neighborhood its namesake but it also has a fun, friendly vibe that contributes a lot to how people typically think of Portland.

Similar to northeast Portland, this is a great area to just wander around and discover hidden gems of your own! There are plenty of cool shops in the Hawthrone neighborhood where you can spend a few bucks. My favorites were:

Best Place for Friendly & Helpful Staff : Imelda’s Shoes . When I was in Portland on my last trip in 2012, I spent like $400 here on amazing quality leather shoes that I still have and wear today! The staff is really friendly and helpful, and they know their brands so you aren’t stuck wandering the piles to find the best for you.
Best Place to Find Affordable Thrift Style: Crossroads Trading . Gotta give a shout out to my favorite second-hand clothing store! I frequent this shop in Chicago, so I definitely knew I wanted to check out the one in Portland. They’ve got lots of great stuff for a fraction of the price.
Best Place for Reasonably Priced, Trendy Clothing : Sloan . There are three locations, but all serve up an awesome assortment of trendy clothing with a Pacific Northwest vibe at prices that are totally reasonable for what they are selling. I think the Mississippi location might be my favorite, but the one on Hawthrone is also great. I got an amazing plaid poncho here that I've been wearing non stop since I got home!

Only a few blocks south of the Hawthrone district you’ll find the more up-and-coming neighborhood of Richmond. The arrival of PokPok in this neighborhood triggered a flow of new businesses and restaurants opening up in this area as people flocked to the now-infamous Asian restaurant. You can see a lot of the buildings along Division street are new construction to accommodate the influx of new residents moving to this area.

There are plenty of other restaurants in Southeast Portland besides PokPok, so check out my food travel guide to discover my 15 favorite restaurants in Portland Oregon ! Since the Hawthrone neighborhood is still growing, I’m sure there are plenty of new spots to discover in the area but a few of my favorite shops that I found in the Richmond neighborhood are:

Best Place for an Head-to-Toe Outfit : Adorn . The sales associates at Adorn are friendly, and their easily pair-able separates and accessories make it simple to create a seamless outfit all in one spot.
Best Place for Best Place for Vintage Home Décor : Artifact . A mixture between vintage furniture store and on-trend consignment shop, Artifacts has a little bit of everything. I found an amazing thrifted maxi skirt as well as a vintage table runner. It’s just a fun place to walk around.

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Road is Calling

Weekend in Portland, Oregon – My Perfect 2 to 4 Days in Portland Itinerary

It took me almost two and a half years to write my version of the Portland itinerary. Not that I have been writing it for two years, no. But only two and half years after Mark and I left America I realized how much we enjoyed this city when restoring an old Victorian house there.

So I thought why not share all my favorite spots and points of interest in this very detailed post. No matter if you are coming for a few days during the week or for a weekend in Portland, all these places will have something to offer.

Portland, Oregon’s largest city, has many names. Some people call it the “city of roses” or “the city of bridges”. But, regardless of what you call it, you can be sure that you’ll find this city unforgettable, flourishing, and very green.

Portland attracts tourists from all over the world with its local microbreweries, cozy restaurants, brunch cafes, distilleries, and bookstores. In addition, it also has the indescribable beauty of the natural landscapes that are situated in close proximity.

Planning a perfect 2, 3, or 4 days (or weekend) in Portland itinerary can be a bit overwhelming since there are so many things to do and places to visit. So this post will answer all the questions and ensure that you get the most out of your trip.

Note: If you are visiting from out of state, want to go on a road trip from Portland and need a car, the best company to rent a vehicle is Discover Cars . They offer the best deals, provide good support and easy cancellations.

The Best Time of the Year to Visit Portland, Oregon

If you are wondering when to visit Portland, Oregon, you have to answer at first the question what’s the final goal of your trip.

Weather conditions in Portland facilitate a visit there at any season. The temperature is comfortable throughout the whole year.

Summers are not very hot, with the maximum average temperature of about +95F (35C) in August. But even then the difference between day and night temperatures is significant. Nights are usually cool and very comfortable. Also, it doesn’t rain a lot in the summer which creates comfortable conditions for various experiences. Additionally, this season is great since it’s full of festivals and various events.

Winters are moderately cold. In January, the average temperature is around 40F (4.5C) and it rarely drops below zero. Although the possibility of a strong snowstorm is not excluded. Winters generally see a lot of rainfall, although recent years (perhaps because of climate change) were drier and sunnier.

If you want to see Portland in all its green and blooming beauty, be sure to go on vacation in the spring. If looking for mind-blowing foliage colors then plan for the early fall. May-June and September-October are the best months to visit Portland weather vise. But winters are perfect for cozy cafes, breweries, and romantic getaways in charming Inns. The city of roses has so many of them.

How Many Days in Portland

Many people, when planning their trip to Portland, often overlook this West Coast city thinking that there is not much to do. We were like that too. We thought that spending a weekend in Portland would be enough. But then after just a few days there we figured that we could easily spend a week or even more.

So when thinking about how many days you should spend in Portland, decide at first on the activities. If traveling to this part of Oregon for nature or glamping , then one day in Portland may be enough. A city person would want to spend 3 or 4 days in Portland.

If you will be spending only 2 days, then make sure to prioritize what you’d like to see. My 2-day Portland itinerary is packed with the highlights of downtown and some green areas inside the city. However, it doesn’t include any sites outside Portland. Use ideas from the 3rd and 4th days to prioritize what you’d like to do.

Spending 3 days in Portland or more is ideal as it will allow you to cover not only the central part of the city but venture outside and visit wineries, breweries, spas, and waterfalls. Having time for a 4-day Portland itinerary is the best as it allows you to take it slower and experience everything in depth.

Getting To & Around Portland

Portland has its own international airport (which by the way is located right in the city and is easy to get to and from) with numerous direct connections with almost all US cities. This is why reaching Portland from any corner of the US and Canada is an easy thing to do. However, some travelers prefer to fly to Seattle, rent a car there, and drive to Portland.

If you are an international traveler, you may end up flying to Seattle too. There are many cheap flights between Seattle and cities in Europe and Asia, so going there is more convenient. Seattle international airport also has better rental car deals for those who plan to travel in Washington state before going to Portland. The two cities are also connected by train and getting from one city to another takes about 3 hours 30 minutes.

Once in Portland, you shouldn’t worry about the car. It is one of the most walkable cities in America with many protected bike lanes and walkable bridges that connect the city. Getting around Portland is easy and enjoyable also because of the efficient public transportation system. You can take a bus, a metro (Max Light Rail), or a Commuter Train (WES Commuter Rail) to get places.

When we volunteered in Portland, depending on where exactly we planned to go, we were taking buses, metro, or our car. We also walked a lot. But the easiest way to get around the city was definitely by bus and train.

If you follow my 2 and 4-day Portland itinerary and stay only in the city, there is no need to rent a car. But since Portland has so much natural beauty around, you may want to venture outside, especially if coming to Portland for 4 days or longer. And for that, having your own vehicle is a must.

Nearby Mount Hood national park, stunning Columbia River Gorge Highway , and even the Oregon coast with its cute small towns are pretty close. So you can easily combine a trip to Portland city with a road trip through the state.

2 Days in Portland Itinerary – Ideas For a Weekend or Any Time During the Week

If you have only 2 days in Portland and visit this city for the first time, the best way is to spend these two days in the city center. Explore the Pearl District, downtown, two neighborhoods in Northern Portland and famous green spaces in the western part of the city.

Day 1 of my itinerary concentrates more on cultural and historical experiences while day 2 brings you closer to nature.

And of course, both days are packed with quite a few awesome places where to eat and try some of the best famous drinks and cocktails.

Day 1 in Portland

Start your day at fuller’s coffee shop.

I assume that you are starting your day early and you are staying somewhere between Northwest and Pearl Districts. In this case, getting to an authentic diner with a feel of a small town will be easy and worth your effort.

Of course, if you are not having breakfast at your B&B or hotel, then get a classic diner experience in one of the best eateries in Portland. Fans of eggs, toasts, pancakes, waffles, hash browns, and never-ending coffee will have an old school American breakfast there.

Fuller’s coffee shop is really one of the most famous and popular places among locals with very delicious food and lively ambiance. Expect it to be busy, especially if planning a weekend trip there. On a weekday, there also may be a wait time to get a seat but you can always call ahead and make a reservation.

If you happen to crave bacon, this is seriously a place to go to. These guys know how to load you up on it.

Alternative places where to have breakfast : Mother’s Bistro & Bar is another classic breakfast and brunch spot in Portland with an amazing atmosphere and unique selection of menu items.

VISIT THE BEST BOOKSTORE IN THE US

Just two blocks away from Fuller’s coffee shop is Powell’s City of Books store – the biggest book store in the US with a rare section of unique books. I am not saying that you have to spend half a day here but why not to check this place out, especially if it’s on the way.

Powell’s books store is really huge. And it’s always so busy. The site has countless rooms with different genres and spread out computers that can help you find a book you need. A huge number of children’s books, new and used books of various genres mixed together provide an opportunity for anyone to choose the price and book they want.

Even if you don’t plan to buy a book, it is still worth the trip here just to see how huge space is and how many books are in one place. The massive book inventory and people visiting and working in the store make it a fun trip.

We spent good two hours on a thorough walk-through on all four floors, taking photos and looking around. Instagrammers, by the way, will really appreciate this place since there are a few spots around the store where you can take cool shots.

For a really quick visit, set aside at least an hour. But for someone who is interested in books, store’s cute little cafe, and a small gift shop with souvenirs from Portland, more time is definitely needed.

STROLL IN TOM MCCALL WATERFRONT PARK

Tom McCall waterfront park is always seeing various festivals and events. In the springtime, it also sees crowds of people who come to enjoy cherry blossoms in full bloom.

But in my opinion, it is a really nice park to visit at any time of the year. Don’t spend a lot of time but come for a walk or bike alongside the river, have a relaxing time and take good photos with the Hawthorne bridge in the background. The Waterfront park trail opens up a gorgeous view of the two bridges and the water. On a hot summer afternoon, it’s also a good place to splash around in the fountain and cool down in a breeze.

If you are visiting Portland for a weekend getaway, then come to Tom McCall park on Saturday morning. It has a nice Saturday farmer’s market with fresh produce.

On any other day, there is an opportunity to rent bikes, tandem bikes, and go on a boat cruise down the river. Some river cruises like this 2-hour lunch cruise through downtown Portland offer food, live music, and tons of positive emotions!

Oh, and on a day with clear skies, you can even see Mount Hood from there.

VISIT OREGON MARITIME MUSEUM

While visiting Tom McCall waterfront park, you may want to learn about the rich history of Portland’s founders and rivermen in this interactive museum. The Oregon Maritime Museum is housed on the historic steam sternwheeler Portland. It offers visitors to explore the last operating sternwheel steam tug in the United States.

The get the best experience, the museum offers interactive tours packed with many facts. During the tour, you can take a glimpse into the history of Oregon’s riverboat days. Very knowledgeable docents (who are volunteers there) will walk you through all the details about every aspect of the working steam-powered boat and show tons of models and artifacts.

Families who are visiting Portland with kids younger than 5 years old may want to skip the museum though. It will be difficult for children to appreciate maritime history and engineering technology.

The museum is open only on Wednesdays, Fridays, and Saturdays and the tour usually lasts a bit more than an hour. So if you really plan to visit, plan accordingly.

RENT A BIKE & EXPLORE PORTLAND CYCLING AROUND

Portland prides itself on being the most bike-friendly city in the US. Every year more new bike lanes and riding trails appear around the city and cycling on a bike here is a fantastic experience. When we were biking, it felt like we were in Europe, seriously.

So if you had to spend only a few hours in Portland and could pick only one experience, I’d definitely encourage you to go biking. Of course, if you enjoy this activity.

Besides Biketown PDX, a bicycle-sharing system, there are many privately owned bike rental shops around the city. You can literally rent a bike around almost every corner and follow famous routes in any direction .

Or for a more exciting experience, simply join a biking tour. Having someone show you all of Portland’s hidden gems and tell interesting stories can help you fit much more in one day. For example, check this 2-hour bike tour which covers all main city sights or a 3-hour full tour of downtown .

MAKE A QUICK STOP IN LAN SU CHINESE GARDEN

Lan Su Yuan garden is considered the most authentic Chinese garden in the world outside China. This tranquil oasis in the city center takes up the whole block and contains five elements of traditional Chinese gardens. Those elements are water, plants, rocks, architecture, and inscriptions. It’s very calming and fascinating to come here for a walk.

This garden is situated in a busy noisy neighborhood but once you are inside, it’s very relaxing and peaceful.

Pop in here to wind through the courtyards and pavilions. If budget allows, take a tour because guides do a great job describing all the nuances that go into planning a Chinese garden. There is also a beautiful tea garden on premises where you can rest and refuel with a lovely cup of tea and assorted light foods.

TAKE IN EPIC VIEWS FROM THE XPORT LOUNGE

In the end of the day, when you are done with sightseeing, why not sip champagne and enjoy oysters while taking in epic views of the city. Hey, another place with views of Portland, there are so many of them!

Xport Bar & Lounge, part of a very nice Porter Hotel , offers sweeping views along with the decor, vibe, and yummy snacks. Here, on the 16th floor, you can have a signature drink and a few bites while overlooking Portland’s skyline, bridges, and even mountains in the distance.

On a chilly night, choose to sit near the fire under the open sky. It feels so romantic!

Day 2 in Portland

On the second day in Portland, you should get acquainted with the city through its green areas. Washington Park and Macleay Park in the western part of the city are homes to gardens, sanctuaries, Portland Zoo, hiking trails, and some historic houses.

Also, any of these parks is just a really great place to go for a quick hike in Portland or a day out in nature. With its size and amount of activities, you can easily spend an entire day there. See below the points of interest not to miss.

And for the evening, pay a visit to famous Portland’s breweries or pubs.

VISIT THE JAPANESE GARDEN

Japanese garden in Portland rightfully deserves the title of a gem. Being different from the Chinese garden mentioned above, the Japanese garden also guarantees a spirit of tranquility and refuge from the busy city life. From the rose garden and ponds with fish to the hand-built waterfall, every part here is beautiful.

On our visit to Portland in the summer, our host recommended coming here the first thing in the morning to avoid crowds and have this garden to ourselves. And to be honest, it was a very smart decision. We really spent the first hour wandering on our own. This is why I am also recommending you to venture here in the early morning during the high season. In the off-season, any time of the day is good.

So, in this beautiful and serene place, you’ll find a blend of bushes, rare unique trees, beautifully made paths and sculptures, fountains, ponds, and pavilions. Five separate gardens offer a unique environment and design. A gorgeous coffee house is a great place for a quick snack. See the garden’s website for more details, pricing, and schedule.

SEE WORLD’S ROSES IN THE INTERNATIONAL ROSE TEST GARDEN

If visiting the City of Roses from May through August, make sure to include to Portland itinerary a visit to the well-maintained International Rose Test Garden. During this time of the year, the garden boasts thousands of roses and offers space for meditation.

In any other season, it is also a must-visit. Lovers of peaceful walks in nature in the middle of a city will appreciate some great views of the downtown skyline and Mt. Hood.

From Memorial Day through Labor Day, there are daily free tours led by trained volunteers that start at 1 p.m. Additionally, guided tours for a symbolic fee are also available throughout the year. Read more details about the tours as well as history and how to get there on the garden’s website .

From the downtown area or Pearl district, you can easily reach the International Rose Test Garden on foot, stopping for a meal at one of the cafes on the way there. Come here before (or for) the sunset when there are fewer crowds.

TOUR (OR WALK AROUND) THE PITTOCK MANSION

A beautifully restored mansion, which at the beginning of the 20th century belonged to a successful newspaper publisher Henry Pittock, today is a museum with interesting interiors, history, and art. Everyone who visits can go on a self-guided or group tour and transport 100 years in the past.

The house is built in heavy stone and has amazingly decorated rooms and interiors. Each room has a different design with many amazing details. Exploring the house will be very informative for both kids and adults alike. The mansion is really impressive and the hike through a forest park is a beautiful way to get there. If you are spending only two days in Portland and doubting either to go or not, you won’t regret this visit.

Even if you don’t feel like paying for inside access, it’s still worth taking a trip for the views alone. From the lookout point (which is a front yard of the mansion,) you can get a wonderful view of the city and Mt Hood in the distance.

Check more information about the tours, prices, and schedule on the Pittock Mansion’s website .

SEE A MUSEUM OF TREES IN HOYT ARBORETUM

Many cities around the US have their own arboretums. But honestly, none of them are as special as Hoyt Arboretum in Portland. You see, this place has 12 miles of trails that take you through a magnificent collection of rare trees.

Redwood, maple, magnolia and pine trees along with other types of trees and trails create various landscapes perfect for walking or jogging.

What’s interesting, Hoyt arboretum is listed in many magazines as one of the most beautiful urban parks in America. And a lot of people from all over the world come here just to see many unique trees in one living museum.

This park is great for all ages and is a good place to hide from the heat and hike around. On a cold winter day, it looks very spooky when covered in mist.

VISIT OREGON ZOO

If you’re an animal lover or traveling with kids, add to your Portland itinerary a lovely zoo situated in the nooks of the Portland ring forest. The zoo is not big but with all the exhibits you could definitely devote at least half a day to it.

The best part of the zoo is the first section with animals local to the Pacific Northwest only. It’s very interesting to visit for this part alone, skipping the rest which is pretty much the same as in many other American cities. With many exhibits and educational activities, the zoo has unique animals. Just some of those are pink pandas, painted dogs, rare types of bats, polar bears, and sea otters.

TAKE A WALK IN A MACLEAY PARK

Macleay Park is actually pretty popular among locals, that’s why it often gets crowded. But you understand why after taking a fairy tale walk through this corner of a bigger Forest Park.

The reasons to visit here are multiple trails for hiking, biking, walking, and horseback riding. There is an abandoned stone house to hike to and wildwood trail with a lovely river that follows the main path.

So if you love nature and feel like stretching your bones in a beautiful forest, don’t miss this place . Otherwise, you can return back to the city because there are still many cool Portland activities await you there.

GO ON A FOOD TOUR AROUND NORTHWEST DISTRICT

After you are done exploring the wooded area, head out to the opulent Northwest district. It is mainly famous for vintage shops, lovely family-owned stores with handmade produce, stylish cafes, and gourmet restaurants. Travelers who prefer to travel slowly can easily spend here an entire day, checking terrific eats and shops.

Here, as on a few other cool streets in Portland, you can go on a self-guided food tour, popping in almost any cafe or restaurant. All of the dining establishments have delicious food and a unique vibe.

Some of the most famous ones are:

– Elephants Delicatessen . A self serve establishment with incredibly delish and healthy options. Soups, sandwiches, cheeses, pastas, pizzas, a high assortment of salads, and many other foods are on sale here.

– The Dragonfly Coffee House . A cozy coffee shop with lots of books to read, plush armchairs to relax in, and many flavorful treats, lattes, and teas.

– Ken’s Artisan Bakery . The best bakery in town that sells always fresh bread, croissants, and pastries. Try one of their famous tarts or cinnamon roll.

– Salt & Straw Ice cream . A local ice cream chain with so many unique flavors to choose from! There are actually four stores with this ice cream around Portland. But if you happen to be in this neighborhood only, don’t miss this place.

If you are eager to get the most of your time, do a walking 3-hour long Northwest neighborhood food and drink tour .

4 Perfect Days in Portland Itinerary

Day 3 in portland .

If you have 3 or even 4 days in Portland, it’s a good time to explore the outskirts of the city since there are a few hidden gems not to miss! I offer you to discover the historic architecture, natural areas, cliffside catholic sanctuary, old hotel, famous Portland breweries, quirky eateries, and much, much more.

The third day though is packed with a lot of activities. You may need to push them to the following day.

START YOUR MORNING ON THE MISSISSIPPI AVENUE

On your third day in Portland, you can start a day with a trip to Mississippi Avenue. This one of the most popular streets in Portland started to get its trendy feel in the 90s. Back then it was somehow attracting modish souls who were buying condos and apartments and moving boutiques in. Today, it’s home to many vibrant shops and unique restaurants, and the street is always busy.

Foodies can come here for the food crawl, spend literally all day long, and not even try everything.

But besides eateries, you can also pass a few hours pleasantly strolling the avenue, checking out local businesses, and taking pretty photos. With vintage architecture and wondrous Victorian-era houses (like John Palmer House, for example,) Mississippi Avenue is full of spots for Instagram-worthy shots.

Come here in the morning to have breakfast in a well-known brunch destination Gravy which specializes in biscuits and gravy. Next to it, there is a Land Gallery – a local eclectic shop with print art, gifts, shirts, souvenirs, and jewelry. Oh, and don’t forget to grab a blueberry basil bourbon (or any other interesting flavor) donut from another famous place Blue Star Donuts .

VISIT THE GROTTO

From Mississippi Avenue, take a bus or uber to a place of peace, prayer, and natural beauty. Grotto or as the official name goes ‘ the National Sanctuary of Our Sorrow Mother’ is a 62-acre site with a rock-carved grotto with a replica of Mary holding the crucified body of Jesus.

Additionally to the grotto, there is a church, sanctuary, gardens, meditation room, and even hiking trails. A 10-story elevator ride delivers visitors to the top of the nearby mountain with incredible views and stunning chapel.

It’s really nice to walk around here, check the shrine, views, meditate, and reflect. Even if you are not Catholic or Christian, you can still realize a divine feel to this place. On weekends, it gets busy but on weekdays during the morning and early afternoon the sanctuary feels peaceful and uplifting.

If you happen to visit Portland for Christmas, come here to see the Christmas lights. They lit up the entire territory, including trees and grotto and it makes it look like a movie set. Grotto’s website has information on mass schedules, events, and hours. It is a truly fascinating place to visit!

GO TO ROCKY BUTTE NATURAL AREA

Rocky Butte natural area is a small wonderful park with a lookout platform. There, you get a fantastic 360 view of the Columbia River, Portland’s city airport, Mt St. Helen and Mt. Hood. And it feels like the city is laid out in front of you.

If you haven’t seen any of Portland’s city views yet, combine a visit here with a trip to Grotto. With the information standing on the top, you can see exactly what mountains you are looking at.

The only downside of this site is the number of people who come here. Don’t go on Friday, Saturday, or Sunday if you want any sense of privacy. By the way, the cheapest and quickest way to get here from Grotto is by bus.

VISIT MCMENAMIN KENNEDY SCHOOL

From Grotto and Rocky Butte natural area, where you can end up spending a few hours, hop on a bus and proceed to the Concordia neighborhood.

It’s famous for its event center and hotel which used to be an elementary school. If you love visiting architecturally beautiful structures full of history where in addition you can stop for a drink, a movie, or a swim then add this school to your Portland itinerary list.

So as Kennedy School is a hotel today, you can spend a night there. However, you are also welcome to visit as an outside guest.

Grab a beer or a glass of wine in the fancy upstairs bar, enjoy a movie in their theater, soak in their ceramic saltwater pool, dine in a fancy restaurant, or simply walk around the school. Photos and murals of the Kennedy school’s past tell the history and add some mystery to this place.

When we visited, we really regretted we didn’t have our swimsuits. For a very symbolic price (similar to the price of a latte) we could soak in warm waters in the scenic setting. But instead, we walked around for about one hour and checked out all sites.

The Kennedy School is hiding behind the trees and shrubbery, so you can be sure you’ll have a peaceful atmosphere.

STROLL THROUGH BEVERLY CLEARLY SCULPTURE GARDEN

Beverly Clearly Sculpture garden in Grant Park is home to bronze sculptures of Ramona, Henry, and the dog Ribsy who are beloved characters in books of author Beverly Cleary. If you are a fan of these books or visiting Portland with children, it’s a good place to visit on the way to your next destination. Children will definitely have a blast.

The garden is really small. But with a cool sculpture area and fountain nearby it becomes a nice spot on a hot summer day.

There is also a seasonal pool in the park where the general public can swim during the afternoon hours.

VISIT HOLLYWOOD DISTRICT

While the Hollywood district in Portland doesn’t have anything in common with Hollywood boulevard in Los Angeles, it still can be a cool area for a quick visit.

Located only a few streets away from Grant Park, it makes it easy to get here. Since the whole neighborhood is rather small, you can easily roam around it in a few hours. For a really nice acquaintance with another Portland neighborhood full of greenery and lovely homes, start your walk from the north. That area is quiet and calm and you can have a very pleasant walk there under the trees.

Should you be hungry, there are a few places to stop for a meal. Hollywood district is famous for very good Asian food restaurants, so in case you were craving Asian food, the choice is big. Gado Gado family-style restaurant serves very good Indonesian food. Shandong offers Northern Chinese cuisine. The nearby Bluefin Sushi Bar has sushi staples with sashimi and specialty rolls.

Portland’s Hollywood district is also known for its historic 1920s-era Hollywood Theater. If you have a desire and time, come watch a movie here. There are always some classic films, screenings, festivals, and various events that get featured here. This is a perfect place to catch a film in a superbly comfortable environment with relaxing seating. Admissions are cheap, food is good and the building is beautiful.

DO A BREWERY CRAWL

Oh, famous breweries of Portland… they are so famous that many people outside the US know its beers. And that’s not surprising. With nearly 90 percent of US hops coming from Washington state and Northern Oregon, it is easy enough for the state to be a perfect spot for craft beers. In fact, Portland is the number one city in the world with the highest number of breweries in the city. Visiting Portland and not trying the local beer is the same as visiting Istanbul and not tasting kebab.

That being said, you should definitely check out at least one (better a few) breweries. For that, go brewery hopping on your own or join a group tour. Here is an excellent post on all breweries in Portland if you prefer to go on your own. And here are the top 10 beer tours around Portland , some of them offer brewery visits by bike.

Day 4 in Portland

Spend half a day in edgefield.

Edgefield is a beautiful destination resort in Eastern Oregon that is home to a soothing, quiet Ruby’s Spa, Winery & Tasting Room, Distillery Bar, and lovely lodge. It’s easy to forget about the time here and spend one long day.

Come to see restored buildings with cozy interiors and a charming garden with a few hiking trails, play a round of golf, listen to live music, and, of course, sample local wines in the winery. After that, taste great food, get a massage and soak in a pool at the Ruby’s Spa .

The best way to reach Edgefield (if not renting a car) is by bus. It makes a stop right by the McMenamins Edgefield resort.

GO ON A DAY TRIP TO OREGON WATERFALLS

Along with Seattle and Los Angeles , Portland is another West Coast city where you can experience nature (a lot of it!) without going far. Just 20-30 miles east and south of Portland gorgeous waterfalls, trails, forests, and valleys await to be discovered.

One of the most spectacular road trips in America along the Columbia River has its beginning near Portland too. If you don’t have much time to drive all the distance, go and at least see stunning waterfalls. My guide talks about many stops on the Columbia River Gorge drive, including waterfalls. For this reason, you should even rent a car to venture out. Multiple companies also offer various tours if renting a car is not an option. Those who are really short on time can even join a flight tour .

By the way, for the car rental, since the airport is located in the city limits and Columbia River Gorge drive starts right by it, renting a car will save so much of your time!

In any case, no matter what you decide, a visit to Portland cannot be complete without a trip to the incredible Columbia River Gorge. You can skip many suggestions on this itinerary but try to find time for Oregon waterfalls. It’s one of the most beautiful destinations in America!

VISIT WILLAMETTE VALLEY

Willamette Valley is known mainly for the production of the premier Pinot noir wines. However, besides wines as the main reason for people to visit, there are tons of other things to do in the area. Biking, hiking, visiting art galleries, riding a hot air balloon are just some of them. With a charming Inn, it is possible to stay overnight, especially if planning a weekend trip to Portland.

The majority of wineries are located in very close proximity to the city, so reaching them won’t take a lot of time. See this map of the Willamette Valley region to get an idea of where wineries, restaurants, lodges, and spots with activities are located.

If you wish, you can spend your 4th day of Portland itinerary only here. If not, then come for a few hours to taste wines and learn about the production process. In case if having limited time and preferring someone to show you around, join a group tour.

We enjoyed a GreatOregonWineTour company that had stellar reviews and led a very informative tour. I know they are offering tours through Viator and through GetYourGuide . If you are interested, compare prices and see where it’s cheaper. But there are many other fantastic companies to go on a tour with. I highlighted for our future visit BackcountryWine tours and Insiders Wine Tour .

Where to Stay in Portland

Portland has a wide array of accommodation options available. From hostels for budget travelers to chic opulent hotels, everyone can find something on any budget. Yet for the most authentic experience (in my humble opinion,) Victorian-style Inns and privately owned guest houses can make your stay that extra special. So, if you haven’t decided yet where to stay and plan to spend a weekend or all 4 days in Portland, check these options out:

Line and The Rose Victorian Guest House – if you are looking for a luxury stay in Portland and want to stay in a historic vintage home, this Victorian guest house is not to miss! Not only it is located in a very good location close to many restaurants and transit, but it has a magical atmosphere mixed with delightful service. Elegant and comfortable rooms have everything you need for an unforgettable stay.

Check prices and availability for Line and The Rose Victorian Guest House on Booking.com

Hotel Vintage – an upscale trendy hotel in the center of downtown Portland. With modern unique design details, chic suites, a pool, restaurant with local wines, and craft beers, this hotel is a great place to stay if besides the city explorations you would like to have a hotel getaway.

Check prices and availability for Hotel Vintage on Booking.com

McMenamins Crystal Hotel – for a comfortable and top-notch stay for a budget-friendly price you have to check this quirky hotel in downtown Portland. The decor in all rooms here has been influenced by the show ‘From Blondie to The Flaming Lips’ which is performed in The Crystal Ballroom just across the road.

Their spotless rooms, lovely indoor swimming pool, music-themed art gallery, lovely restaurant, own selection of crafted beers, and outstanding service make it one of the best hotels to stay in Portland.

Check prices and availability for McMenamins Crystal Hotel on Booking.com

HI – Portland Northwest Hostel – an excellent choice for travelers on a tight budget or those who are looking for a “community” type of experience. Located not far from the famous Mississippi Avenue, it has clean, comfortable rooms with all the necessary amenities.

Based on excellent reviews, this hostel has outstanding service and the staff makes you feel like staying with friends. Check reviews and prices here .

Check prices and availability for HI – Portland Northwest Hostel on Booking.com

Don’t feel like any of these accommodation options is right for you? Click here to browse other hotels in Portland .

Planning your perfect weekend Portland itinerary can take some time. There are so many things to do in the city! But if you follow my tips, you’ll surely have an amazing trip to Portland!

If traveling from outside the US, don’t forget to take care of your travel insurance to know you are covered for any event. We personally like to stick to SafetyWing, click here to get a quote from them .

Are you planning a 1, 2, 3, or 4 days in Portland itinerary? Or maybe you are planning to spend more days in this city? Have you visited Portland before? Share in the comments!

Did you find this post helpful? Don’t forget to pin it!

This 2 to 4-day Portland itinerary will ensure that you get the most out of your trip! | Portland Oregon | West Coast | Best Cities in USA #westcoastroadtrip #portlandoregon #oregontravel

Anya is originally from Ukraine but in heart she is a citizen of the world. She is working online and that’s why has an opportunity to travel a lot and live in different countries. At present time, she is based in Spain while waiting for the war in Ukraine to be over to be able to return home. On this blog, her main goal is to inspire others to travel to under-the-radar places and discover the world while working remotely.

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I enjoy reading this blog, a cool place. Thanks for the travel tips for Portland, and for sharing your journey.

I love Portland. I work here as a wedding photographer. Lots of couples come here for the weekend to elope. I help them find all the best views of the city for some interesting wedding photos. It’s a lot of fun.

2 Days in Portland, Oregon a great Portland itinerary

This post is also available in: French

Portland, Oregon, is home to one of the world’s largest bookstores, some of the most famous doughnut shops, and a vibrant craft beer scene. It also has some incredible parks within city limits as well as plenty of outdoor pursuits within a short drive, including the Columbia River Gorge and Multnomah Falls. The local orchards and hopyards provide both wineries and breweries with plenty of hops and fruit, while the city’s doughnut and ice cream producers provide Portlanders with all kinds of delicious treats.

Table of Contents

How to spend two days in Portland, Oregon

2 days in portland: day one, chinese gardens.

The Lan Su Chinese Garden is located in the northern heart of downtown Portland, a few blocks from Powell’s and Voodoo Donuts. It is a collaboration between Portland and Suzhou, Portland’s sister city in China’s Jiangsu province. Suzhou is famous for its beautiful Ming Dynasty gardens. Portland’s Lan Su was built by Chinese artisans from Suzhou and is considered to be one of the most authentic Chinese gardens outside of China. Your entry ticket includes a public tour of the garden with a trained docent, which is one of the best ways to learn the secrets of Lan Su.

Voodoo Donuts

Voodoo donuts is an independent donut shop in Portland. Opened in 2003, the shop is known for its unusual varieties and twists on classic donuts. While they now have locations in several places across the US, nothing beats going to the original shop in Portland’s old town.

Powell’s City of Books

For book lovers, Powell’s is an icon, a Mecca of sorts, and it’s nicknamed the City of Books. Taking up nearly one entire city block, rising several stories high, and encompassing nine rooms over 68,000 square feet, the bookstore is more than just a store. Powell’s has a used book sales department, reading rooms, cafe, and more. The store provides a map (you’ll need one) and from there you browse to your heart’s delight.

Get ice cream in Salt and Straw

Salt and Straw describe themselves as “curiously delicious ice cream made by hand with local ingredients,” and in true Portland style, they are all about the experience. Flavors change often and sometimes disappear forever, and the team is endlessly pushing the boundaries of unique tastes.

Pearl District with Amazing Boutiques

The Pearl District is located on the west side of Portland, just south of the Willamette River, and is known for having plenty of great shopping. Originally a rundown neighborhood with abandoned warehouses and a rising crime rate, the Pearl District is now among the most fashionable in the city. Find one of a kind artwork, jewelry, and more within the district, dine at fantastic restaurants, drink at the craft breweries, and experience the urban renaissance that is the Pearl.

Check out the food carts around the city

Portland is well known for its many food carts. Whether you are after lunch or dinner, a stop at a Portland food cart is authentic and delicious. Most food carts stick together in what Portlanders call pods, so it’s easy to sample several dishes at one time. You can find pods of food carts at Pioneer Square, 5th Avenue, Portland Mercado, and Portland State University.

2 days in Portland: Day Two

The Oregon Museum of Science and Industry (OMSI) is located on the eastern side of the river, across from downtown Portland. It is a large museum dedicated to both natural and manmade sciences. Be sure to visit the submarine, which is a permanent part of the museum and offers daily all-encompassing tours, daily tech tours, and occasional sleepovers. If you’ve ever wanted to overnight on a submarine, you can do it at OMSI.

Washington Park

Washington Park is located in the west hills of Portland. It is a vast park – over 400 acres – with many trails to walk around, the aforementioned Japanese Garden, a zoo, forestry museum, arboretum, tennis courts, memorials, and more. The land that the park sits on was bought in the late 1800s and was transformed into a rudimentary park with trails, flower gardens, and manicured hedges. But it wasn’t until the early 1900s, when the Olmsted Brothers made some changes, that the park really took off in shape, size, and structure. Today, the Japanese Garden occupies the site of the original zoo, and the original OMSI is now a children’s museum. The park is open until 10 pm and is a great place to spend a few hours after exploring the city of Portland.

Rose Garden

The rose garden in Washington Park is no ordinary rose garden. It is an international test rose garden, which means that rose cultivars are sent to the garden from many parts of the world. These are evaluated on several characteristics, including disease resistance, bloom formation, color, and fragrance. It is the oldest continually operated test rose garden in the US and came about during the First World War when someone convinced the city to protect hybrids grown in Europe at this time. The garden now has over 10,000 rose bushes in over 650 varieties of roses and it is exemplary of Portland’s nickname, the City of Roses.

Japanese Garden

The Japanese garden is located within Washington Park in the west hills of Portland. The 12-acre garden has eight different garden spaces and a cultural village. Some of the most popular gardens include the strolling pond garden, which features a five-tiered pagoda lantern gifted by sister city Sapporo.

The various gardens have ponds, waterfalls, stone gardens, and plants. Portland’s Japanese garden is open daily throughout the year and offers free tours every day at noon. The park does charge admission.

Pittock Mansion

Built in 1914, the 46-room Pittock Mansion sits on 46 acres in the West Hills of Portland. It was built by the Oregonian publisher Henry Pittock and his wife Georgiana. The exterior is a blend of French Renaissance and Victorian architecture, while the interiors pull influences from different eras of English history as well as Turkish and French design. Georgiana Pittock was a founding member of the Portland Rose Society, and the exterior gardens are full of roses to commemorate her influence.

Taste the “Best Reuben on the Planet” at the Goose Hollow Inn

The Goose Hollow Inn, located on the west side of Portland, is a classic tavern (no hotel rooms) with some of the best food in town. It was opened by the former mayor of Portland, Bud Clark, and remains a popular spot for locals and visitors. The interior is cozy and warm, with photos of local celebrities all over the walls, while the tavern also boasts a great outdoor terrace open in the summer.

Check out the Breweries

Portland is one of the best cities for craft breweries, so be sure to take some time to explore them. At last count, there were over 60 breweries started in Portland, which means you’ve got your work cut out for you. And no matter your taste in beer, you will find something for you – sours at Cascade, farmhouse-style ales at Upright, or IPAs at most of the breweries in the city.

Go Shopping

Oregon is sales-tax-free, meaning that purchases like clothes, home goods, and more incur no sales tax. This is a great place to stock up on some cute items at the Pearl District boutiques!

Day trips from Portland

Portland has many great day trips nearby, from the Willamette wine region to the rugged coast. If you have extra time, you can check out these local Portland day trips.

Visit Latourell Falls

Latourell Falls is one of the closest waterfalls to Portland in the Columbia Gorge, and one of the most picturesque. There is a loop trail of about two and a half miles that get hikers to Upper Latourell Falls and back down to the base of the falls below the highway. There is a moderate elevation gain and the trail is both well-marked and well-maintained, making it an easy half-day trip from Portland city center.

Columbia Gorge

If you have the whole day, you can go out further into the gorge and visit sites like Multnomah Falls and Punchbowl Falls, the historic towns of The Dalles and Hood River, and see one of America’s most scenic canyons. The Columbia River Gorge is a full experience, from the jaw-dropping scenery to the exceptional food and wine you can find here (and the craft beer), and to the adventure, you’ll come across.

Cannon Beach

Cannon Beach lies about a two-hour drive from Portland and is a charming seaside town with a wide, flat beach and two haystack rocks out in the sea. The town has plenty of great shops and restaurants and makes a delightful day out.

How To Get into Portland From the Airport

The most inexpensive way to get into the city center from Portland Airport is by the MAX light rail, which only takes about 40 minutes and runs 20 hours of the day. There are stations all across the city. An adult ticket costs less than $5.

A taxi is the most convenient way to get into the city, since it’s a door to door service, but will cost approximately $35-40.

Portland is a fun city for a long weekend. It has incredible dining options, great craft breweries, excellent shopping, plenty of city center wilderness, and a lot of exciting day trips. Whether you are in town on business and need some foodie inspiration or want to Instagram your way across the city, this two days in Portland guide has all the right ideas for you.

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If you revisit Oregon you should definitely check out the Willamette Valley. A great alternative to Napa Valley. Tastings are much more affordable, the scenery is incredible, and the vibe is much more casual and intimate. I’m from there and wrote an in-depth post on how to spend a wine weekend in Willamette Valley. Let me know if you think of visiting!

The Ultimate Oregon Road Trip: Itinerary Inspiration and Must-See Stops

last Updated: May 17, 2021 bend cannon beach crater lake mt hood oregon portland road trip

FYI: Affiliate links may be sprinkled throughout the awesome, free content you see below. I’ll receive a small commission when you purchase from my links (at no extra cost to you), which I’ll totally blow on adult things like boba tea and avocado toast. As always, thanks for the support.

Are you ready to be blown away by shimmering lakes, snowy mountain tops, and enough craft beer to last a lifetime? Get ready for an Oregon road trip, my Pacific-Northwest-craving friends. Sharing tons of details below to get you started planning your trip to the Oregon coast and beyond!

Just last year I had never visited Oregon before. Yeah, yeah, shame on me (I kiiinda recently moved to the west coast so you’ll cut me some slack, yea?) ;p I visited for the first time last year, and let’s just say I’m a tad obsessed. I had heard Portland was kinda cool, and after one look at Crater Lake I knew I had to make it there sooner than later. Alas, my first few trips to Oregon were planned, and I’ve now found myself in the state 3 times within a ~6 month period (something that just NEVER happens).

Heading to Oregon and wondering what all the things to do in Crater Lake are?! Click through for the best hikes, best viewpoints, where to stay, and what to eat - exactly what you need to plan your own visit to Crater Lake!

So without further ado, I’m sharing my ideal Oregon road trip, from the quirkiness that is Portland south to the dazzling still water of Crater Lake and west to the allure that is the stunning Oregon coast.

Oregon Road Trip Itinerary Overview

Stop 1: Portland (2-3 days)
Stop 2: Columbia River Gorge/Multnomah Falls (1 day)
Stop 3: Mt. Hood (1 day)
Stop 4: Silver Falls State Park (1 day)
Stop 5: Smith Rock State Park (½-1 day)
Stop 6: Painted Hills (½ day)
Stop 7: Bend (1-2 days)
Stop 8: Crater Lake (1-2 days)
Stop 9: Ashland (1 day)
Stop 10: Coos Bay / Southern Oregon Coast (1 day)
Stop 11: Newport, Tillamook, and Cannon Beach (1-2 days)
END: Portland

Over the course of the road trip, expect to drive approximately 24 hours (round trip) and around 1000 miles. You’ll notice on the map below that I haven’t included the drive from Portland to Silver Falls State Park (that’ll add another 2 hours or so to the time listed on the map), as well as the 1.5 hour drive back to Portland from Cannon Beach (limits of technology). In order to complete this Oregon road trip in a timely manner (a week to 10 days or so), you’ll be driving almost every day, with some being longer driving days than others. Plan accordingly and bring snacks! The time in the car doesn’t have to be absolutely horrible. :p

→ Read next: Top Tips for Long Car Trips // Long Road Trip Essentials

Planning an Oregon road trip? This post has everything you need, from where to stop, where to sleep, and top things to do in each place!

When to Visit Oregon

Like the rest of the Pacific Northwest, Oregon experiences four seasons. To be completely transparent (and as noted above), I visited these different spots in the state on a few different occasions. I visited Portland in early June, Crater Lake in early September, and Bend in the snowy winter months. Oregon is spectacular year round, but if you’re on the hunt for some sunshine and minimal precipitation, I’d recommend planning your Oregon road trip between the months of April and September.

The best month for visiting the Oregon Coast is typically September, as the summer months are usually pretty foggy. It’ll be the wettest throughout the state between November and March, and the warmest between June and September. The roads around Crater Lake typically don’t fully open to cars until July, so keep this in mind if you’re visiting prior!

Planning a trip to Oregon in the near future? Check out this Portland itinerary, full of great foodie spots, waterfall hikes, and vista points! See all the highlights in 3 days in Portland!

If you have the luxury of picking exactly when to take your Oregon road trip, choose September! The weather is glorious – little to no rain, clear coastlines, and warm weather. Just like my home state of California, Oregon typically experiences an Indian Summer, which lasts until early-mid October.

Getting to Oregon (and Portland in particular)

First things first, if you’re not a resident of Oregon, you’ll of course need to get yourself there! Since PDX is a major international airport, it’s wise to start your Oregon road trip in Portland, as you’ll be able to find decently priced tickets from throughout the US, highly dependent on the airport you’re departing from. For reference, from SFO (San Francisco), I commonly see round trip tickets to PDX (Portland) for under $200, and many times under $150.

New Yorkers can fly to Portland for roughly $300 if bought far enough in advance. I swear by Skyscanner and Google Flights whenever searching for tickets, and more often times than not, find the cheapest prices on one of them. The ability to track prices (and get email notifications when the price drops) is top notch and one of my favorite features. Take advantage of Skyscanner , you guys, they’re seriously the best.

quirky coffee shops everywhere you go in Portland – this one’s in a converted school bus!

If you’ll be following this complete Oregon road trip itinerary you’ll be doing a full loop from Portland, hence the need for round trip tickets from PDX. If you’re coming from Northern California and don’t mind doing a bit of extra driving, you can start this road trip from wherever you see fit (Crater Lake is roughly 7-8 hours from San Francisco, and the southern Oregon Coast – Coos Bay – is about 9 hours). Just remember that you’ll need to head back to your original destination. 🙂

Since this is in fact a road trip , you’ll need a vehicle to get you from place to place! Worth mentioning so you don’t forget to account for the cost of a rental car when following this Oregon road trip! And since you’ll be returning the car in the same place you picked it up, no need for pesky extra drop-off fees. I commonly use this booking site when searching for low-cost car rental options, and like Skyscanner , frequently find great deals on there!

I like to search via this site in order to compare rental companies to see who has the best price.

How Long Should This Oregon Road Trip Take?

In all honesty, that’s a kinda hard question to answer, as the duration of the trip highly depends on your interests and how long you wanna stay in each place. I’d say a week if you’re picking and choosing a few stops to 2 and a half weeks if you wanna see and do mostly everything on this Oregon itinerary at a leisurely pace.

Now let’s get this Oregon road trip under way!

The Complete Oregon Road Trip Itinerary

Stop #1: start in portland (2-3 days).

Portland, Oregon is best known for its delectable donuts, snobby coffee culture, orgasmic food, and, of course, for being weird. It is in their slogan after all! Two to three days in the city will give you enough time to see all the highlights, as well as eat to your heart’s content. It’s the best place to start your Oregon road trip since renting a car will be easy peasy if you’re flying into PDX.

With two days in Portland, you can easily fit in these activities:

Pittock Mansion: Looking for spectacular views of the entire city? You’ll find those here at Pittock Mansion. Note that while the view is free to admire, a ticket is required to tour the mansion grounds.

International Rose Test Garden (located within Washington Park): What’s better than rows and rows of sweet-smelling roses? Hint: not much. The garden boasts over 10,000 of the pretty things, in every color combination imaginable (over 650 varieties)! Wander around for a half hour or so, and be sure to actually stop and smell the roses (yes, pun intended). Make sure you visit when the roses are in bloom (April through October, although June is the peak season). FYI – Entrance to the garden is free, but you’ll need to pay a few bucks for parking.

Powell’s City of Books: Book lovers, rejoice! You can easily spend hours (and hours) exploring Powell’s flagship store – you’ll even need a map (which they happily supply). Be warned: this place is HUGE huge (like, multiple floors with rooms opening into rooms opening into rooms, etc etc). It actually takes up an entire city block and then some. If you can’t find what you’re looking for, you’re just not looking hard enough – they have EVERYTHING imaginable and then some (new, used, rare, and even out-of-print books). I was like a kid in a candy store…

Keep Portland Weird Sign: Right across from Voodoo Donuts you’ll find this quick photo spot → don’t miss this iconic mural! The sign itself is just a wall in a parking lot, but just go, be weird, and take your picture. The actual address is 350 W Burnside St in case you can’t find it (it’s right behind Dante’s).

Tilikum Crossing: Have more time and looking for a scenic leisurely walk over the river? Head to Tilikum Crossing, also known as the “bridge of the people”, a .35 mile pedestrian, bike, and light rail bridge with unparalleled views of the Willamette River. Smart, right? Why don’t more cities have this (bridges that ban cars that is)? You can easily do this walk back and forth in under an hour. I reckon it’d be even more dramatic and scenic at night with all the city lights shining down on the river! Be sure to look out for the submarine near OSMI!

→ Read Next: 3 Perfect Days in Portland

Where (and what) to eat in Portland (my favorites):

Pok Pok: order the Vietnamese fish sauce wings
Blue Star Donuts: just do it, more than once (calories don’t count on vacation)
Coffee at Stumptown: grab some at the airport if you don’t have time
Salt and Straw ice cream: try some of their wacky flavors, changing all the time!
Abyssinian Kitchen: some of the tastiest Ethiopian food around
Katchka (Russian): try the herring under a fur coat, Siberian dumplings, lamb with rice, and cauliflower schnitzel (all super tasty)
Pine State Biscuits: I’m drooling just thinking about my breakfast
Fried Egg, I’m in Love: the best egg sandwiches in Portland, in my opinion
Tov Coffee: located in a converted school bus; get “the mint thing”, it’s orgasmic
Voodoo Donut: a Portland must-stop, even if everyone says Blue Star is better

Sleep: Portland (I’ve been lucky enough to stay with friends/family when visiting the area, but I’ve heard fantastic things about Ace Hotel Portland , Jupiter Hotel , Kimpton Hotel Monaco , and Stay Pineapple at Hotel Rose . Browse all hotels in Portland here .

Stop #2: Multnomah Falls and the Columbia River Gorge (1 day)

Distance: 30 miles to Multnomah Falls | Driving time: 45 minutes + driving through the Gorge

It’s time to grab those wheels (hint: car rental) and make our way towards our first official stop on this Oregon road trip, Multnomah Falls!

Being the tallest waterfall in all of Oregon state, a stop at Multnomah Falls really should be on any Oregon road trip itinerary, no matter how long or short. Looking up at the 600+ foot tall roaring cascade of icy water is awe-inspiring to say the least! It’s actually the most visited natural recreation site in the Pacific Northwest (whoaaa Nelly), so be prepared to share the views with 34,534 of your closest Portland-loving friends if you come after 10am. Visit before 9am and you’ll have the place almost to yourselves, season dependent.

Once Multnomah Falls is outta the way (and as noted earlier, head here early due to the crowds that arrive by 9/10am), continue on your waterfall-finding journey – there’s dozens upon dozens (!!!) of them in the Columbia River Gorge. The Gorge is essentially a canyon of the Columbia River, stretching more than 80 miles and up to 4,000 feet deep, and is kinda a divide between Washington and Oregon. With stunning vistas and enough waterfalls to last a lifetime, you’ll want to carve out at least half a day to explore.

Note that trails close on occasion due to wildfires, so you’ll want to make sure access is available before you set off on any hike. I’ve heard Horsetail Falls, Latourell Falls (it’s a few minutes before Multnomah, but go afterwards to beat the rush at Multnomah), and Wahkeena Falls are spectacular – but all were closed during my June 2018 visit due to the horrific fire in 2017. Check for possible trail closures here .

Note that it’s about 45 minutes from Multnomah Falls to the town of Hood River, which is a good place to base yourself for the night. If you’re exploring other waterfalls in the Gorge, you’ll be even closer to Hood River.

Sleep: Hood River (Check out the Hampton Inn & Suites Hood River and the Best Western Plus Hood River – both great options). Browse all hotels near Hood River here.

Stop #3: Hood River and Mt. Hood (1 day)

Psst – if you’re really pressed for time you can combine stop #2 and #3 into one long day. It’s definitely doable, it’ll just be a little rushed. Do note that if you plan on doing some hiking, you’ll probably wanna split up the days, but your call! I visited everything in one day, but wasn’t able to do all the hiking I wanted due to the trail closures as mentioned above.

Distance: 47 miles to Timberline Lodge | Driving time: 1hr

Next up, Hood River, but first, a short pit stop at Rowena Crest . Sure, it’s about 25 minutes outta the way, but most definitely worth it for that instashot (I’m sure you’ve seen it somewhere – haha)! So what is it about this place that makes it rather popular?! Yes, it’s technically just a bend in the road but the surrounding scenery makes it a worthwhile stop.

This iconic horseshoe curve is actually one of the most photographed roads in all of Oregon! It does get pretty windy up here, so if you’re planning on taking that insta-photo, please be extra extra careful! Note that you’ll need to hoist yourself up and over the railing if you want more than just shoes in your shot (I was too much of a chicken to do so).

On your way to Mt. Hood, you’ll most likely wanna stop in Hood River for some lunch. My suggestion – Solstice Wood Fire Cafe for, you guessed it, some wood-fired pizza. Stretch those legs and go for a walk along the Hood River Waterfront for some great views of the area as well!

Additional pit stop: Hood River Lavender Farm ! An absolute must-stop for anyone who’s even a little bit lavender obsessed. Not only can you wander around the whole place smelling the sweet smells, but for $5, you can pick your own lavender to tie up and bring home! The place was smaller than I had expected, but there’s tons and tons of lavender bushes so it doesn’t even matter. Be extra careful when picking, as there’s lots of bees!

Be sure to look inside the gift shop for lavender jams/jellies, soaps, etc. If you come on a clear day you can even see Mt. Hood in the distance! FYI: Lavender picking season is from April/May to November, with peak bloom being July-August.

Wanna brag to your friends about finding the best views of Mt. Hood? Head to Trillium Lake , where the mountain literally reflects in the water and creates the most peaceful setting. What’s better than a mountain reflection in a jazzy blue lake? Not much! On a clear day, you’ll find Mt. Hood perfectly reflected in the water. Worth the short photo stop for sure! You can also walk around the lake for additional views as well, but we wanted to make it back by dinner so skipped the almost-2-mile loop trail. I want to visit during sunrise or sunset next time!

End this long day at Timberline , a mountain lodge right at the base of Mt. Hood, where you can watch the skiers summer ski and grab a bite to eat (if you’re so inclined). You of course can spend the night here if you’re planning on actually using the mountain for skiing or snowboarding (be sure to make reservations in advance), but we were just observers for the day.

Sleep in Mt Hood : Timberline Lodge if you’re feelin’ fancy, or check out Best Western Mt. Hood Inn or Collins Lake Resort for budget options in the area.

Stop #4 ( optional ): Silver Falls State Park (1 day)

(adds an extra 2-3 hours of driving time)

Distance : 94 miles to Silver Falls State Park | Driving time : 2hr plus traffic

→ Note that it’s more than possible to visit Silver Falls State Park as a day trip from Portland, so if you wanna do that and tack on a day to your Portland stop, feel free! → That’s what I did! It’s actually only about 1 hour, 15 minutes south of Portland, so if you prefer staying in the city and switching hotels one less time, a day trip to Silver Falls from Portland may be your best bet!

If the waterfall at Multnomah wasn’t enough for you, or you’re just a waterfall fanatic like myself, make the 2-3 hour detour to Silver Falls State Park. (Psst – I actually found the waterfall at Silver Falls State Park even more spectacular than those on the Columbia River Gorge). There are numerous trails available, with the easiest of them leading to the most impressive waterfall in the park – South Falls. You can even go behind some of them! Definitely reminded me of the some of the waterfalls I saw in Iceland!

If you’re looking for a longer hike, trek the entire 9 miles and you’ll be rewarded with 10 waterfalls (yes, 10!). Where else can you see 10 waterfalls on one hike?! We hiked about 3 miles or so and saw two waterfalls.

People actually call it the “crown jewel” of the Oregon State Parks system – you’ll quickly understand why after your first visit! I mean, who doesn’t appreciate a leisurely walk the rainforest (Oregon’s only one actually!)

Sleep : Browse all hotels near Silver Falls State Park here.

Stop #5: Smith Rock State Park (½ – 1 day)

Drive: 3 hours to Smith Rock State Park from Silver Falls State Park -or- 2 hours from Timberline

Located roughly 30 minutes north of Bend (next up on this Oregon road trip itinerary) in central Oregon’s High Desert (riiiight off the highway I might add), this is a spot you’d be absolutely mistaken to miss, no matter the weather. With scenic views of deep river canyons and ample hiking opportunities, Smith Rock is any outdoor-lovers dream. If you’re up for a workout on tons of switchbacks, head up to Misery Ridge for dramatic views of the entire canyon and nearby rock formations. This spot is a mecca for rock climbers, and even if you don’t subject yourself to Misery Ridge (it is called Misery Ridge for a reason), you can still spot them from the canyon floor.

Things to do in Bend, Oregon: A Wintery Guide to the City and Surrounding Areas (including where to stay, how to get around, where to eat, and lots more!)

we visited in winter, hence the reason we’re bundling up (obv)

Psst: if you’re an alpaca fanatic like I am (guilty!), be sure to check out Crescent Moon Ranch located in Terrebonne (right near Smith Rock State Park). make sure to head into the visitor’s lounge to pick up some alpaca food to feed the little guys and check out all the goods made from their soft, luxurious fleece. Wool sweaters, wool socks, wool stuffed animals, and oh so much more – it’s all there.

Sleep: near Smith Rock ( Sleep Inn & Suites Redmond and Best Western Plus Rama Inn are viable options) or in the areas of Mitchell / Prineville near the Painted Hills (depends if you wanna do more driving today)

Stop #6 ( optional ): Painted Hills and surrounding areas (1 day)

This minor detour to Painted Hills will take you roughly an hour and 45 minutes outta the way, but hey, you might as well see a lot of the state on this Oregon road trip. And plus, it’s one of the Seven Wonders of Oregon, so you kinda gotta see it.

The Painted Hills are just that – full of hills of a whole myriad of different colored soils, including yellows, golds, blacks, and reds. Top Tip: these different colors are best viewed in the late afternoon (the claystones appear different dependent on light and moisture).

But don’t leave just yet – the Painted Hills are just one of three units that make up the John Day Fossil Beds. You’ll find mars-like landscapes at the Clarno Unit, and fossils of plants and animals at the Sheep Rock Unit (which make up 55 million years of evolution with a giant collection of 40,000 fossils). And no, I didn’t exaggerate those numbers. It’s the real deal over in these parts! All of these three units have short trails to dramatic viewpoints of colorful rock formations – you could easily spend all day here. Note that the three units are roughly 1 hour away from each other, so you’ll need to account for some extra driving should you want to visit two or all three.

→ Important: If you’re staying after dark to watch the sunset (highly recommended), be extra careful when driving to your accommodations at night. There’s lots of wildlife out and about near the roads (deer, elk, etc).

Note that today’s kinda a lot of driving if you decide to see Smith Rock and the Painted Hills in one day, so you may want to consider sleeping in Mitchell near the Painted Hills (30 min drive) and driving to Bend the next morning. If you wanna get a head start the drive to Bend, sleep in Prineville (roughly 1 hr, 15 minutes from the Painted Hills and on the way to Bend).

Sleep : Bend at LOGE Entrada Bend (where I stayed and brand spankin-new) or The Oxford Hotel (another top-notch option recommended by a couple we met on our Craft Beverage Tour). Browse all hotels in Bend here . (or Mitchell / Prineville near the Painted Hills)

Stop #7: Bend (2-3 days)

Drive: 2 hours to Bend from the Painted Hills

Located between the snow-covered peaks of the Cascade Mountains and the high desert plateaus of Central Oregon, Bend really has it all, and then some. Because of its prime location for outdoor activities (think hiking, biking, river sports, etc), you’ll find a ton of sporty enthusiasts living the rugged lifestyle.

Bend is basically an adults playground. And the town is super cute, too, with a whole slew of mouthwatering restaurants and cafes to indulge in!

As noted above, we visited Bend in it’s snowy winter months , and have yet to experience the area in all it’s warm-weather summer-glory. We fully enjoyed our time in Bend covered in snow, and went snowshoeing, took a craft beverage tour, and ate everything in sight (for real).

However, since I have a feeling you’ll be planning this Oregon road trip for a warmer month, I’ve compiled some of the best things to do in Bend sans piles and piles of snow. I have a few friends and cousins who frequent the area quite often (they’re Bend-obsessed), so I got some recommendations from them for you to enjoy.

Since Bend is sooo well known for its craft beers, you can’t leave town without taking part in the fun for at least a little while. The city is actually known as Beer Town USA, and has more breweries per capita than any other city in Oregon. Craft beverage tours like the Bend Ale Trail or the Local Pour Tour with Wanderlust Tours are especially popular to sample local sips.

We loved the mixture of the Local Pour Tour, visiting a local cidery, kombucha tap room, a whisky distillery, and of course a brewery. There’s even a non-alcoholic beer brewed for pups! Crazy, right?! They do love their beer over in Bend! If you’re a beer fanatic as well, you may want to schedule your trip to Bend during one of it’s many annual beer celebrations, including Central Oregon Beer Week, Bend BrewFest, or Bend Oktoberfest (among many, many more).

Alternatively, simply wander around the Old Mill District and Downtown Bend, which have tons of places to eat, stroll, or shop.

Outdoor lovers will also find tons to do here. During the summer, book a kayaking or canoeing expedition on the Cascade Lakes or the Deschutes River with Wanderlust Tours, who we actually went snowshoeing with in the winter and LOVED!

You can also enjoy the outdoors on foot or by bike, and you’ll see tons of people out on the trails on warm, sunny days. The Pilot Butte Trail is a popular hiking trail in Bend that takes you to the top of an extinct volcano (yup, I said volcano alright), with thrilling views of the surrounding Cascade Mountains nearby. It’s a beautiful, scenic trail for beginners and seasoned hikers alike. For bikers, you can’t beat the Deschutes River Trail, which extends over 12 miles and borders the Deschutes River, winding through canyons and beautiful green forests along the way.

what you can expect Bend to look like in the winter (that snow, swoon)

And if you’re looking to amp up your photography skills, book yourself a private lesson with Toni from Bend Photo Tours. She was oh so patient with me and answered all my silly (and quite embarrassing) questions without batting an eye. Next time I’m there I’m hoping the weather conditions are sufficient for some night-sky photography!

→ Read Next: A Snowy Weekend Trip to Bend, Oregon

Sleep: Bend at LOGE Entrada Bend (where I stayed and brand spankin-new) or The Oxford Hotel (another top-notch option recommended by a couple we met on our Craft Beverage Tour). Browse all hotels in Bend here .

Stop #8: Crater Lake National Park (2 days)

Drive: 2 hours, 30 minutes to Crater Lake National Park from Bend

Crater Lake National Park has got to be one of the most mesmerizing places I’ve been to date, and thankfully, it’s up next on this Oregon road trip. With its calm dazzling blue waters, scenic highways, and super starry night skies, you can be sure you’ll never forget your visit to Crater Lake. And that’s a promise!

Some quick facts:

Crater Lake is currently the 10th-deepest lake in the world, with a maximum depth of almost 600 meters (1,949 feet). It’s also the deepest lake in the USA!
The magnificent intense blue color of Crater Lake is primarily due to it’s great, great depth, and remarkable clarity. The waters stay so clear since the lake has no other bodies of water flowing into it, meaning little-to-no pollution!

We spent most of our time hiking, but there’s lot more to do at the National Park if hiking isn’t your jam. Revel in the views from Rim Drive’s multitude of lookout points, get some fancy drinks and/or a dessert at Crater Lake Lodge, take a boat cruise to Wizard Island, and even go for a swim (if you dare to step foot in the chilly waters)!

Although the park is open every single day of the year, many of the park’s roads, trails, and facilities are closed seasonally due to snow, which usually do not reopen until summer (June/July). If you want to ensure you’ll be able to drive around the perimeter of the lake (Rim Drive), schedule your trip for late July, August, or September. These also happen to be the most popular times to visit Crater Lake, but don’t fret – the park is rather large so you’ll still be able to find your own spots of peace and solitude.

Sleep : Melita’s Crater Lake Lodge nearby Crater Lake (or you can head right to Ashland if you prefer). Browse all hotels near Crater Lake National Park here.

Stop #9: Ashland (1 day) – OPTIONAL

Drive: 2 hours to Ashland from Crater Lake National Park

Get one last look at Crater Lake, then hit the road; it’s time to make our way to Ashland, one of southern Oregon’s hot spots and loved by all.

Ashland is a classic Pacific Northwest hippie town with a love for nature, beer, and admittedly, all things weird. Here, you can find a very alternative vibe, with tons of green, vegan health shops, locally-brewed beers, and tons of places where you can get in touch with the quirky and downright strange personality of the place.

It’s not everywhere that you can watch Shakespeare, drink Sriracha flavored beer, and go to a paranormal activity hotspot in just one day. But in Ashland, you can do all this and more! Told you it was weird.

Speaking of Shakespeare, The Oregon Shakespeare Festival (OSF) is a must-see here, with regular shows at the Green Show, a performance venue and courtyard that’s frequented by visitors and locals alike. But if you’re not a fan of Shakespeare himself (say what?!), you can see other productions the group puts on, like Hairspray and Alice in Wonderland. The OSF shows usually happen during the summer, and if you choose to go to a classic Shakespeare show, don’t miss the ones at the Allen Elizabethan Theatre.

Aside from Shakespeare, there are tons of other weird and wacky things to do in Ashland. Beer lovers can find the strangest and most unique beers at the Caldera Brewing Tap House, a local favorite that made waves with its Sriracha Stout beer. You can also visit the Oregon Vortex, which is a weirdly spiritual spot known for paranormal activity and other strange happenings located about 30 minutes from town. And of course, don’t forget to enjoy the beautiful nature in the area, especially in the fall, when the leaves turn all kinds of beautiful colors.

Technically , if you wanna save a bit of driving and don’t have all the time in the world, you may choose to cut Ashland out of your Oregon itinerary. Your call, but I think it’s worth at least a day or so.

Sleep: Bard’s Inn Ashland . Browse all hotels in Ashland here.

Stop #10: Coos Bay // Southern Oregon Coast (1-2 days)

Drive: 3 hours, 15 minutes from Ashland to Coos Bay

It’s finally time to get this Oregon coast road trip itinerary underway! The drive from Ashland and Crater Lake will essentially take the same amount of time, so there’s no absolute NEED to visit Ashland if you’re pressed on time. If you’re coming from either one, you have two options – the long way (~5 hour drive with more exploration of the southern Oregon coast), or the shorter way (3 and a half hours cutting straight to Coos Bay from Ashland/Crater Lake). I suggest opting for the short route as in my opinion, you won’t be missing out on too much by skipping the southern coast below (as Coos Bay is one of most scenic areas on the Oregon Coast)– but obviously, your choice!

San Francisco to Seattle Road Trip Itinerary: COMPLETE road trip with all stops, where to stay, and top things to do from San Francisco to Seattle (national parks, stunning lakes, best wine, etc)!

Coos Bay is home to the Cape Arago Beach Loop, which is where I’d spend the rest of the day.

On this driving/exploring/sightseeing loop, you’ll venture into three Oregon State Parks, watch a ton of seals and sea lions play, as well as stop at numerous breathtaking vantage points. The drive is not super long, but you’ll definitely want the better portion of the day to stop and soak it all in!

A few must-see stops: 1) Bastendorff Beach (say goodbye to crowds and hello to oh so much natural beauty), 2) Sunset Bay State Park (those towering sea cliffs sure are something, especially with the beautiful sandy beaches and amazing tide pool explorations), 3) Cape Arago Lighthouse Viewpoint (you unfortunately can’t view the inside but you can get fantastic views from here), 4) Shore Acres State Park and Botanical Gardens (tons and tons of blooms), 5) Simpson Beach (look out for the migrating whales and hundreds of seals and sea lions), 6) Shell Island (breeding and rest areas for seabirds and Marine mammals), and finally 7) Cape Arago State Park.

Sleep in Coos Bay : Browse all hotels near Coos Bay here.

Stop #11: Newport, Tillamook, and Cannon Beach (2 days)

Next up on this Oregon coast road trip → making the way back up north to Cannon Beach!

Prepare yourself as today’s primarily a driving day, but don’t worry, there’s tons of scenic stops along the way. Think scenic seaside towns, sand dunes, spectacular lighthouses, and cheese! Yes, cheese! Because who isn’t fascinated by cheese?

Sure, California’s Highway One surely steals the show when it comes to coastal road trips, but Oregon’s coast is one for the bucket list as well! With quiet seaside coves, bustling beach towns, and secluded hideaways, you won’t want to miss the beauty that is Oregon.

A few recommended stops between Coos Bay and Cannon Beach, where we’ll be ending the drive today. If you’re not pressed on time you can easily spread these activities/stops out over two days.

Oregon Dunes National Recreation Area: Wind-sculpted sand dunes for days (literally, miles and miles and miles). This NRA is actually one of the largest expanses of temperate coastal sand dunes in the world, so yea, I wasn’t kidding when I said Oregon’s coastline is on par with California’s . You can even take a buggy or ATV tour of the dunes!
Haceta Head Lighthouse : The first of numerous lighthouses on our list, and this one just happens to be the brightest light on the Oregon coast and most photographed in the whole state. To say it’s simply stunning is a huge understatement.
Cape Perpetua: Don’t miss the Spouting Horn, an exploding salt water geyser, and Thor’s Well, a gaping pit with violent waves crashing in every direction that ultimately fall into a hole, just as weird and wonderful as it sounds.
Nye Beach: The perfect stop for a late lunch, depending on how much exploring/sand-duning you did earlier. This is also a great place to spend the night if you’ll be splitting the drive from Coos Bay to Cannon Beach into two days.
Yaquina Head Light: Being the tallest lighthouse on the Oregon Coast, you can’t miss this towering beauty
Devils Punchbowl State Reserve: This is a popular whale watching site and displays an intriguing geology. Also, as the name suggests, there’s a hollow rock formation shaped like a huge punch bowl. Better yet, go at sunset if you want to see something spectacular.
Tillamook Cheese Factory: Who could resist some fine, fine creamy cheese samples? Not I, that’s for sure! If you’re not familiar with the brand, Tillamook is a leading cheese provider in the area, who aims to connect farmers with everyday food lovers (hi!) with cheese and ice cream. Don’t miss the tour.
Cannon Beach: Phew, made it (finally)! HAYSTACK ROCK, enough said.

Finally, the last official stop on this Oregon coast road trip, the one and only Cannon Beach. Here at Cannon Beach, you’ll find the famous and ever-so-popular Haystack Rock (it’s a sight to be seen).

No matter where you stand, you’ll see it (I promise), as it towers 235 feet over the beach. If you can, plan your visit during low tide so you’re able to walk right up to Haystack Rock to search for sea creatures (crabs, sea anemone, mussels, and snails). Check here to see when the tide is at its lowest. Check out Pelican Brewing Company should you get hungry (the fish tacos were absolutely bomb).

Sleep: Hallmark Resort and Spa Cannon Beach or Surfsand Resort if you’re feeling fancy, or Hidden Villa Cottages for a less expensive room. Note that many of the hotels are quite expensive in Cannon Beach, so expect to pay at least $250 a night or so.

Thankfully, you’ve only got about an hour and a half drive west back to the city of Portland to complete this full Oregon road trip. Choose to drive back after your first night in Cannon Beach, or the morning after your second.

End: Portland → Phew, you made it back! Grab some Stumptown Coffee on your way home!

Are you visiting the state soon? What are you most excited about on this Oregon road trip itinerary!?

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Planning an epic Northern California road trip and looking for the best stops to make?! I’m here to show you all the highlights (think redwoods, deep blue lakes, and freshly shucked oysters)!

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The Complete Oregon Road Trip Itinerary (50 Stops & 4 Unique Routes!)

Post Summary: The Ultimate Oregon Road Trip Itinerary According To A PNW Local

Oregon. That magical spot in the corner of the United States where roaring waterfalls, epic coastlines, and mysteries in the forest all thrive next to each other.

It’s an incredible place that requires the guidance of PNW experts (that’s us!) to divulge all the best stops in the state. We’ve been exploring Oregon for years , so you can count on us to provide well-rounded tips to give you the best experience!

In this post, we’re sharing the most epic Oregon road trip route , including our favorite stops and custom trips of 2-weeks, 10-days, and 1-week to cater to your specific needs. Scroll all the way to the bottom to find a free Oregon road trip itinerary download , too!

Okay, enough talking, let’s get exploring!

The Ultimate Oregon Road Trip Itinerary (Exactly Where To Find The Best Spots!)

First of all, where is oregon.

Oregon is located in a region called the Pacific Northwest , which is located in the northwest corner of the contiguous United States.

Fixed between its northern neighbor, Washington , and its southern neighbor, Northern California , Oregon is a unique mix of giant redwood trees, raging waterfalls, high desert, and beautiful coastal wilderness.

It’s got a little bit of everything , which is why taking an Oregon road trip will probably be the most incredible thing you will do this year!

Here’s a little bit about Oregon to start…

Oregon is broken down into seven distinct regions, each with its own unique spin on Oregon culture and iconic destinations . Here’s a breakdown of what you might expect from each:

The Oregon Coast: 363 miles of accessible beaches, historic lighthouses, sea stacks, and gorgeous little Oregon beach towns .
Central Oregon: A High Desert escape including popular spots like Sisters, Bend, and Smith Rock State Park .
Eastern Oregon : Lonely vast desert with incredible geological features scattered across the area. Known for the Alvord Desert, Pendleton, and the Painted Hills.
Portland Region: The urban center for creatives, makers, and foodies. Known for its epic food culture, bridges, and accessibility to nature.
Mt. Hood & The Columbia River Gorge: Home to the highest mountain in Oregon (Mt Hood), and some of the most famous Oregon waterfalls like Multnomah Falls.
Southern Oregon: Home to Crater Lake National Park, this region also boasts adventurous caves, gorgeous forests, and hidden hot springs (Umpqua Hot Springs).
The Willamette Valley: Known for its amazing wine, tulips, and orchards, this farming community is a hub for a perfect weekend getaway.

Great…So Where Do I Start My Oregon Road Trip?

The easiest place to start your Oregon road trip is in Portland . This is the biggest city, where you will find the most options for car rentals, flights into the state ( Portland International Airport – PDX ), and stores to pick up any last-minute supplies.

Our Oregon road trip itinerary has you starting in Portland and heading east, but you can always fit the route to suit your own needs and desires! Keep scrolling to see all the stops so you can make your decision.

How Do I Get Around On My Oregon Road Trip?

Emily Mandagie driving the Oregon Coast Highway 101

The easiest way to get around on an Oregon trip is to drive in a car . It’s unreasonable to believe that you can fly from place to place. The biggest major airport is in Portland (PDX) and the rest are smaller local airports.

It’s easiest to get around Oregon in a car , and we highly suggest this mode of transportation! If you are hoping to do some camping along the way, we recommend checking out the company Outdoorsy to rent a campervan . It’s like having your transportation AND accommodations all in one place.

Outdoorsy does local recreational vehicle rentals (kind of like Airbnb but for cars!) so you can travel around Oregon in style with a cool vintage VW bus or cute teardrop trailer!

Where Do I Stay During My Oregon Road Trip?

The good thing about Oregon road trips is that they are completely customizable! You can stay at some of the coolest lodges and hotels in Oregon, explore backcountry roads for camping, or do a little mix of both!

Finding Epic Campsites in Oregon: There are so many amazing campsites in Oregon that the topic requires its own blog post! However, one of our most coveted tools for finding the best camping spots is through The Dyrt . The Dyrt is a campground finding app , and one of the best ones we’ve used! It’s got great reviews with photos, offline maps, road trip routing tools, and more! Our readers get to try it free for 30-days by using our code Mandagies !

Our favorite lodges & resorts in Oregon: Some amazing accommodations stand out among the others, and we think that some of these places deserve their own recognition! Here are some of our favorite lodges in Oregon that we recommend checking out!

FivePine Lodge – Sisters, OR (Central) Bay Point Landing – Coos Bay, OR (Southern Coast) Headlands Lodge – Pacific City, OR (Northern Coast) The Independence Hotel – Willamette Valley (Northwest/Central ORegon)

The Mega Oregon Road Trip Itinerary (All The Best Stop In Oregon)

This two week Oregon road trip will bring you to all the best spots!

Stop 1: Portland, Oregon

Before departing the city, spend some time visiting Portland’s coolest locations! Some of the most popular outdoor places to visit in the city include the Portland Rose Garden, Washington Park, the Pittock Mansion (with its view of the city!), and Forest Park.

Grab a bite to eat at one of the several food truck communities around town. Click here to locate all the food truck pods around Portland!

From here, make sure to stock up with snacks at your favorite grocery store, fill up with gas, and hit the road!

Stop 2: Columbia River Gorge Scenic Byway

Begin your Oregon road trip in Portland and head to Interstate 84 East to start your Columbia River Gorge Scenic Drive . This is a great start to any Oregon road trip itinerary for its iconic stops like Multnomah Falls, Latourell Falls, and Bridal Veil Falls.

If you want to go hiking in this area, consider Wahclella Falls Trail (only 1.9-miles long) or Munra Point Trail for incredible panoramic views.

To spend more time checking out cool waterfalls in Oregon , consider taking the Historic Columbia River Highway (that parallels I-84), which provides easy access to many of them. Don’t forget to drive a little farther than Hood River to check out Rowena Crest , that famous hairpin road!

Note: The Eagle Creek Fire of 2017 devastated much of this area, and hikes/waterfall trails are slowly opening after restoration efforts. Click here to be updated on real-time trail openings in the Columbia River Gorge .

Extra Stops Between Portland and Hood River:

Vista House – A museum, observatory, and rest stop
Bridge of the Gods – Many of the Pacific Crest Trail Hikers cross here!
Beacon Rock State Park (on the Washington side)
More than 25 Columbia River Gorge waterfalls to see!

Stop 3: Hood River, Oregon

Hood River, Oregon is the perfect place to stay after a day of planning fun things to do in the Columbia River Gorge ! Placed conveniently on the river’s edge, there is easy access to Mount Hood directly south, water activities like windsurfing , and Washington waterfalls right across the river in the Gifford-Pinchot National Forest to the north.

If you want a little more adventure, consider crossing the toll bridge ($2) to Washington and venturing on nearby trails to Falls Creek Falls , Panther Creek Falls, or Lower Lewis Falls.

Cool Places To Stay in Hood River, Oregon

Modern Townhome in White Salmon, WA (just across the river) MtAdamsView in Hood River (TONS of gorge and mountain views, sleeps 6) Best Western Plus in Hood River (great value, free breakfast)

Stop 4: Mount Hood

Route your Oregon road trip from the river’s edge to the mountains, more specifically to all the cool things to do in Mount Hood !

Watch a sunrise at Trillium Lake – one of the easiest lakes to reach on Mount Hood. On a clear day, you will be able to see the reflection of the picturesque Mount Hood beautifully framed in the distance! Other Mount Hood lakes include Frog Lake, Lost Lake, and Mirror Lake – each with their own unique reflection of the mountain.

If you are interested in discovering some cool hiking trails around Mout Hood, consider Ramona Falls trail. This gorgeous horsetail falls is hidden deep in the forest, but the payoff is huge once you see it with your own eyes. Care for a short waterfall hike for your Portland day trip? Consider Tamanawas Falls , an easy 3.3-mile trail with a gorgeous view!

Want to challenge yourself? Here are some other longer hikes in the Mount Hood area.

Tom Dick and Harry (9 miles out and back)
Bald Mountain (6 miles out and back)
McNeil Point Trail (9.6 miles out and back)

Stop 5: The Painted Hills

After stopping at Mount Hood (overnight or just for a day trip) take the 3.5-hour drive from Mount Hood to the Painted Hills to catch a gorgeous sunset in the Oregon desert.

The Painted Hills gets its name from the exposed layers of colorful soil that are revealed in the rolling hills of the John Day Fossil Beds . Make sure to stay on the boardwalks as you explore the Painted Hills. The hills are extremely fragile!

In the morning, return to the John Day Fossil Bed units and see the Painted Hills as the sun rises! This is a gorgeous time of day in the hills, and you’ll likely get it all to yourself in the early hours of the morning.

Need a place to sleep? Consider these nearby campgrounds (or click here to discover FREE campsites nearby too! )

Stop 6: Smith Rock State Park

From the Painted Hills through the Ochoco National Forest , take the 1.5-hour drive to Smith Rock State Park . Smith Rock is a hub for climbers , but there are several other things to do here, including hiking, biking, and taking photos!

To stretch your legs on this Oregon road trip, take the short but *very* steep Misery Ridge Trail . This 0.68-mile trail climbs 600 feet giving even the most experienced hiker a run for their money! The views at the top are worth it though, especially during sunrise or sunset!

Emily Mandagie biking in Sisters, Oregon - TheMandagies.com

Stop 7: Bend, Oregon

The city of Bend is an excellent stop on any good Oregon road trip! It’s an outdoor-loving town that connects Western Oregon and Eastern Oregon, making it a great pit stop to pick up last-minute gear, groceries, and maybe even tune ups for your car.

For a little relaxation from the road, grab a beer in town at any of the iconic stops on the Bend Ale Trail . If you are visiting in the summertime, floating the Deschutes River is a popular activity on a hot day. Make sure to bring your PFDs, water sandals, and a garbage bag!

In the morning, grab breakfast in Bend at The Sparrow Bakery, (their ocean rolls are famous!), and some to-go coffee at Spoken Moto and make some fun stops around Bend on your way south. Lava Island Falls and Lava River Cave are both easy and accessible places to see along your Oregon road trip route going out of town.

More adventures near Bend, Oregon

Hiking to Tumalo Falls (6.5 miles out-and-back)
Go backpacking in the Three Sisters Wilderness
Take a road trip detour on the Cascades Lake Highway

Read More: How to Spend 4 Days In Bend, Oregon

Eastern Oregon Road Trip Route - Leslie Gulch Stop

Oregon Road Trip Bonus Route – Eastern Oregon!

Psst…want to spend a lot more time in Eastern Oregon? Check out our Eastern Oregon Road Trip route right here !

From Bend, you have the option of extending your Oregon Road trip going east , or continue south and west towards the coast! Either option is great, it really just depends on how much time you have.

Stop 8: Oregon Waterfalls

The drive from Bend to Crater Lake National Park is pretty short, about 1.5 hours. This gives you plenty of time to make some fun stops along the way , most notably, to waterfalls in Oregon !

For longer Oregon waterfall hikes, make your way west on Highway 58 for a fun hike at Salt Creek Falls and Diamond Creek Falls . Continue your drive south and divert north on Highway 138 for a stop at Watson Falls before making your way to the Crater Lake North Entrance.

More Oregon Waterfalls Near The Area:

Proxy Falls (Highway 242 – North of Bend)
Chush Falls (Near Sisters, Oregon)
Dillon Falls
Benham Falls

Stop 9: Crater Lake National Park

Crater Lake National Park is one of the most iconic stops on an Oregon road trip, and the ONLY national park stop in the state. Spend sunset capturing the iconic Wizard Island on Crater Lake, and top it off by spending the night at the historic Crater Lake Lodge .

In the morning, spend an entire day hiking around Crater Lake on Watchman Peak Trail, Cleetwood Cove Trail, or Cloudcap Overlook.

At Crater Lake , you can spend the morning driving the Rim Drive , which takes about 2 hours to go all the way around. Hike to Plaikni Falls in the afternoon and in the evening watch the sunset at Garfield Peak or Sinnott Memorial Observation Station.

Emily Mandagie sitting in Hart Mountain Hot Springs in Eastern Oregon

Bonus Oregon Road Trip Stop: Oregon Hot Springs

Now, this is the part of your road trip route in Oregon where you can choose where you’d like to spend your time! You can opt to continue driving east to explore some of the famous Eastern Oregon hot springs .

If you decided to check out some hot springs in Oregon , we highly suggest booking an overnight stay (Summer Lakes Hot Springs and Crystal Crane have lodging available!) or bringing your camping gear to find some free camping nearby .

Here are some Oregon hot springs you should be checking out on this leg of your Oregon road trip itinerary:

Crystal Crane Hot Springs – Hot spring pond and private soaking tubs
Summer Lakes Hot Springs – Communal bathhouse
Hart Mountain Hot Springs – Structured underground pool and open springs, both natural
Have an extra day? Drive farther east and check out Alvord Hot Springs , and Willow Creek Hot Springs !

Stop 10: Umpqua National Forest

Another iconic destination on your Oregon road trip is an adventure in Umpqua National Forest . You’ve probably seen pictures of those cliffside hot springs pools, or the rushing waterfall flanked by towering basalt cliffs. Well, these places are Umpqua Hot Springs and Toketee Falls !

Both places are easy to reach, each with a short hike to the final destination. Come with a national forest pass to hang in your car’s rearview mirror. You can pick one up at the Diamond Lake Ranger Station nearby if you need one. See the difference between Pacific Northwest forest passes here to find the correct one.

Leave No Trace Notes: Umpqua Hot Springs is notorious for garbage . Please pack out your trash, and consider taking other garbage with you, too. Hiking to the base of Toketee Falls is prohibited , no matter how many pictures you see of people doing so. It is possible to get cited for climbing down to the bottom, so don’t risk it!

Best Beaches on the Southern Oregon Coast - Natural Bridges

Stop 11: Southern Oregon Coast

Finally, the first ocean stop on your Oregon road trip!

The Southern Oregon Coast is arguably the most beautiful area of an Oregon road trip. If you love seaside cliffs, hidden coves, and gorgeous beaches, this is the place for you!

Spend some time exploring the 12 miles of protected coastline at Samuel H. Boardman Scenic Corridor . This part of your road trip in Oregon will take an entire day, between stops, viewpoints, and even a hike to a place called Secret Beach .

Finally, end your day in Gold Beach for the evening. Here, you can find tons of amenities, hotels, and beach rentals for a quiet and relaxing evening. Make sure to stop at our favorite beach, Myers Creek Beach to enjoy a beautiful Oregon coast picnic to end the day!

Read More: The 25 best beaches in Oregon (From North to South!)

Stop 12: Central Oregon Coast

Central Oregon is full of adventurous destinations and unique curiosities. If you like thrills, try renting an ATV to ride across the Oregon Dunes, stretching 40 miles across the coastline.

You can also check out incredible places like Cape Perpetua , which is filled with churning coves, sea spouts, and lots of tide pools along the Oregon Coast .

Devil’s Punchbowl State Natural Area is another great place to explore, with a giant sea cave and surfing opportunities!

In the evening, splurge to go glamping and one of Coos Bay’s coolest spots – Bay Point Landing ! This luxury camping resort has plenty of pull-in sites for RVs and trailers. You can also rent a standalone cabin , airstream , or renovated RV of your own to enjoy upscale camping. The grounds have amenities like a pool, lounge room, upscale bathrooms, and a cute camp store.

Downtown Eugene 20x21 Mural Project - TheMandagies.com

Stop 13: Eugene, Oregon

If you wanted to go inland to explore the Cascade Mountains, this is the part of your Oregon road trip to make that decision! Drive away from the Oregon coast to go inland to Eugene, Oregon, and explore this upbeat college town.

But before leaving the coast, consider stopping by Heceta Head Lighthouse and Cape Perpetua for one last adventure by the water. The lighthouse can be seen up close with a short hike, which is incredible at sunrise and sunset!

Cape Perpetua is best explored during low tide, where you can access the many tide pools and curiosities that dot the shore. If you do come during high tide, don’t fret! You can see the waves push up through Thor’s Well for a dramatic display, and the Devil’s Churn to watch the waves crash around this small cove.

Stop 14: Willamette National Forest

Heading inland from Eugene, there are a ton of beautiful places to see in the Willamette National Forest . The first stop is Terwilliger Hot Springs (often called Cougar Hot Springs) for a lovely natural soak. Keep driving to choose a waterfall adventure – Proxy Falls , Sahalie and Koosah Falls , The Blue Pool , and Tamolitch Falls .

You’ll want to spend at least a full day in this area (or even go camping overnight!) because the trails here are packed with adventure! Keep driving on Highway 126 as it continues on Highway 22 north to Silver Falls State Park and Salem, Oregon to continue on your epic Oregon road trip.

Stop 15: Salem and The Willamette Valley

If you like good food, you’re going to love this stop on your Oregon road trip. The Willamette Valley is full of wineries, farms, and beautiful vineyards! There are lots of options to enjoy farm-to-table dinners, wine tastings, and all-day experiences. Consider staying nearby at the Independence Hotel .

For a little adventure, head to Silver Falls State Park where you can hike the Trail of Ten Falls . This Oregon hike is exactly what its name entails – ten beautiful falls in an 8.7-mile trail. Come enjoy this condensed version of many iconic Oregon waterfalls all in one place!

Stop 16: Northern Oregon Coast

Refueling in Salem, it’s time to get back to the coast! The final stops on your Oregon road trip include classic North Oregon Coast stops and beautiful Oregon beach towns , hikes, and plenty of dreamy overlooks.

Beginning in Cape Kiwanda , spend the day hiking up the sand dunes to watch the dory boats dock onshore and paragliders sail down to the beach. Make sure to stop and eat lunch at Pelican Brewing . They have incredible beer and pub food, with an outdoor patio overlooking Pacific City’s own Haystack Rock.

Continuing north to another iconic “Haystack Rock” (arguably the most popular one too) Cannon Beach is the best place to grab a coffee and take a walk along the beach. During low tide, you can get close to the rock and spot puffins in their natural habitat!

If you want a little more adventure in your day, drive up to Ecola State Park to hike Crescent Beach Trail , the trail to Indian Sands, or Tillamook Rock Lighthouse Viewpoint. These lush Oregon Coast hikes are sure to leave you breathless!

Stay either at the Headlands Lodge in Pacific City , Oregon Coast Modern Cabin in Manzanita , or affordable hotels in Cannon Beach !

Peter Iredale Shipwrek at Fort Stevens State Park

Stop 17: Finish Your Oregon Road Trip Back to Portland, Oregon

On your way back to Portland to finish your Oregon road trip, you can take the short way on Highway 26, or the long way through Astoria, Oregon, and heading back to the city on Highway 30.

The detour through Astoria won’t disappoint! Filled with great restaurants, antique and vintage shops, and lots of history, it’s a perfect final stop on the Oregon coast road trip section of your drive.

For outdoorsy activities, stop by Fort Steven’s State Park to check out the historic military installation, as well as the famous Peter Iredale shipwreck . For hiking, stay close to town and check out the Cathedral Tree Trail and the Astoria Column .

And you’ve done it! You’ve completed the coolest Oregon road trip to see all the best highlights, hikes, and iconic locations in the state.

Oregon Road Trip Itinerary Examples

Below, we’re sharing some Oregon road trip itinerary examples to help you customize it exactly to fit your needs. For even more resources, we created this road trip itinerary in Oregon to print out and take on your journey!

(We’re running some email maintenance – this download will be back soon!)

Two Week Oregon Road Trip

See the detailed breakdown of our two-week Oregon road trip itinerary above!

10 Day Oregon Road Trip

You can see a lot with 10 days in Oregon! This route is a compressed version of our two-week road trip, with just a little less time in each spot but plenty of stops for an epic and interesting route!

Day 1: Portland to Hood River
Day 2: Hood River to Bend, Oregon
Day 3: Bend, Oregon to Crater Lake National Park
Day 4: Crater Lake to Umpqua National Forest
Day 5: Umpqua National Forest to Samuel H. Boardman
Day 6: Samuel H. Boardman to Coos Bay
Day 7: Coos Bay to Eugene, Oregon
Day 8: Eugene, Oregon to Salem, Oregon
Day 9: Salem, Oregon to Cannon Beach
Day 10: Cannon Beach to Portland, Oregon

One Week Oregon Road Trip

One week for an Oregon road trip will introduce you to Oregon’s vast and diverse landscape! From Crater Lake to Bend, Coos Bay to Cannon Beach, this route will bring you to some of the best of Oregon photography locations.

Day 1: Portland to Hood River
Day 2: Hood River to Bend, Oregon
Day 3: Bend, Oregon to Crater Lake National Park
Day 4: Crater Lake to Samuel H. Boardman
Day 5: Samuel H. Boardman to Coos Bay
Day 6: Coos Bay to Cannon Beach
Day 7: Cannon Beach to Portland, OR

5 Day Oregon Road Trip

With 5 days in Oregon, you can see the highlights! This quick trip averages about 3-4 hours of driving per day, and takes you through mountains, by waterfalls, and meets up with some of the most scenic views along the Oregon Coast.

Day 1: Portland to Bend
Day 2: Bend to Eugene
Day 3: Eugene to Samuel H. Boardman
Day 4: Samuel H. Boardman to Yachats
Day 5: Yachats to Portland

Have you ever experienced an Oregon road trip? What Oregon itinerary is your favorite? Tell us in the comments below!

Amazing! I know nothing about traveling all over the country, what a wonderful looking place to explore.

I’m really glad you liked our Oregon road trip route! I hope you et a change to travel across this beautiful state!

How to Plan an Incredible Oregon Road Trip (14 Days)

Looking to plan an amazing Oregon Road Trip? You’re in the right place. We live in Portland, and spend a big chunk of our summers on the road exploring our adopted home state of Oregon. We’re here to use our experiences around Oregon to help you plan your own amazing Oregon adventure.

We’re going to go over a perfect road trip itinerary that takes you to many of our favorite places in Oregon over 14 days, which is based on our own experiences exploring the state.

Have more or less time than that? Have no fear, we’ve got ideas on how to structure a trip with more and less time below the main itinerary, and you can use the details in the main itinerary to help you plan out your trip.

We were lucky enough to spend two whole months on a road trip around Oregon a few summers ago after we had to scrap our international travel plans, and it taught us an important lesson: you don’t need to fly halfway around the world to find wild and beautiful places – sometimes they’re right in your backyard the whole time .

It also cemented our belief that Oregon was the place we wanted to put down roots and create a home base after years of living on the road.

Fast forward a couple of years, and we decided to make our forever home in Portland, Oregon, and that initial time exploring Oregon was a huge part of why we ultimately ended up making that decision.

Oregon has it all – the coast, the mountains, the desert, a truly unbelievable number of amazing waterfalls, and more.

In this complete guide to planning your Oregon road trip itinerary, we’re going to give you the logistics you need to know – when to visit and our recommended route – along with a mini guide to each place on the itinerary.

That mini guide will have information like what to do and where to stay – all based on our own experiences exploring Oregon – along with links to more in-depth content we’ve written on the destination.

In each “where to stay” section, we’ll give you options for camping (which is what we usually do) and not camping, which we recognize is what the vast majority of people prefer.

Finally, at the end, we’ll give you some ideas on how to shorten or lengthen the itinerary to fit your particular trip.

Sound good to you? This guide is super detailed, full of our tips and favorite places based on our extensive experience exploring Oregon, which means it’s LONG. Strap yourself in, grab a cup of coffee (or beer or wine, no judgment here), and let’s get to exploring Oregon!

Disclaimer: Some of the links in this post, like hotel and vacation rental links, are affiliate links, meaning at no additional cost to you we make a little bit of money if you click through and book. That being said, we would absolutely never recommend something to you that we don’t stand behind 100%.

A Quick (and Oversimplified) Oregon Geography Lesson

Before we get into the road trip itinerary, let’s quickly talk about Oregon’s geography, and what it means for your trip.

First of all, Oregon is a lot bigger than you probably think. It’s the 9th largest state in the country by square mileage, which is a fact that blew my mind. Driving between places can take several hours, if not more.

Why do we bring this up? Because it has one major implication for your trip.

Unless you want to spend full days of your trip driving without stopping to see the scenery, you’re not going to be able to see the entire state .

Fear not – we have a strong perspective on where you should focus your time if it’s your first trip to Oregon. Which means we need to talk about Oregon’s geography.

Oregon is a very diverse state when it comes to landscapes, which is part of why we love it. It’s home to rocky coastline, wide sandy beaches, rolling hills and lush valleys, moist rainforests, towering snowy peaks, and even the high desert.

When you think about Oregon’s geography, we’d cut the state roughly into quadrants, with Eugene as the center point in the state.

If it’s your first time in Oregon, you’re going to want to focus on the northwest quadrant, almost exclusively . The exception might be Crater Lake National Park, which we have a whole section on below to help you figure out where to fit it in.

If you start to try fitting in places all over the state, you’re going to spend entire days driving long distances, which we don’t really think is the best experience. For reference, it takes three and a half hours to go from Newport on the Oregon Coast over to Bend (without traffic). Then, it’s another two hours to the Painted Hills from Bend. And a full four hours back to Portland from there.

In this itinerary, Bend is the furthest east you’ll go. It’s just not feasible to get to every corner of the state, especially with limited time.

If you happen to have an extra week (lucky you!), that’s when we’d add the Painted Hills and Wallowa Mountains, and some of the other spots in eastern Oregon. Or the southern Oregon coast, which is much more rugged and wild than the northern coast that you’ll cover in this itinerary.

How Many Days Do You Need for this Road Trip?

We really, really think that to do a full road trip around Oregon that includes both the northern coast and Bend, you need a full two weeks (14 days) . Otherwise, you’ll spend way too much time driving, and not enough time out exploring.

Which is exactly how we’ve written the road trip below.

If you have 7-10 days , we’d do a more focused road trip that follows a figure-8 with Portland at the center. Head east to the Columbia River Gorge, Hood River, and Mount Hood, then come back through Portland and head out to the Oregon Coast for a few nights, focusing on the stretch from Astoria to Tillamook. Here’s a map .

If you do have less time, we have example itineraries for 7 and 10 day road trips below the main itinerary to help you organize your time.

The Best Time to Plan a Road Trip in Oregon

This is a very, very important section in this guide, which is why it’s the first thing we’re talking about.

If you are interested in hiking in the Cascades – specifically near Mount Hood or Bend – your trip will need to be sometime between July and mid-October .

Otherwise, high elevation hiking trails will be covered in snow, and some roads and sections of the parks will be closed.

The exact timing depends on the year, precipitation, and spring temperatures (among other factors), but you will be most safe with a trip in August or September .

The best time to plan this road trip is going to be July, August, and September . That’s when roads are open, trails are largely snow-free, and you’ll be able to see everything you want to see.

During the summer and early fall, mountain passes and hiking trails are clear of snow, days are warm and sunny, the sun rises before 6:00 am and sets after 9:30 pm, and it’s an all around spectacular time to be in Oregon.

The downside is that, in recent years, Oregon has been ravaged by forest fires during the summer, bringing a thick smoke that makes it really unhealthy and unpleasant to be outside. It’s hard to predict, but it’s something to be aware of if you’re planning a trip in the summer.

Early fall is another great time to visit Oregon. The weather is, for the most part, still great (though it’s a little more unpredictable than summer).

As you get into October, things start to cool off and snow can begin to show up in some of the passes through the Cascades (the McKenzie River Scenic Byway, for example), which can make travel a bit more difficult.

Spring is gray and wet, though late spring (think Memorial Day into June) is a cool time to visit Oregon because of the blooming rhododendrons and roses. The weather isn’t going to be the best, but you’ll probably get a few nice, clear days over the course of your trip.

In the spring, hiking trails at elevation – like around Mount Hood and Bend – are still going to be closed. If you’re into hiking, we’d definitely recommend waiting until later in the summer .

Winter isn’t a great time to do this road trip, if we’re being totally honest. The Cascades are blanketed in snow, which means you won’t get much of a taste of the mountains in Oregon (though you can get some skiing in at Mount Bachelor!) and the mountain passes are harder to navigate, often closing for days at a time due to winter storms.

The upside of visiting in the winter is that the waterfalls in Oregon are WILD when it’s raining.

If you’re visiting in the winter, we’d stick to the areas west of the mountains and do the Columbia River Gorge, Hood River, Silver Falls State Park, and the Oregon Coast . For what it’s worth, we’ve done the Oregon Coast multiple times in the winter, and it’s very moody (and wet).

Here’s a map of what a winter road trip in Oregon might look like.

Where to Start and End Your Road Trip

This one is easy – Portland!

Portland is not really central in terms of the state – it’s up in the northwest corner – but it is central to some of Oregon’s best sights (the coast, Mount Hood, the Columbia River Gorge, etc etc) AND it’s the best airport in the state (dare we say country?).

Unless you live somewhere in Oregon or you’re driving up from California, the answer is Portland .

The exception is if you have 10 days in Oregon and follow our road trip itinerary below. In that scenario, we’d recommend flying into Portland, and out of Bend (Redmond Municipal Airport, RDM) to save time on driving back to Portland just to catch a flight.

Flights out of Bend will be more expensive and involve connecting through Portland or Seattle, but it’ll save you four hours of driving.

Where to Fly in and Out of?

The best option, with the most flights coming in and going out, is going to be our home airport – Portland International Airport (PDX) .

Having lived in both Seattle and San Francisco, PDX is amazing when you compare it to those airports.

It’s relatively well organized (as well organized as an airport can really be), and it’s clean, has good local food and drink options, and the security lines are never “oh no am I going to miss my flight?” long.

There are a couple of smaller airports in Oregon that could work, but will likely be more expensive and have fewer flight options. Those would be places like Eugene (EUG) and Bend / Redmond (RDM) .

Chances are, PDX is going to be the best choice for about 99% of people. Plus, there are more rental car options!

Do You Need to Rent a Car?

It probably goes without saying that you will need a car to do this road trip. If you’re coming from out of state, that probably means renting a car when you arrive.

One thing we’d recommend is that you avoid having your rental car when you’re in the city of Portland .

We’ve organized the itinerary below to have Portland at the end, and we’d strongly recommend that you drop your car off at the airport when you roll into Portland, and spend your day or two in town carless.

Another cool option would be renting a campervan for this road trip! On our six week road trip around Oregon in 2020 – the one that made us fall in love with the state and eventually move here – we lived out of our converted Honda Odyssey.

We love the flexibility of van living, though it certainly isn’t nearly as sexy as it looks in all of those pictures on Instagram.

We have a few favorite campgrounds in Oregon that we’ll give you in the itinerary below that are a once-in-a-lifetime experience (looking at you, Trillium).

One thing we’ve been DYING to do is rent an Escape Campervan . If you’re looking to experience the whole camping thing, but don’t want to sleep in a tent (to be clear, we’re all for tent camping), then a campervan might be for you!

Escape’s vans are all hand-painted, have full kitchens, and would be a lovely way to experience Oregon.

Escape has an office in Portland , which is where you’d pick up and drop off your van.

The Route for This Road Trip

With that in mind, here’s a summary of the 14 day road trip we’ll cover in detail below.

Day 1: Astoria

Day 2: cannon beach, days 3-4: tillamook & the three capes scenic route, day 5: newport, cape perpetua, & heceta head lighthouse, day 6: drive the mckenzie river scenic byway to bend, days 7-8: bend (and the cascade lakes scenic byway).

Day 9: Smith Rock State Park
Days 10-11: Mount Hood (Government Camp)

Days 12-13: Hood River and the Columbia River Gorge

Day 14: Explore Portland

Here’s a map of that route.

We think this itinerary is a good blend of scenic drives (the Oregon Coast and the McKenzie River Scenic Byway are two of our favorites), cool towns (Astoria, Hood River, and Bend), and great outdoor adventures.

Which is basically everything we love about Oregon, packed into two weeks (minus some of the further out spots that don’t make sense here).

Like we said, you can’t fit it all into one road trip. But we’ve done our best to include the highlights in hopes that you’ll fall in love with Oregon and come back a second (and third) time to explore more.

Of course, that’s just the base itinerary that we’d recommend. The exact route you take is going to depend on your particular interests, what time of year you’re visiting, and more factors than we can possibly take into account here.

We have ideas for shorter and longer itineraries below the main itinerary if you have more or less time.

We’ll do our best to give you all the information you need to plan YOUR road trip in Oregon, but if we miss something or you have more questions, leave us a comment below and we’ll do our best to either answer your question, or point you to someone who can.

Exactly How to Plan an Amazing Oregon Road Trip Itinerary

Now that we’ve covered the logistics you need to know to really plan your trip, let’s get into the itinerary itself!

There are a couple of principles that we’re going to follow as we take you through our perfect version of a road trip in Oregon.

We think you should see the mountains and the coast . Both are spectacular, and part of the reason we love Oregon is that you can go from the mountains to the coast in about two hours, give or take. It’s magical.
Oregon is big, and you don’t want to spend the entire time driving . We’re going to try and make sure you’re only driving a maximum of four hours between destinations, which means more time exploring, less time driving.
There are too many places to see in one trip . Instead of trying to fit every single place into one road trip, we think you should focus so that you aren’t just rolling into a place in the late afternoon, and leaving the next morning. This, of course, means that you’re probably not going to be able to fit every single place into your itinerary. And that’s okay! You can always come back. In this itinerary, we’re focusing on the western half of the state, which is NOT to say there aren’t amazing things to see east of the Cascades.

With those principles in mind, we’ve created this 14 day Oregon itinerary so that you can almost literally copy and paste it for your trip if that’s what you want.

Or, you can use bits and pieces of it to cobble together your own version of the road trip. Whatever works best for you!

Drive Time / Distance from Portland International Airport to Astoria: 2 hours / 95 miles

Where to Stay in Astoria: You want to stay centrally so you can walk to the attractions downtown. We stayed at Norblad on our last trip, and liked it (nice location, stylish rooms, comfy beds).

Astoria is a fitting first stop on this itinerary, because in many ways, it’s where the state of Oregon as we know it today began. Lewis and Clark Historical Park, which is just south of the city center, is near the location where Lewis and Clark made camp for three months, having completed their mission to find the Pacific Ocean.

Now, you might be thinking that Lewis and Clark, who had completed their ultimate goal after a significant chunk of time spent struggling west from St. Louis, might have been celebrating with their feet up.

But their arrival and stay happened to be smack dab in the middle of winter – from December through February – so rather than celebrating with the long, warm days of an Oregon summer, they were treated to constant drizzle and less than eight hours of sunlight. FUN.

Anyway, Astoria is meaningful in many ways, from the early 19th Century and Lewis and Clark’s antics, to the time when John Jacob Astor tried to make Astoria the New York City of the west (he almost had it!).

Today, it sits at the northwestern corner of Oregon, and is home to what has to be the highest number of breweries per capita in the country (there’s four or five, and Astoria is tiny), and filming locations for some of the iconic films of the 90’s (the Goonies and Kindergarten Cop, among others).

What to Do in Astoria

Here are some of our favorite things to do in Astoria.

Lewis and Clark National Historical Park : Like we mentioned, Lewis and Clark National Historical Park is near the site of Fort Clatsop, which is where they set up camp for three miserable months before heading home to report back to Jefferson. There’s a model of Fort Clatsop here, a bunch of fun information on what life was like on that expedition (and some very charismatic rangers eager to share anecdotes like the one above), and a hike that connects the fort with the coast, a route that they covered many times. However, the hike isn’t really worth too much of your time – it’s 6.5 miles one way out to the coast – we’d do the first mile or so, enjoying the ferny forests of sitka spruce trees before heading back.

The Astoria Column : The Astoria Column is perched up on the hill above town with a commanding view out over the Columbia River and the famous Astoria-Megler Bridge – that’s the green bridge crossing the river to the Washington side. The Column is an interesting piece of art, because it is wrapped in the story of Astoria. It’s hard to see the artwork when you’re standing at the base looking up at it, but there’s a digital re-creation with labels that is helpful to understand exactly what you’re viewing. You can climb to the top of the column for an even more impressive view of the river. It costs $5 to park in the lot at the Column, or you can park at the base of the hill in town (roughly here ) and hike the Cathedral Tree Trail up for free.

Fort Stevens State Park : This is the northwest corner of Oregon, and also – fun fact – the site of the only attack on a military base in the contiguous United States since the War of 1812 (the Japanese shelled it a few times in 1942). It’s a State Park, though it was a military base through the early 20th Century. Today, the bunkers are one of the main draws here, and are particularly interesting when there are rangers and volunteers out there to tell you stories about the local history (which is usually on weekends in the summer). It’s worth driving out to the coast and hitting the wreck of the Peter Iredale , a shipwreck on a wide sandy beach, and Clatsop Spit at Lot C ( here on Google Maps) where you can walk out along the rocks on the Pacific.

The Breweries: Two of Oregon’s best breweries are up in Astoria – Buoy Beer Co and Fort George Brewing – and are basically a must-stop for any beer aficionados who find themselves in the state’s northwest corner. They each have a taproom within walking distance of the main drag, and both have food menus and extensive taplists, with many beers you’re not going to find outside of the taproom. In addition, there are a few smaller breweries (like Fortune and Glory Cider Company – technically not a brewery, I guess). Across the street from them is Bridge & Tunnel Bottleshop & Taproom , the best beer bar in Astoria (and a good place to try multiple beers from different breweries).

Drive Time / Distance from Astoria to Cannon Beach: 40 minutes / 25 miles

Where to Stay in Cannon Beach: For Cannon Beach, you have two choices – on the beach (more expensive, nice experience) or a few blocks away from the beach (cheaper, less romantic). We’ve stayed at the Inn at Haystack Rock twice , which falls in the latter category and is nice enough (but probably needs a bit of a facelift in the next couple of years).

Cannon Beach is one of the most popular day trips from Portland , because it’s a mere 90 minutes from downtown Portland. As a result, the area can feel unbearably overcrowded on summer weekends, as Portlanders (us included) flock to the coast to escape the inland heat.

However, on a weekday or early in the morning and later in the evening, Cannon Beach is a lovely place to spend some time.

We recently went out to Cannon Beach – our first beach foray with our dog, Lupine – midweek in January, and we were basically the only people on the hiking trail in Ecola State Park. It was wet and muddy, yes, but it was so peaceful.

The highlights in Cannon Beach are actually the state parks that border the town on the north and south end, Ecola State Park and Oswald West State Park .

Sure, Cannon Beach – the town AND the beach – is nice, and you should definitely do a sunset walk on the beach. But definitely don’t miss the nearby state parks.

What to Do in Cannon Beach

Here are some Cannon Beach highlights that you really shouldn’t miss.

Haystack Rock: It’s cliche, but Haystack Rock really is an impressive sight, especially if you’re not used to the towering sea stacks that you find up and down the Oregon and Washington coast. In fact, we’d argue that Haystack Rock is up near the top of the list of tourist attractions in Oregon, somewhere below Multnomah Falls and above Powell’s Books in Portland. It’s a huge sea stack, rising 235 feet out of the surf to tower over the beach and surrounding community. It’s particularly spectacular at low tide, when you get some cool reflections in the wet sand. On our first trip to Cannon Beach, we witnessed a pair of Bald Eagles raiding the resident puffin colony for their eggs! It was quite the drama, and there are rangers on the beach in the summer who talk about the puffins and the attempts to keep them alive.

Ecola State Park: Ecola State Park was closed for years and years until very recently, when it was reopened to the public. As you drive in on the windy, tree-lined road, it’s easy to see why a couple of bad storms put the park out of commission for a couple of years. This park is one of the most popular destinations on the Oregon Coast, so it’s likely to be busy if you’re here in the summer or on a weekend. Get there early to get a parking spot in the relatively small lots! There are two things not to miss in Ecola State Park, we think.

The first is Crescent Beach , which is a short hike accessed either from the main parking lot, or by walking into the park from Cannon Beach. From the main lot, which you should visit whether you do the hike or not for the views, it’s a short downhill hike that winds through the ferny forest before an aggressive descent down to the beach. The beach is best at low tide, when it’s wide and sandy and littered with driftwood and sea stacks. Basically, everything you could possibly want in a Pacific Northwest beach.
The second is Indian Beach . There’s a parking lot right at Indian Beach that fills up early because it’s a popular surfing destination. You can also hike out to Indian Beach from the main parking lot in the park, which is worth doing for the coastal views along the way.

Hiking in Oswald West State Park: This is the other Oregon state park we referenced above, and it’s equally worthwhile. There are three hikes here to focus your time on. First is the hike to the top of Neahkahnie Mountain , which is an aggressive ascent up switchbacks to a viewpoint where you can see miles and miles of coastline to the south. Second is the hike out to Cape Falcon , which navigates out to the cape on the north side of Short Sand Beach, where you’ll have excellent views back towards the beach. Be aware that this hike is almost always extremely muddy. Seriously, do not underestimate the mud, even in the early summer. Third is the hike – though it’s more of a leisurely walk – out to Short Sand Beach , which is a wide sandy beach (at low tide, anyway) that is very popular with surfers.

Drive Time / Distance from Cannon Beach to Tillamook: 55 minutes / 40 miles

Where to Stay in Tillamook: Tillamook itself isn’t really the nicest city, but there are some nice places to stay up and down the coast from town. We stayed in one of the tiny homes at Sheltered Nook , which is just north of the city, and really liked it (full kitchens, nice outdoor seating).

Everyone who has spent any significant amount of time in the Pacific Northwest knows Tillamook because of the cheese, ice cream, sour cream, or some other dairy product that every supermarket carries.

And while you’re in Tillamook, you should definitely visit their factory for a tasty, educational experience.

However, Tillamook is also home to the Three Capes Scenic Route, which is well worth a half day of your time to explore as well.

What to Do Around Tillamook

Here are three things not to miss when you’re in Tillamook.

The Three Capes Scenic Route: Like we mentioned above, this is probably the premier thing to do near Tillamook. The Three Capes Scenic Route covers a 30 mile stretch of the Oregon Coast from Cape Meares to Cape Kiwanda (Cape Lookout is between them, and rounds out the “Three Capes”) where you’ll have great coastal views around every bend in the road. If you’re following this itinerary as we’ve laid it out, you’ll be heading north to south.

Cape Meares is your first stop, and there are two things to check out. First is the Cape Meares Lighthouse, which is the shortest lighthouse on the Oregon Coast. However, it has an impressive lens that was installed in 1890. The second thing not to miss is the Octopus Tree (it’s a weird looking tree with eight branches, hence the name) and the viewpoint right past it that looks out over the beaches to the south, including Short Beach. It’s a short walk from the main parking lot.
Cape Lookout is your next stop, and is our personal favorite of the three. The highlight, by far, is the hike out to Cape Lookout . It’s a relatively easy hike that hugs the cape, which narrows as you get further and further out onto it before the trail ends at its western tip, where the views are amazing and you can hear the seals frolicking on the rocks below. It’s also a good place for whale watching in spring, because it’s about as close to the migrating mammals as you can get.
Cape Kiwanda is the last of the three capes, and it’s a little different. It’s very popular with surfers, and you can drive out onto the beach, which means it’s a slightly different crowd that includes fishermen and boaters. From the parking lot, the main attraction is up and to the right of the beach, where you can hike up onto the cape for some great views in both directions. You’ll be hiking up in deep sand, so it’s harder than it looks. Make sure to catch the hang gliders, if they’re out, who use the northern end of the cape as a jumping off point.

Tillamook Cheese Factory: The Tillamook Cheese Factory is legendary. Not only is there a cool educational experience where you can see how they make the cheese, but there are some truly great food options, including a huge ice cream scoop shop. If you’ve never had their ice cream before, it’s incredibly creamy. That’s their whole thing. The chocolate peanut butter swirl is Alysha’s favorite, with thick, creamy swirls of peanut butter tucked into their chocolate ice cream.They also have a retail store here, where you can buy all of their cheeses, including some of their hard-to-find reserve varieties, along with a selection of other local products. If they have them, do not miss their cheese curds, which are only available at the factory and are incredible (we’d never had them before we bought them a few years ago and fried them up post-hike over our camp stove – incredible).

More Cheese: There’s actually a second cheese destination down the road – Blue Heron French Cheese Co – though we weren’t nearly as impressed with the presentation. The cheese – which leans towards French style – is really good, though.

Hiking in Lincoln City: Technically this isn’t Tillamook – it’s 30-45 minutes south – but we’re including it here because two of our favorite hikes on the Oregon Coast are in and around the sleepy coastal community of Lincoln City. The first is Cascade Head , which is maintained by the Nature Conservancy (no dogs allowed). It’s a great hike that climbs through the forest and emerges onto a (very windy) bluff over the ocean, which you can climb up for some great coastal views. It’s windy as you get out onto the coast, so be prepared. The second is God’s Thumb , which is a short hike from the north end of Lincoln City that takes you out to a point, which looks out over the Oregon Coast both north and south. Along the loop, you’ll pass the Knoll, where you’ll have a great view of the neverending sandy beach that stretches out to the south.

Drive Time / Distance from Tillamook to Newport: 1 hour 30 minutes / 70 miles

Where to Stay in Newport: We haven’t stayed there ourselves yet, but the Inn at Nye Beach has been on our list for years now.

Newport is the biggest city on the central Oregon Coast, and has the best selection of places to stay, restaurants, and other amenities like grocery stores before you get into the more rural southern Oregon Coast.

The structure for today is essentially using Newport as a home base to continue your road trip south along the coast past Newport (which is one of our favorite stretches of the Oregon Coast) and then returning to Newport for the night to set yourself up for a long drive the next day.

Just south of Newport, the coast starts its transformation from the very developed, very tourist-friendly northern Oregon Coast to the more rugged southern Oregon Coast, which is rockier, less-traveled, and offers a little more peace and quiet than places like Cannon Beach and Seaside.

From Newport, you can hit one of the most scenic drives on the coast – the area around Cape Perpetua and Heceta Head – before returning to Newport for the night to eat some fresh seafood and check out one of the many beaches in town.

What to Do Around Newport

Here are our favorite things to do in and around Newport.

Devil’s Churn: A short stop where you’ll hike down to an overlook with a view of an inlet that is partially covered at the end. Which means at high tide, if you’re lucky, the waves coming in will meet the waves going out and create an explosion of water.

Cape Perpetua: The view from the top of Cape Perpetua is one of our favorite views on the coast, and it reminds us a lot of Big Sur down on the California Coast (at least on a sunny day). You can hike from the lower road up to the top , which is a nice workout, but you can also just drive to the top (which we didn’t know until we got up there, sweaty and huffing and puffing). There really isn’t a reason to do the hike other than a workout – there aren’t really any additional views you get by hiking.

Heceta Head Lighthouse: This is one of the most beautiful lighthouses on the coast, and it’s easily accessible from the parking lot. It sits on a 1,000 foot headland that towers over the Pacific, and they have tours of the lighthouse, a charming B&B in the old light keeper’s home, and tidepools and trails to explore. You can hike out to Hobbit Beach from the lighthouse, which is a nice little trail that follows the coast to a sandy beach.

Sea Lion Caves: We drove past this place on our first trip, saw a line out the door of a tiny little touristy-looking hut, and said “look at those suckers!” Then we learned what it actually was later on from some Oregonians, and were at least a little bit disappointed that we didn’t stop in. If you want to see sea lions, this is the place to do it. That hut sits over an elevator that takes you down hundreds of feet to the water level, where there’s a sea cave – America’s largest, in fact – filled to the brim with barking sea lions. Skeptical? Here’s the webcam where you can see for yourself. They’re open 9:00 am – 4:00 pm 363 days a year, and it costs $16 for adults, $10 for kids (under 4 are free!), making it a little bit pricey.

Exploring Newport: Newport is probably best known for its world-class aquarium – the Oregon Coast Aquarium – which we stopped at and immediately turned around when we saw the flood of small children (it would be a good family activity, though!). There are two lighthouses in town, and the Yaquina Head Lighthouse is at the northern end of town, and is well worth a stop (the Yaquina Bay Lighthouse is less impressive). Definitely head down to the charming Historic Bayfront for dinner and the shops there ( here on Google Maps) and head out to Agate Beach ( here on Google Maps) for a good view of the lighthouse.

Drive Time / Distance from Newport to the McKenzie River: 3 hours / 130 miles

Full disclosure here: this part of the itinerary requires a long drive, but we think it’s worth it because this part of Oregon might just be our favorite in the entire state.

The McKenzie River Scenic Byway follows the path of, you guessed it, the McKenzie River, which is one of Oregon’s many important rivers. For your purposes, we’d recommend driving it from the I-5 corridor (you’ll take Highway 126 from Eugene, which connects you to Highway 242) all the way to the eastern end in Sisters.

It’s a gorgeous drive, littered with waterfalls, tight switchbacks, alpine lakes, and lava flows.

There are a few things you need to know about this stretch. First, it’s closed outside of summer and early fall (usually open between July and October).

Second, it’s a narrow one way road, so it might not be best for RVs or trailers .

This is going to be a long day of driving, but ultimately we think it’s worth the journey. At some point, you have to cross over the state from the coast over to the Cascades, and it’s going to take 2-3 hours, depending on how you do it.

We went back and forth on whether or not to add a night here in Eugene, which would cut down on the drive time, but ultimately we think your time is better spent on a long drive today to give yourself some extra time in other places (which we think are more worthy of your limited time than Eugene).

Note: You’ll spend the night in Bend tonight, so we’re skipping the “where to stay” section here.

What to Do Along the McKenzie River Scenic Byway

Also, if you follow this itinerary as we’ve written it, you’ll be approaching from the west (coming from the Eugene area). We’ve organized the stops from west to east for that reason.

Proxy Falls: Over the course of this trip, you’re going to see a bunch of incredible waterfalls, especially as you get into the Columbia River Gorge later in the itinerary. Proxy Falls will likely be in your top three. It’s a short hike – roughly 1.5 miles – that takes you to a massive waterfall that cascades down the mossy rocks into Proxy Creek. You can do a loop that takes you to both Lower Proxy Falls and Upper Proxy Falls. The lower falls is the more impressive of the two, and the view from the base is incredible.

Scott Lake: This pristine lake is one of the spots we’re hoping to return to this summer. It’s a gorgeous lake with a perfect reflection of the Three Sisters (really two of the three sisters), one of the most distinctive natural features of central Oregon, and a bunch of first come, first served campsites along the lakeshore. However, the tradeoff here is the mosquitoes, which are intense in the early summer. For your purposes, we’d park along the lake and walk out to the western shore to get that reflection picture. It’s best in the afternoon, when the sun is behind you.

Dee Wright Observatory : As you ascend the tight switchbacks along the road as you pass Scott Lake, you’ll notice an abrupt change in the landscape. In what seems like a few minutes, you’ll go from dense evergreen forests to an open, rocky landscape. That shift is a result of a massive eruption of the Belknap Crater two millennia ago, and that dark rock stretching out as far as the eye can see is the resulting lava flow. The Dee Wright Observatory is an excellent stop not only to admire the lava flows, but because it gives you a great overview of the numerous rocky peaks surrounding you. This, my friends, is the heart of the Cascades in Oregon, and you’ll see the Sisters, Broken Top, Mount Washington, and Mount Jefferson, along with a handy key atop the Observatory to help you identify which is which.

Sisters: Sisters represents the end of the McKenzie River Scenic Byway, and the beginning of central Oregon and the high desert, which stretches for hundreds of miles to the east until you get into the Wallowas in eastern Oregon.

Sisters itself is a cute little town that’s a great base for adventures into the nearby Three Sisters Wilderness.

It’s a vaguely western-themed town, with some great spots to eat and drink ( Sisters Coffee and Sisters Meat and Smokehouse are good stops) and a cute little downtown area where you can do some window shopping.

Drive Time / Distance from the McKenzie River to Bend: 1 hour 30 minutes

Where to Stay in Bend: This choice basically comes down to whether you want to be downtown in the heart of all the action, or in a quieter locale. Stay at the Oxford Hotel in Downtown Bend for the best location in the middle of the action. Stay at LOGE Bend – we’ve stayed at other properties they own before – if you want to be right near the Cascade Lakes Scenic Byway.

Over the past decade or so (though it seems like it happened overnight), Bend has gone from being somewhat on the map, to being one of the most famous outdoor destinations in the western United States.

As you drive through the Cascade Mountains into the heart of Central Oregon, you’ll notice that the landscape starts to change.

First you hit the eastern foothills, which are notably more dry than the western foothills, and as you continue to Bend and beyond, you’ll be right in the heart of the high desert that stretches across Central Oregon.

Bend is perfectly placed between the mountains and the high desert. Within 45 minutes or so, you can be in the heart of the alpine paradise in the Cascades, or hiking through the desert dodging rattlesnakes in Smith Rock State Park (more on that in a second).

Within 45 minutes or so, you’ve got great hiking, cycling, skiing, watersports, and more. Plus, Bend itself has a pretty good food scene, the Deschutes River and all the watersports it has to offer, and perhaps the best selection of breweries in the country.

What to Do in Bend

Here are some things to do in Bend, including some of the things to do just outside of town along the Cascade Lakes Scenic Byway.

Hikes Around Bend: Within the Bend city limits, there are a few good hikes (we’re not counting the hikes in the mountains or at Smith Rock, which we have separate sections for below). Pilot Butte is right in the middle of town, and after a quick ascent you have a panoramic view of the surrounding landscape that serves as a nice introduction to Central Oregon’s geography. To the west, you’ll be able to see the snow capped peaks of the Cascades (there’s a topographic map to help you identify which peak is which). To the east, it’s a lot of flat land. We also have hiked pieces of the Deschutes River Trail , which heads south out of town along the river. You could follow the trail for miles and miles, but there’s a nice 2.7 mile loop that focuses on the part of the trail near the Old Mill District that would be a lovely way to spend a morning. It would look something like this . If you want something a little longer, continue south from Farewell Bend Park, which is where the trail gets a little less developed. For more information, read our guide to hiking in Bend .

Explore Downtown Bend: Downtown Bend is centered around Drake Park along the Deschutes River (there are several areas that could be confused as “downtown” so we wanted to clarify). There’s also the Old Mill District, which is a little bit south (and has more chain retailers and Red Robin vibes, if you know what we mean), and the Box Factory, which is between them. In downtown Bend, go to Lone Pine for coffee, The Lemon Tree for brunch (it’s popular so go early), and Bontà for gelato. Then, poke your head into the many shops and boutiques along NW Wall and NW Bond.

Brewery Hopping: Bend, like Portland, is known for its breweries. And like Portland, there are way, way too many breweries to visit in just a couple days. Here are a couple that we like for one reason or another.

Deschutes Brewing : In many ways, the OG Craft Brewery in Bend that set off the craft beer craze in Oregon. It’s still owned by the original owners (rather than Anheuser-Busch), which is cool. They do tours (which we’ve done and enjoyed), and they have an onsite taproom with beers that you can’t find elsewhere.
Silver Moon Brewing : A cozy taproom outside of town – we like them for their Thursday trivia nights! They have a cool space that has both indoor and outdoor seating with a lineup of live music in the summer. They also have a couple of food trucks onsite.
Crux Fermentation Project : Our friends who are beer nerds think this is the best beer in Bend (though they also note that there’s too many and they’re too different to really choose). What we like about them is their HUGE outdoor terrace, which is a perfect place for some cold beer after a morning of hiking.

Cider in Bend: If you’re more into cider (we are!), the small town of Tumalo just north of Bend has a couple of our favorite cideries in Oregon, and they’re just around the corner from each other. The first is Tumalo Cider , which has a nice taproom and great, dry ciders. The second is Bend Cider Company , which has a new-ish taproom a couple of blocks away. They do fun flavor combinations featuring fruits and botanicals (but not too sweet!) – we liked the Blackberry Ancho we tried recently. There’s a food cart pod across the street from Tumalo Cider which would make a good stop for lunch between cider tastings.

Tumalo Falls: Honestly, the hike to Tumalo Falls kind of sucks. But the waterfall is cool, so there’s that! It’s a 97 foot high plunge into Tumalo Creek, and if you do the six mile hike, you’ll reach the viewing platform and realize that it’s a five minute walk from the upper parking lot. We’d drive to the parking lot and check out the falls, saving your energy for a more interesting hike (there are many!) later.

Explore the Cascade Lakes Scenic Byway: This scenic drive (also known as Highway 372) leaves Bend, heading southwest out into the alpine paradise that is Deschutes National Forest. Skiers and snowboarders familiar with Oregon will know this stretch because it takes you out to Mount Bachelor, one of the state’s premier skiing destinations. Which, if we think about our other favorite hiking spots in the Pacific Northwest, is a great indicator of a good summer hiking destination. It’s worth spending a day driving the byway, starting in Bend and working your way down to Elk Lake before returning the way you came. You could also do a loop, taking NF-40 back towards Bend, but we’d prefer driving the more scenic byway both ways. This is a very popular stretch, and there is a permit you’ll need to enter during the peak summer season.

Hiking Along the Byway: The Cascade Lakes Scenic Byway is full of great hikes, particularly as you get out past Mount Bachelor. Here are a few good ones.

Green Lakes Trail : Potentially our favorite hike in central Oregon (technically it’s in the Cascades, so does that count as central Oregon?), this hike has everything we love about hiking in Oregon . Following a babbling creek the entire way, which is the perfect white noise for a hike? Check. Pristine alpine lake (really, lakes)? Check. All sorts of peaks to admire? Check. It’s 9 miles, but it’s an easy 9 miles, we think.
Tumalo Mountain Trail : A tough ascent, but the views from atop Tumalo Mountain are worth the sweat. You’ll have Mount Bachelor, the South Sister, and Broken Top right in your face, with various other peaks peeking out behind them. It’s basically straight up, straight down.
If you’re really up for a challenge, there are two excellent but difficult hikes here: Broken Top & No Name Lake and the South Sister . Both are very difficult, and should not be underestimated. The South Sister is going to be better if you can backcountry camp the night before at Moraine Lake or Green Lakes, which cuts down your ascent (but requires an extra night of backpacking, and all the associated gear).

Sparks Lake: We love Sparks Lake. The main photo on the homepage of this site (at the time of writing) was taken there on an early summer morning just after sunrise. Head to the day use area, park, and walk along the southeastern shore of the lake, where you’ll be treated to an absurdly good view of the South Sister and Broken Top, with a reflection in the still water of the lake if you’re lucky.

Day 9: Smith Rock State Park (and Drive to Government Camp)

Drive Time / Distance from Bend to Smith Rock State Park: 36 minutes / 23 miles

I will never forget the first time that I laid eyes on Smith Rock State Park during a spring trip to Bend with friends. I had only really ever been to Bend to go skiing in the winter at that point, which had us out in the forest to the city’s west at Mount Bachelor.

Smith Rock, with its winding river snaking its way between orange-hued rock formations, looks like it belongs somewhere in Utah or Arizona, not in Oregon. At least in my mind, having never explored Oregon east of the Cascades at that particular point in my life.

Bend is perched in the eastern foothills of the Cascades, and it is situated between the lush evergreen forests that cover the western part of the state, and the high desert that covers most of central and eastern Oregon.

Remember at the beginning of this guide, when we said that Oregon is the ninth biggest state in the country? Bend is about 25% of the way from the western border (the coast) to the eastern border with Idaho. Which means the high desert stretches for a LONG time from Bend to the east.

Smith Rock State Park is a destination that is definitely worth stopping at, but it’s not worth an entire section with separate things to do and places to stay. Instead, we’d recommend a stop on the way from Bend up to Mount Hood. It’s a perfect location for that.

There’s really only one hike in Smith Rock State Park – though you can do it two ways – and that’s the Misery Ridge Trail . It’s accurately named, because the initial ascent up to Misery Ridge is brutal, especially on a hot summer day with full exposure to the sun.

The views from the top of the ascent, though, are worth the price of admission. You’ll have a panoramic view of central Oregon, with the snowy peaks of the Cascades to the west, and the high desert stretching out as far as the eye can see to the east.

On the descent, you’ll pass Monkey Face, a very popular destination with rock climbers. It is also accurately named, because from a certain angle, it looks exactly like the face of a monkey.

The trail descends back down to the river, where you can either head left to return on the River Trail (shorter and flatter) or right to continue on the Summit Trail (longer with better views and more climbing) to finish the loop.

Note: This is another place where you’ll stop along the way to another destination – in this case Mount Hood – so you’ll spend the night in and around Government Camp after your exploration of Smith Rock.

Days 10-11: Mount Hood (Government Camp)

Drive Time / Distance from Smith Rock to Mount Hood: 1 hour 40 minutes / 86 miles

Where to Stay at Mount Hood: There aren’t that many places to stay here, but you do want to be in or around Government Camp on the south slopes of the mountain. There’s a Best Western , a campground at Trillium Lake that we like, and a bunch of nice cabins in the woods to choose from.

Mount Hood is our favorite hiking destination within a couple of hours of Portland. We fell in love with it on that first road trip that eventually led us to move here, and we go back there as often as we can.

Matt is from Seattle, where the towering peak of Mount Rainier is a near constant reminder of the natural beauty that lives just outside of the sprawling city (and also a constant barometer of the weather – “is the mountain out?” is a common question to evaluate whether it’s a nice day in Seattle).

Mount Hood plays a similar role for Portland, and we often have a similar conversation around Portland around whether Hood is out.

During the winter, Mount Hood is home to some of Oregon’s best skiing. Then, when the snow melts in the late summer, it turns into a veritable alpine wonderland, with wildflowers blooming, roaring waterfalls, and stunning vistas of Mount Hood around every bend in the trail.

The part you’re going to want to focus on here is the area in and around Government Camp , on Mount Hood’s southern side.

That’s where all the action is, though that’s not to say there aren’t worthwhile places to visit on other sides of the mountain.

By focusing there, you’re also nicely positioned for the next stop on your itinerary, Hood River, where you’ll just hop back on Highway 26 and continue north to Oregon’s northern border.

What to Do at Mount Hood

Here are some of our favorite things to do and see near Mount Hood.

McNeil Point (or Bald Mountain via Lolo Pass): For some of the best views in Oregon, you should hike one of these two trails. However, be warned, the hike up to McNeil Point is no joke. Not even a little bit. We did it at the peak of our hiking powers, during a summer where we were hiking 7-8 miles almost every day, and it kicked our butts. With that warning out of the way, it’s a fantastic hike. It takes you up to an alpine wonderland on Hood’s northwestern slope where you’ll have unobstructed views of the mountain, and you’ll feel like you’re close enough to reach out and touch it. The full hike to McNeil Point is a 10 mile lollipop – you should do the lollipop section counterclockwise because it involves a scramble that is easier to do uphill (you can also go around and make it an out and back, but it’s about 2 miles longer).

Our favorite view in Oregon is the view from Bald Mountain: You’ll find it plastered all over this website – which you can access either on the way up to McNeil Point, or as a different, much easier hike from the Lolo Pass Trailhead. That’s a good shorter option that is more accessible for more hikers.

Ramona Falls : If you want a waterfall hike, this is it. Don’t let the 7 miles scare you off – it’s a pretty easy hike with the exception of the crossing of the Sandy River, which used to have a bridge, but has since been relegated to “I don’t know, find your own way across.” It’s not an easy one, though it is worth noting that hundreds of hikers do it every day in the peak of the summer. There are various logs, and some narrower sections of the river a bit upstream from the trail where you can make the crossing. We wouldn’t take our dog, though. Ramona Falls, unlike some of the waterfalls in the Columbia River Gorge, is a wide cascading falls that dribbles down a rock wall rather than plunging down into a pool. Still, it’s very impressive, and it’s 120 feet tall – tall enough that it’s hard to get the whole thing in frame on a photo without a wide angle lens.

Timberline Lodge and the hike to ZigZag Canyon: The iconic Timberline Lodge is an uber-rustic lodge that is reminiscent of the various national park lodges in the American West. It was built in 1937, and has since been declared a National Historic Landmark. If you’re up for a splurge, their rustic rooms would be a fun place to stay. However, even if you’re not staying here, it’s worth coming up to do some exploring on the trails around the lodge (in the summer, anyway, it’s a ski resort during the winter months). Our favorite of the bunch is a piece of the Timberline Trail, which circumnavigates Mount Hood, and it’s the stretch between the lodge and Zigzag Canyon . It’s a beautiful, somewhat easy hike that ends with a view of the peak up a canyon.

Trillium Lake: This is our favorite campground in Oregon, although it’s also one of the most competitive. We’ve camped here a few times, and we’ll do it again. The draw here is the excellent views of Mount Hood, often reflected in the surface of the lake, which you can find from the southern end of the lake near the day use parking. It’s also a great place to bring watercraft like kayaks and stand up paddleboards in the summer.

Drive Time / Distance from Government Camp to Hood River: 50 minutes / 43 miles

Where to Stay in Hood River: Hood River is a very nice little downtown area, and there aren’t that many places to stay downtown. We actually like staying across the river in Washington, either at the Society Hotel in Bingen or at the lovely RubyJune Inn (a very charming B&B in a tranquil setting run by lovely people).

The Columbia River Gorge runs along the northern border of Oregon (it separates Oregon from Washington State), and has the highest concentration of waterfalls in the state.

Depending on how good your memory is (and how long ago high school was for you), you may remember the Columbia River from your days learning about Lewis and Clark, because it’s the river that they came up as they made their way out to their final destination just south of Astoria.

Living in Portland, the Columbia River Gorge is essentially our backyard. It takes 30-40 minutes for us to get out there, and when we’re looking for an easily accessible hike for a random Thursday morning, this is generally where we’re heading.

It’s also on our itinerary for every single first-time visitor who comes to Portland to visit us.

There is a nice mix of different hikes in the Columbia River Gorge , from easy waterfall hikes to hikes that climb to the rim of the Gorge, where you’ll find dramatic vistas out over the Columbia River and the gorge beyond.

Hood River is a town in the Columbia River Gorge, and it is perched at a crossroads of sorts. It sits at the point where the wet, temperate climate of western Oregon transitions to the dry, more extreme climate of the high desert in eastern Oregon.

To the west, you’ll find some of the best waterfalls in Oregon. To the east, the high desert. And both north and south are the Cascade Range, and places like Mount Hood and Mount Adams.

There are a bunch of great things to do in Hood River, and that list grows longer when you include the fertile Hood River Valley and its fruit trees as far as the eye can see and the wineries along the Columbia River.

Hood River is a great home base to use to explore the Gorge and the fertile Hood River Valley, which is what you’ll be doing for this stretch of the itinerary.

Note that we’ve split the “what to do” sections below into Hood River and the Columbia River Gorge to make it easier for you to plan and group things together.

What to Do in Hood River

Here are a few of our favorite things to do in and around Hood River.

Tamanawas Falls: This hike is on the eastern slopes of Mount Hood, and would be an excellent stop between Government Camp and Hood River. It’s right on Highway 26, and it’s a nice, easy hike up to a spectacular waterfall. Parking is limited, so you’ll want to get there early, or be prepared to wait for a spot in the tiny lot – parking along the highway is illegal, and we’ve seen many people get tickets here.

Read More: Everything You Need to Know to Hike the Spectacular Tamanawas Falls Trail

Drive the Fruit Loop: The Hood River Fruit Loop is a perfect half-day activity near Hood River that takes you through the fertile Hood River Valley, with apple and pear trees as far as the eye can see (with backdrops of Mount Adams, Mount St. Helens, and Mount Hood). There are a bunch of worthwhile stops here, but our favorite is Draper Girls Country Farm , which does u-pick cherries for a short window in the summer, and has all around excellent produce more or less from spring to fall. They have a lovely back patio area with great views of Hood, and a lush collection of various fruit trees. Plus, a great selection of locally made jams, honeys, and other stuff inside the shop.

Wine Tasting near Hood River: The area around Hood River, both on the Oregon side of the Gorge, and on the Washington side, is a great place to grow grapes and make wine. There are a bunch of wineries in Hood River itself ( Hood River Common House is a good spot), but the real way to do it is to hop in the car and drive out to one of the wineries dotting the landscape around Hood River. We like the Gorge White House (not the best wine and cider, but the setting is amazing) and Loop de Loop (the friendliest wine makers and the best dog, plus an amazing view), and have also heard good things about AniChe Cellars , Le Doubblé Troubblé , and Analemma Wines (this one came highly recommended from the folks at the Ruby June Inn, where we stayed on our recent trip).

What to Do in the Columbia River Gorge

Here are our favorite stops in the Columbia River Gorge.

Wahclella Falls: This is the best bang-for-your-buck waterfall adventure in the Columbia River Gorge, we think. Multnomah Falls is great, yes, but it’s an absolute zoo at all hours. The short and easy hike out through a canyon with steep rocky walls here weeds out most of the visitors, and you end up at a beautiful waterfall that tumbles off of a ledge into a pool 65 feet below.

Read More: Everything You Need to Know to Hike the Wahclella Falls Trail

Drive The Historic Columbia River Highway: The Historic Columbia River Highway runs from the town of Dodson, just west of Bonneville (and the dam of the same name), all the way to the town of Troutdale, which is just east of Portland. It’s a windy two lane road that parallels I-84, and is the original road that was used to traverse the Gorge on the Oregon side. Our recommendation would be to drive it from Multnomah Falls to its western terminus, because there are routinely huge traffic jams along the road at the base of Multnomah, and it’s better to park in the big lot along I-84.

Multnomah Falls: Multnomah Falls is the queen of the waterfalls in Oregon. It’s by far the most impressive waterfall in the state, we think, and it’s actually the biggest tourist attraction in Oregon thanks to its location about 40 minutes away from downtown Portland. It’s a two-tiered waterfall that, all-in, falls 620 feet down from the top of the rocky ledge high above the viewing platform. The only issue we have with Multnomah Falls is the fact that, at any given moment, you’re likely to be sharing the experience with around 1,000 of your closest friends. It’s worth seeing, but there are so many other waterfalls in the Gorge to get to with a fraction of the visitors (especially if you’re willing to hike a little bit). Oh, definitely park at the bigger parking lot along the freeway ( here on Google Maps) – the smaller lots at the base of the falls are an absolute nightmare, and we’ve seen massive backups along the Historic Columbia River Highway of people just waiting to get a spot. The bigger lot has more parking, and you just have to walk a few hundred feet to get to the falls.

Latourell Falls : Lower Latourell Falls is one of the most scenic waterfalls in the Gorge after Multnomah, particularly in the winter when the water level is high AND there’s a bright greenish-yellow moss covering the rocks on either side of the falls. The lower falls is the more impressive, we think, as it falls 225 feet off of a ledge in one single drop. There’s a nice wooden bridge at the base of the falls, which is a short hike from the trailhead that is a must-do, that is a good spot for pictures. There’s a nice, relatively easy two mile loop hike that takes you up to the Upper Falls and down around to the base of the lower falls that is a worthy excursion if you have the time and energy.

The Vista House & Portland Women’s Forum Scenic Viewpoint: These are two excellent viewpoints at the western end of the Historic Columbia River Highway to cap off a day full of great views. Pictures are worth 1,000 words here, we think, so here’s a few we’ve gotten from up here.

Day 14: Explore Portland

Drive Time / Distance from Hood River to Portland: 1 hour / 63 miles

Where to Stay in Portland: Portland is – by far – the biggest city in this guide, so we’d recommend reading our in-depth guide to choosing a place to stay in Portland for the information you need to make the best choice for you (which takes more than a couple of sentences).

What can we say about Portland? We have fallen head-over-heels in love with our new home. Everyone always talks about the “weirdness,” which we have come to understand as an implicit permission to be whoever you want to be.

That idea flows through to the unique small business culture that exists in Portland, where you can find all sorts of locally made foods, crafts, and home goods.

The funny part about Portland is that there aren’t really any big name tourist attractions. Seattle has the Space Needle, San Francisco has the Golden Gate Bridge, and Portland has… a donut shop and an independent bookstore? But, honestly, that’s kind of why we love it. It’s not that there isn’t a lot to do – there’s plenty of amazing things to do in Portland.

The food scene? The best on the west coast (except for maybe L.A.). There’s a culture of innovation – which we think is at least partially driven by the food cart scene that allows for low-cost experimentation (versus opening a brick and mortar location).

The access to the outdoors? Between the excellent parks in Portland and the access to the mountains, Gorge, and coast, it’s hard to beat.

We’re in love with our home, and think you’ll like it too.

Unfortunately for you, your time here is limited, and we’ve intentionally chosen to weight this road trip towards Oregon’s natural beauty, which means you’re left with about a day, maybe a day and a half to explore the biggest city in the state.

If you have an extra day or two, it’s absolutely worth adding time here.

What to Do in Portland

Now, there are way too many things to list here, so we’re going to focus on our top five here.

Powell’s City of Books : The fact that we’re starting with an independent bookstore – the largest in the world, no less – tells you just about everything you need to know about Portland. It’s right in the heart of downtown Portland, and is an astounding collection of books from all genres. This place is amazing, and even since we’ve lived here I can’t walk out of here with at least one book. I bought a light blue Powell’s Books t-shirt on clearance almost a decade ago that I wear often, and every time I wear it outside of Portland (usually in Seattle) at least one person stops me to chat about how much they love Powell’s. They have an extensive collection of books, including big sections dedicated to fantasy/sci-fi, Pacific Northwest history, and graphic novels. We especially like the staff picks section in the entryway, which is a nice way to see what the staff are reading and recommending at the moment.

The International Rose Test Garden : Washington Park – which is the park where this rose garden is located – is the best park in Portland, and is home to a bunch of different attractions including the Oregon Zoo and the Portland Japanese Garden. But the Rose Garden, which is both free and spectacular, is the best of the bunch, we think. There are 10,000 roses here, and when they’re in full bloom between roughly May and September (sometimes longer), it’s quite a sight to behold.

Breakfast / Brunch in Portland: Portland is an excellent food city in general, especially when you consider prices are going to be about 25% lower than other cities on the west coast. However, it really shines in the morning, when you’ll find some world-class breakfast and brunch options.

Now, you might expect to see Voodoo Donuts on this list.

The novelty donuts are fun, yes, but it’s far from undiscovered, and there are honestly much better doughnuts to be had in Portland. Like, a lot of them. Go to Blue Star , Doe Donuts , Coco Donuts , or Petunia’s Pies and Pastries (for gluten free and vegan donuts) if you’re in and around Downtown Portland.

Here are some of our favorites, in no particular order.

Fried Egg I’m in Love : Award-winning breakfast sandwiches! They have a food cart in downtown Portland, along with a brick & mortar shop on Hawthorne Blvd in Southeast Portland and up on Mississippi Avenue.
Ken’s Bakery : The best bakery in Portland, probably. It’s in northwest Portland, and is a local favorite with a rotating selection of pastries that you can see them making right behind the register. Good sandwiches for lunch, too, but the hero is the pastries in the morning.
Pip’s Original Doughnuts & Chai : Go for the mini donuts (they are NOT donut holes, Matt!) with innovative flavors, stay for the incredible chai. There’s a perpetual line, especially on weekends, so go when they open if you can. Alysha LOVES their chai (get a chai flight!).

Explore The Eastside: While most of the tourist attractions like Powell’s and the Rose Garden (though Powell’s has a location on Hawthorne) are on the west side of the river, we actually like the east side of the river more. We’d divide this large and sprawling area into three distinct areas. If you’re staying downtown and don’t have a car, your best bets are going to be:

The Central Eastside: Just over the river from downtown, this area is an old industrial district that has become a great place to spend an afternoon, with all sorts of places to eat and drink. We like Schilling Cider House (for 50 taps of different ciders), Cascade Barrel House (for beer), and the Revolution Hall Rooftop for drinks with panoramic views of Portland and Mount Hood).
Southeast Portland: Our neighborhood! Centered on Hawthorne Blvd and Division St, this stretch runs straight through a residential neighborhood and is full of places to eat and drink. Fried Egg I’m in Love (breakfast sandwiches), Cibo (pizza), Lauretta Jean’s (pies), Pinolo Gelato (gelato), Magna Kusina (Filipino), and Oma’s Hideaway (Malaysian / Singaporean food) are the spots we’d hit.
Mississippi Avenue: Where we used to live! The stretch along Mississippi Avenue might be the most bang-for-your-buck in terms of the amount of bars and restaurants packed into a relatively short stretch. For food, Lovely’s Fifty-Fifty (of Chef’s Table fame), Kate’s Ice Cream (plant-based ice cream), and the food cart pod at Prost . For drinks, go to Interurban . For shopping, don’t miss the Meadow , a store that we go to far too often with salt, chocolate, and bitters.
The Alberta Arts District: The furthest from downtown Portland, Alberta Street is one of the main corridors in northeast Portland. Similar to the other places on this list, it’s packed with great food, drinks, and coffee. For coffee, don’t miss Proud Mary (our top coffee shop in Portland for fun single-origin coffees) and Barista . For food, go to Tin Shed Cafe for brunch, Zilla Sake for excellent sushi and sake, and Matt’s BBQ Tacos for…tacos. For drinks, Bye and Bye for good drinks and vegan food, and Great Notion Brewing for beer (and the aforementioned Matt’s BBQ Tacos, which operates on their patio).

For more, we’d encourage you to head over and read our other Portland guides.

What to Add with More Time in Oregon

Like we’ve said time and time again, two weeks is not really enough time to see everything there is to see in Oregon. Here are a few more things to consider adding if you happen to have more time.

More Time in Portland (+1-2 Days)

As we mentioned above, we intentionally decided to weight this itinerary towards Oregon’s natural beauty and have you spend the vast, vast majority of your time outside of cities.

Which, unfortunately, leaves you with just over a day to explore Portland.

Ideally, you’d spend two or three days in Portland, which is one of the most underrated food cities (quickly transitioning to “appropriately rated”) cities in the country.

There’s a strong culture of experimentation and innovation in Portland’s food and drink scene that puts it on the leading edge of food trends that make it a great place for people who love to eat to explore.

With an extra day or two, you can experience the things that we love about Portland at a more comfortable pace – the amazing green spaces inside the city, and the thriving food and drink scene to name a couple.

If you have the extra time, we have guides to 2 days in Portland and 3 days in Portland (which includes a half day trip to the Gorge, which you could replace with the trip to Silver Falls just below this) which will give you a play-by-play of exactly how we’d spend your time.

Day Trip to Silver Falls State Park (+1 Day)

Silver Falls State Park is a hair over an hour south of Portland, and it’s home to one of our favorite hikes in the state – the incredible Trail of Ten Falls . Which, as you might imagine, features 10 waterfalls over the course of a relatively easy eight mile trail.

If you want waterfalls – and especially if you’re here in the spring and early summer when the water is high – this is as close to a must-do as it gets.

After your hike, you can meander through the eastern end of the Willamette Valley on your way back to Portland, stopping at Bauman’s and E.Z. Orchards for farms and cider (and apple cider donuts!).

The tiny town of Silverton is a nice place to stop for lunch after the hike (or just wait until you get back to Portland and check off some other places there!).

If you do want to stay overnight, the campground at Silver Falls is really nice. However, other than that, there’s really not a whole lot of places to stay nearby, and you’re probably better off making it a day trip and staying in Portland for another night.

Crater Lake National Park (+1-3 Days)

So you want to add Crater Lake National Park to your Oregon trip?

Well, we have good news and bad news.

The good news is that it’s totally doable as long as you have a little extra time.

The bad news is that it’s only really accessible for a few short months a year, and it’s not really convenient even when it’s at its most accessible. It’s at the southern edge of the state, and it’s fairly far from just about everything else on this itinerary.

To add Crater Lake to the itinerary, you’re going to want to do it after Bend. It’s about 90 minutes from Bend to the north rim of Crater Lake, which doesn’t seem so bad, right?

However, there is one major caveat here, and that’s the fact that the rim road that circles around to the north end of the rim is closed during the winter and early spring due to snow.

It will start to open in early spring, but when exactly that happens totally depends on the year.

That’s an issue to keep in mind because Bend is north of Crater Lake. The only way to access the small slice of the park that’s open between November and April (roughly), which is on the south rim, is to enter the park through the south entrance. Which is about three hours from Bend.

We would only really recommend adding Crater Lake during the summer and early fall (call it June through October) when roads will be mostly open, and hiking trails will be mostly snow-free.

Add it as an overnight trip from Bend, and continue along on the McKenzie River Scenic Byway as written.

What to Do with Less Time in Oregon

With less time – 7 or 10 days in Oregon – we’d make some adjustments and be more focused with your time. With 5 days in Oregon, we’d go ahead and spend the entire time in Portland, doing day trips out to the Gorge, the Coast, and Silver Falls to fill your time (you’d want to rent a car for that trip).

With 7 days , we think you have time for a nice little loop that encompasses Portland and the mountains OR the coast, but probably not both.

If you absolutely have to see both, you could add a day on to do a day trip out to the coast (Cannon Beach or Astoria) or the Columbia River Gorge (Hood River).

With 10 days , you have enough time to comfortably do a figure-8 that includes the mountains (Hood River and Mount Hood) and the coast (Cannon Beach and Astoria).

Here’s a day-by-day breakdown of what those itineraries might look like.

7 Days in Oregon: The Mountains

Here’s what a perfect 7 days in Oregon might look like, focused on the northwest corner of the state around Portland.

Add a day if you want to do a day trip out to the coast (and read our guide to the best day trips from Portland ).

Day 1: Arrive in Portland, drive to Hood River
Day 2: The Columbia River Gorge
Day 3: Hood River & Around
Day 4: Mount Hood
Day 5: Mount Hood
Day 6: Portland
Day 7: Portland & Fly Home

7 Days in Oregon: The Coast

Add a day if you want to do a day trip out to the mountains, and focus on Hood River or Mount Hood.

Day 1: Arrive in Portland, drive to Astoria
Day 2: Astoria
Day 3: Cannon Beach & Around
Day 4: Tillamook & Three Capes Scenic Loop
Day 5: Drive to Portland

10 Days in Oregon

With 10 days, do a loop starting and ending in Portland that takes you first out to the mountains (and the Gorge), then head west out to the coast for a couple of nights before returning to Portland.

Day 6: Drive to Cannon Beach
Day 7: Cannon Beach & Around
Day 8: Tillamook & Three Capes Scenic Loop
Day 9: Drive to Portland
Day 10: Portland & Fly Home

Dry Creek Falls via the PCT: A Complete Trail Guide

What to Do in Astoria, OR: Complete Guide for First Timers

A Complete Guide to the Best Mount Hood Hikes (+ Map)

Hiking the McNeil Point Trail: A Complete Trail Guide

The Multnomah – Wahkeena Falls Loop Trail: A Complete Guide

Hiking the Amazing Tamanawas Falls Trail: A Complete Guide

Omg.. I cannot tell you how well written and amazing guide this is. Everything is broken down so well and easy to understand. Loved your blog and have already fallen in love with all the pictures of the falls and mountains you have on this blog. Thank you for writing this up.. Will surely use this guide when we plan to travel.

Thanks for the kind words, Kina!

Hi! We are Jake and Kaylee.

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The Globe Wanderers

Oregon , USA · May 4, 2020

Our 7 Day Oregon Road Trip Itinerary

Part of our heart with forever belong to the state of Oregon. Oregon is by far one of the perfect places to road trip. It is home to some of the most amazing mountains, hot springs, lakes, coastline, and waterfalls in the United States.

To help you explore this incredible state, we have put together a comprehensive 7 day Oregon road trip itinerary that includes must see places and camping tips!

Things to Know before you go!

Best Time to Visit Oregon: Summer and Early Fall is the best time to visit Oregon and is considered peak season. Spring, late Fall and Winter may hinder your ability to visit some areas due to snow!

Let’s get started!

Need accommodation ideas for your PNW Road Trip? Check out our blog post on the most amazing Airbnbs in the Pacific North West!

Day 1: Arrive in Portland/ Cannon Beach/ South Beach State Park
Day 2: Bandon Beach/ Samuel H Boardman Scenic Corridor/ Brookings
Day 3: Crater Lake/ Toketee Falls
Day 4: Umpqua Hot Springs/ Bend
Day 5: Abiqua Falls/ Silver Falls State Park
Day 6: Trillium Lake/ Mount Hood/ Lavender Field
Day 7: Lost Lake/ Rowena Crest Viewpoint/ Multnomah Falls/ Portland

Oregon Road Trip Day 1

First stop: cannon beach..

Cannon Beach is 90 minutes North West of Portland on the Coast of Oregon. This beach is famous for the Haystack Rock formation. The little town is filled with tons of quaint shops and family owned restaurants to explore! This is the perfect way to start your epic road trip!

This is a popular beach for Hollywood films. You might recognize it from Twilight and The Goonies.

Second Stop: Devil’s Punch Bowl.

During low tide in the summer you can follow the coastal trail and actually walk inside of it. However during the fall and winter months the water level rises and this isn’t possible. It was still incredible to see from an aerial view!

Day 1 Accommodation Options:

South Beach State Park: This incredible state park offers a range of camping options with clean washroom and shower facilities.
Rent a local Airbnb: We love staying in Airbnb’s when we travel! If you have never rented an Airbnb before, use our code to get $$ of your stay!

Oregon Road Trip Day Two

First stop: bandon beach ..

This is an incredible spot with some of the most unique rock formations that we have ever seen! We

Second Stop: Samuel H Boardman Scenic Corrido r

This is a 12 mile stretch along the coastline and was one of our favorite parts of our entire trip. You could honestly spend a few days here and still have so much to explore.

Below we put together a list of the most popular stops in this corridor and the approximate mile markers associated with them!

Make sure to write these down before you head here. Some of the stops we listed aren’t mentioned on roadside signs!

Mile Markers for the Samuel H Boardman Corridor

Arch Rock (Mile 344.8)
Spruce Island (Mile 345.0)
Thunder Rock Cove (Mile 345.8)
Natural Bridges (Mile 346.0)
North Island (Mile 347.4)
Thomas Creek Bridge (Mile 347.8)
Indian Sands (Mile 348.6)
Whaleshead Viewpoint (Mile 349.3)
House Rock Viewpoint (Mile 351.2)
Cape Ferrelo Viewpoint (Mile 352)
Lone Ranch Picnic Area (Mile 352.6)

Third Stop: Brookings

Brooking’s is a small town with a lot of mom and pop style shops and local restaurants. It was also a great place to stock up on some essential items at the Fred Myer (grocery store)!

We ate dinner at Oxenfre Public House in Brookings. Its currently rated the #2 restaurant in this little town and was the Trip Advisor’s Traveler’s Choice in 2020.

Day 2 Accommodation Options :

Harris State Beach Park: This campground was one of our favorites during our entire trip in Oregon. We watched once of the most incredible sunsets on the beach that this campground sits on. They have a wide variety of camping options and clean washrooms with showers. For more information on booking here, check out this link!

Oregon Road Trip Day 3

This day was the most action packed day of our entire trip!

Start by taking Highway 199 Scenic Byway which leads you through one of the most scenic drives in the USA.

This highway passes through the Jedediah Smith Redwoods State Park . This is an incredible opportunity to see some of the most beautiful trees in the world.

First Stop: Crater Lake

Crater Lake National Park is a bucket list place for many. The water of the lake is an incredible color of blue. There are so many things to do here, we have listed some of our favorites below!

Things to do at Crater Lake:

This hike is one of the most popular hikes in the park. It leads to a fire lookout. This trail takes about 1 hour round-trip and is the best place to catch the Sunset.
This trail is 2 miles in length and traces the rim of Crater Lake. This trail is relatively easy to do and offers some incredible perspectives on the lake.
A hike down to Cleetwood Cove with lead you to the only spot at the lake that you can swim! The water temperature ranges from ranges from 0°C to 19°C so on a hot day it will be refreshing!

Stop Two: Toketee Falls .

There is a small parking lot at the trailhead. The 0.8 mile hike to the main lookout point was very easy and incredibly rewarding. To get to the viewpoint in our photo below, you have to climb down from the main path to the

Day 3 Accommodation Options:

Toketee Lake Campground : This is a rustic campground with very basic amenities. This campground does not have running drinking water, so make sure to bring plenty with you! They also only have outhouses and they do not have showers.
Luxury Glamping Tent: This Airbnb is a glamping resort located just a short drive away from Toketee Falls and Crater Lake. There are fire rings, washrooms and showers available here! Check out their link here!

Oregon Road Trip Day 4

F irst stop: umpqua hot springs.

Located only a few minute drive from Toketee Campground, this is the perfect way to start the morning.

Tips for visiting Umpqua Hot Springs:

Arrive early in the morning to avoid any crowds. We got there at 7:30 and we had to all to ourselves for over an hour!
It is a 0.8 mile hike to the Hot Springs from the parking lot. Make sure to wear running shoes as it is a moderately difficult trail.
There are bathrooms at the trailhead but there are none once you reach The Hot Springs themselves.
Nudity is acceptable at Umpqua so be prepared and be respectful when taking photos.

Second Stop: Bend

The city of Bend is an outdoor lover’s paradise and a craft brewery mecca. There are over 22 breweries in Bend! Bend has a beautiful downtown filled with local shops and restaurants right along the river.

Some of our favorite places in Bend were:

Get here early as it fills up fast. This is possibly the best breakfast you will ever have.
Located along the river, they have indoor and outdoor seating as well as lawn games!
Cascade Lakes Brewery
Dudley’s Bookstore and Cafe
The Bend River Wave
People from around the world travel here for skiing in the winter and mountain biking in the summer!

Accommodation Options Bend:

Stay at the Loge: This hotel was completely renovated and is one of the most popular spots in Bend. All rooms come equipped with hiking and camping gear that is free to use during your stay! They also have free city bikes that we used to explore Bend, as well as fire tables and a cafe!
Dome Airbnb: This Airbnb is seriously so unique and is in a great location! Check out their link here!

Oregon Road Trip Day 5

First stop: abiqua falls.

We left Bend very early in the morning as it is approximately a 3 hour drive to the Abiqua Falls Trailhead. This trail is a 5.3 mile out and back from the trailhead itself.

Reaching the trailhead can be tricky as the road can be washed out at times, leaving large potholes that are difficult to navigate around. We drove as far as we could down the road (considering we were in a rented campervan) and then decided to walk the rest of the way.

This trail is rated as difficult as it is very muddy and requires the use of ropes to navigate in some sections. This hike was incredible and Abiqua Falls is unlike anything we have ever seen before. You HAVE to hike this.

Second Stop: Silver Falls State Park

We hiked the Trail of 10 Falls, which is a 7.6 mile loop trail that features 10 incredible waterfalls and is the most famous trail in the park.

Day 5 Accommodation:

Silver Falls State Park: The campground here is beautiful and the facilities are well kept. This was the perfect place to spend the night! It is also close to all of the hiking trails which makes exploring this State Park very easy.

Oregon Road Trip Day 6

First stop: mount hood area.

Things to Do in the Mount Hood area:

A beautiful lake with the stunning backdrop of Mount Hood
If you are visiting Mount Hood in the winter time, this is an incredible and bustling Alpine Village.
This is the famous hotel featured in the movie The Shinning
This Lavender Farm offers some of the most picturesque views of Mount Hood
Make sure to check their Facebook Page for their hours and operating months.

We then attempted to visit the Lavender Valley close by but unfortunately it was closed… so we took this photo across the street from the Lavender Field!

Day 6 Accommodations

Lost Lake Campground: This campground is set on the shores of Lost Lake, and offers some incredible adventures and beautiful views of Mount Hood. They have Yurts, Lodge Rooms and campsites available making this an experience for everyone! Check out their website here.

Oregon Road Trip Day 7

Stop one: lost lake campground.

We decided to rent a paddle boat right after sunrise and we took in some incredible views of Mount Hood from the lake.

After our morning on the lake, we decided to head back towards Portland where we stayed the night before flying back home!

Second Stop: Rowena Crest Viewpoint

This is one of the most photographed roads in the state of Oregon and offers incredible views of Columbia River and the State of Washington.

Third Stop: Multonomah Falls

This is one of the most photographed places in the State of Oregon. We recommend getting here early in the morning prior to the tour buses as this place can get busy quick.

Fourth Stop: Mississipi Ave, Portland

This street was SO MUCH FUN! Tons of local restaurants, outdoor and indoor bars and little locally owned shops. We spent the entire afternoon and evening exploring this street and all it had to offer. We highly recommend this spot if you are looking to stay out of downtown Portland.

Things To Add To Your Oregon Road Trip

As we said earlier, we only had 7 days to pack in as much activity as we possibly could. That being said, there are so many things left that we didn’t get to see. When we return we want to visit the Painted Hills, Smith Rock State Park, more amazing hot springs, more waterfalls and explore more of the Columbia River Gorge.

Final Thoughts

We love Oregon. We will be returning to continue exploring all of its incredible magic someday. If Oregon is not on your bucketlist, it needs to placed on there immediately. This state is unlike any place you will ever visit in your life. It has such a unique set of landscapes. From gorgeous coast lines, hundreds of powerful waterfalls, vast desert and tall mountains, this place really has it all!

We hope that you found this blog post helpful! Let us know in the comments below if you have been to Oregon and what your favorite places were!

Happy Travels 🙂

Jake and Kaylee

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How to plan an unforgettable 7 day Oregon road trip

Oregon has been on my bucket list ever since I moved to Vancouver, BC, back in 2019. Fast forward four years and I finally made it down there! On our 7 day Oregon road trip, we experienced so much – from incredible beaches and sand dunes to roaring waterfalls and the high desert.

Oregon is such a large and diverse state which can make planning a road trip quite challenging. In this blog post, I’m sharing our exact 7 day Oregon itinerary. You’ll also find optional add-ons in case you want to extend your trip, information on entrance fees, suggestions on where to stay, and more!

Disclaimer : This blog post features some affiliate links, which means I get a small commission if you make a purchase. There’s no extra cost to you but it just helps me to keep writing these free guides and itineraries for my readers. Thank you for your support!

7 day oregon road trip: what you need to know.

There are so many wonderful things to see and do in Oregon. This 7-day Oregon itinerary is based on my own experiences but you can easily tailor this to your own travel style and add or cut any stops you see fit.

7 Day Oregon Road Trip Route Overview

Here’s a quick summary of the 7 day Oregon road trip that we did. You can do this route in either direction. We went anti-clockwise as the weather looked better at the beginning of the trip so we decided to start with the coastal section.

Day 1: Arrive in Cannon Beach
Day 2: Cannon Beach, Ecola State Park, and Cape Kiwanda
Day 3: John Dellenback Sand Dunes, Willamette National Forest, and Bend
Day 4: Bend
Day 5: Smith Rock State Park and Mt. Hood
Day 6: Columbia River Gorge (and Portland)
Day 7: Travel home

Below you’ll find an itinerary map for this Oregon 7 day road trip which features pins for each day’s scenic stops, hiking trails and places to eat. You can save the map by clicking on the star next to the title and use it to help gauge daily driving distances.

Before we jump in, here are some important things to know about Oregon and this road trip route:

Oregon is a big state

Oregon is a lot bigger than people realize. It’s actually the 9th largest state in the country which means you’re not going to see the entire state in one trip. Here’s a quick overview of the different regions:

Oregon Coast: 363 miles of beaches, rugged cliffs, sea stacks and quaint towns
Central Oregon: Home to the high desert and well-known spots like Bend, Sisters and Smith Rock State Park
Eastern Oregon: This is a vast area that deserves its own road trip and includes the Painted Hills, Pendleton and Hells Canyon
Mt. Hood: Mt. Hood is the highest peak in Oregon and is a popular destination for outdoor enthusiasts
Columbia River Gorge: This is the ‘waterfall wonderland of the Pacific Northwest’
Willamette Valley: The valley is home to vineyards, farmlands and orchards
Southern Oregon: This is a diverse region where you’ll find Crater Lake National Park, Oregon Caves National Monument and hidden hot springs

We wanted to try and see as much of the different landscapes as we could on our 7 day Oregon road trip. We spent some time on the coast before driving into central Oregon and up to Mt. Hood and the Columbia River Gorge.

This itinerary doesn’t include Eastern or Southern Oregon as it was just too far to go on a 7 day Oregon road trip. If you do have more time, I’ve included some suggestions on how to extend this road trip later in the blog post.

Where to start and end your 7 day Oregon road trip

This really depends on where you’re travelling from. We decided to drive from Vancouver so we went straight to Cannon Beach and started our road trip from there. However, if you’re flying in I recommend starting and ending your road trip in Portland. Although it’s in the northwest corner of the state, it’s actually well-positioned for this particular 7 day Oregon road trip. From Portland you can either drive west to Cannon Beach or go east to Columbia River Gorge and do this 7 day Oregon itinerary in reverse.

If you’re planning to do a longer road trip and explore Eastern Oregon as well, I would suggest flying into Portland and out of Bend. This way you don’t have to drive all the way back to Portland.

How to get to Oregon

If you live in British Columbia, Washington or Northern California, you could drive all the way or fly into Portland and rent a car. We looked into both options but it worked out much cheaper for us to hire the car from Vancouver and drive down (we saved $300).

For those coming from further away, I’d recommend flying into Portland and renting a car . I always use Skyscanner to find reasonable rates on flights and use Auto Europe for car rentals as they have great rates.

Do you need to rent a car for this 7-day Oregon road trip itinerary?

You will definitely need to hire a car for this road trip! If you’re flying into Portland International Airport you can pick up your hire car from the airport. Make sure you book in advance to get the best price.

Alternatively, you could rent a campervan instead for this 7 day Oregon road trip. Outdoorsy is the world’s largest and most trusted RV rental market place and have a great selection of adventure vehicles. They take care of liability and collision insurance too so it’s an easy and simple way to book an RV for your trip. My advice is to work out the costs for both options and see what is cheaper. A campervan rental is usually more expensive than a car but you don’t have to pay for hotels which can be pricey.

When is the best time to do this itinerary?

With its diverse landscapes, Oregon offers unique experiences all year-round. That being said, I would recommend doing this 7 day Oregon itinerary in late spring or early autumn.

Spring is a great time to visit Oregon as the wildflowers are starting to appear and the weather is warming up. It’s also peak waterfall season as the snow has just melted so they’re incredibly powerful. There are usually fewer crowds but expect weekends to still be quite busy along the Columbia River Gorge. The downside is that higher elevation hiking trails will still be closed and there can be late snowfalls which lead to road closures. When we went, we couldn’t get down to Trillium Lake because the snow had blocked the entrance.

As with most places, this is peak tourist season so expect crowds and higher prices for accommodation. However, it’s also the best time for hiking, camping, and exploring the famous Crater Lake.

Early autumn is a nice time to visit. Although the waterfalls won’t be very powerful, the fall foliage is very pretty. The weather can be a bit unpredictable but there are fewer crowds and you can get some good deals on accommodation. I would avoid doing this road trip in late autumn as there are often snowfalls which can make travel more difficult.

Winter in Oregon is a magical time and offers great opportunities for skiing, snowboarding and snowshoeing. However, I would personally avoid doing this 7 day Oregon road trip in winter. Some areas on this route may be inaccessible due to snowfall and the mountain passes may even be closed due to winter storms. If you are planning a winter road trip, I would stick to the Oregon coast, Columbia River Gorge, and Silver Falls State Park as the roads in these areas are well-maintained.

Oregon itinerary driving conditions and tips

For the most part, the roads on this 7 day Oregon itinerary are very good. There are a few big pot holes on the road through the Willamette National Forest so watch out for them as some are quite deep. The road to Terwilliger Hot Springs is paved up until the last part where it becomes more rugged.

Some parts of the route are quite remote and you will lose cell coverage. I found that I didn’t have any service in Willamette National Forest and Mt. Hood. It also kept cutting in and out in the Columbia River Gorge. Most of the route is well signed but I recommend downloading offline maps or taking a physical one with you just in case.

Make sure you stock up on groceries before you set off on day 3 and 5 because there aren’t many stores along the way. The same applies for gas. Fill up before you start the drive through Willamette National Forest and Mt. Hood.

7 DAY OREGON ROAD TRIP ITINERARY

This is quite a jam-packed itinerary so you’ll need to get up quite early each day to account for the long drives in-between some of the stops.

OREGON ROAD TRIP DAY 1: TRAVEL TO CANNON BEACH

If you’re flying into Portland and hiring a car, it’s a relatively straight forward drive to Cannon Beach. Once you get through Portland, you’ll pick up Highway 26 west to Cannon Beach for 73 miles. At the end of this highway, you’ll merge onto Highway 101 (the Oregon Coast Highway) which will take you to Cannon Beach.

The whole drive from Portland takes around 1 hour 40 minutes. Although today is most likely a travel day, depending on what time you arrive, you may be able to catch sunset on Cannon Beach.

Where to stay in Cannon Beach

There are some lovely places to stay in Cannon Beach, from oceanfront hotels to guest houses and campgrounds. Here are my top picks:

Tolovana Inn: We stayed here and I can’t recommend it enough! It’s right on the beach but as it’s a bit further down it’s more affordable than other oceanfront hotels. The staff were so helpful and the rooms were modern and so comfortable. In the morning, we walked out of the hotel and straight onto the beach. It was such good value for money. Check prices >
Surfsand Resort: This is another oceanfront hotel but it is closer to the haystack so it’s more expensive than Tolovana Inn. If you’re celebrating a special occasion then have a look at their ocean view rooms. Check prices >
Wright’s for Camping: This is a great option if you’re planning to drive and camp. It’s a family-run campground offering affordable camping close to the beach. The campground is only open from May to October. Check prices >

7 Day Oregon Road Trip Itinerary - Cannon Beach

OREGON ROAD TRIP DAY 2: CANNON BEACH TO LAKESIDE

Wake up early and get ready for a busy day of exploring beaches and sand dunes along the Oregon coast!

First Stop: Cannon Beach

If the weather is on your side, I recommend getting up early and going for a sunrise walk along Cannon Beach. It’s such a lovely way to wake up and means you’ll get to experience the beach before it gets too busy. When we went, sunrise was at 7.15am and we were two of the only people on the beach. Watching the sun light up the famous Haystack Rock was incredible.

If you love photography, walk up the steps which are opposite the Haystack Rock (leading up to the houses and beachfront hotels). This will give you a lovely view looking down at the Haystack Rock. It’s a classic view so you’ve probably seen it on Instagram but it really is worth the hype.

After you’ve finished walking along the beach, wander into the town and grab some breakfast. Cannon Beach Bakery and Lazy Susan Café are great options. The town itself is very quaint so it’s worth popping into a few of the local stores.

Second Stop: Ecola State Park

Driving time: 11 mins (4.6 km/ 2.9 miles)

The next stop is Ecola State Park. It’s only a 10 minute drive north of Cannon Beach and is a lovely area to explore. Set in a lush rainforest, Ecola State Park is home to old-growth trees, pristine beaches and stunning coastal views.

There are a number of great hikes in the park, such as Ecola Point to Crescent Beach (1.25 miles) and Clatsop Loop (2.8 miles). Ecola Point to Indian Beach (1.5 miles) is another lovely trail. If you’re short on time (remember you do have a long drive ahead of you!) or don’t fancy hiking too far, you can drive to Ecola Point. From there, it’s a very short walk to the viewing area where you can see Haystack Rock, Cannon Beach and the smaller sea stacks jutting out of the ocean.

You will need an Oregon State Parks pass, Oregon Pacific Coast Passport, or a $5 day-use pass to park and explore the trails. You can purchase the day pass using the machine at the car park.

7 Day Oregon Road Trip Itinerary - Ecola Point

Third Stop: Cape Kiwanda

Driving time: 1 hour 30 mins (106 km/ 66.3 miles)

Now it’s time to head to Pacific City! This area is home to Cape Kiwanda State Natural Area, one of the most beautiful photography spots on the Oregon coast . It’s known for its stunning cliffs, sandy beaches, and rugged beauty. It even has its own version of Cannon Beach’s Haystack Rock which you can see from Pacific City Beach.

There are a lot of amazing places on the way from Cannon Beach to Cape Kiwanda. If you have an extra day I recommend splitting day 2 into two days so you can visit these spots along the way:

Oswald West State Park
Elk Flats Trail

The highlight of Cape Kiwanda is the massive sand dune which separates Pacific City Beach on the south side from McPhillips Beach on the north side. You can climb up to the top for amazing views over both beaches but be warned it is steeper than it looks. Please also pay attention to the signs and do not venture too close to the fragile edges of the cliffs.

If you’re visiting at low tide, you can walk between the sandstone arches on the north side of the cliffs. You can access this area by walking all the way down McPhillips beach towards the sand dune, or by climbing up and over the sand dune from Pacific City Beach. Do not try and access this area when the tide is in as it is incredibly dangerous and you risk getting stranded or caught by sneaker waves. You can check the tide times here .

7 Day Oregon Road Trip Itinerary - Cape Kiwanda

Fourth Stop: Lakeside (Optional)

Driving time: 2 hours 44 mins (200 km/ 124 miles)

We really wanted to see the sand dunes on our 7 day Oregon road trip. There are a lot of different sand dunes along the coast but we wanted to see the larger ones which are located further south near Lakeside. If you’re not worried about seeing them you don’t need to drive all the way down to Lakeside. Instead I would stay overnight in Cape Kiwanda. That way, you can take your time driving from Cannon Beach to Cape Kiwanda and explore some of the other stops I mentioned above on day 2 instead.

If you do want to see the John Dellenback Sand Dunes, Lakeside is a good place to stay overnight. The dunes are only open from 7am to 7pm so it’s unlikely you’ll get there in time on day 2 but you’ll be close by for the next day. I recommend stopping en-route and buying some food for breakfast and lunch for day 3. It’s going to be a long day and you’ll want an early start so having things for breakfast will save you a lot of time.

Where to stay in Lakeside

We actually stayed in Winchester Bay as there weren’t many options available but I wouldn’t recommend the place we stayed (Winchester Bay Inn). Instead, I would suggest staying in Lakeside:

Lakeside Holiday Home: If you’re travelling with a group then this is a great option as it sleeps up to 5 people. It has all the amenities you need including a kitchen, washing machine and dryer, BBQ and Wi-Fi. Check prices >
Seadrift Motel & RV Park: This is a good option if you’re travelling with an RV but it is pretty basic. It’s close to the sand dunes and has the essentials. Check prices >
Best Western Salbasgeon Inn & Suites: If you prefer hotels, your best option is the Best Western in Reedsport. It’s a bit further away but is still only a 15 minute drive to the sand dunes. Check prices >

OREGON ROAD TRIP DAY 3: LAKESIDE TO BEND

Get up and have some breakfast while getting ready for another busy day. Once you’ve fuelled up for the day, it’s time to drive to John Dellenback Sand Dunes. From here, you’ll then drive into central Oregon to explore the Willamette National Forest before heading to Bend for the night. If you haven’t already, I suggest stocking up on food and supplies before you drive through Willamette National Forest. Cell service will be very spotty in this area so you probably won’t have signal for part of today’s drive.

First Stop: John Dellenback Sand Dunes

Driving time: 5 mins (2.9 km/ 1.8 miles)

The John Dellenback Sand Dunes are located in the Oregon Dunes National Recreation Area. These particular sand dunes are the widest stretch of dunes on the Oregon coast so it’s a very unique outdoor experience. What makes them even more special is that they are closed to motorized vehicles. While other areas of the Oregon Dunes National Recreation Area are open to OHVs, this area isn’t so you can walk on them safely.

The best way to explore the dunes is on the John Dellenback Dunes trail head. It’s a 9km loop which takes you through the sand dunes out to the ocean and back but you don’t have to do the whole trail. We knew we had a long day ahead of us so we just did the first couple of kilometres and then turned back.

You need to pay the $5 day-use fee to park here and hike the trail. Despite reading lots of blog posts that said you had to pay in cash (and rushing around trying to find an ATM), you can pay online using your phone. When you arrive, head to the information board and you’ll see the QR code. You can scan that and then follow instructions to get your day pass. Northwest Forest Passes and Interagency Passes are also accepted.

The trail starts from the parking lot and takes you through the coastal forest. After about half a mile, you’ll emerge from the forest onto the sand dunes. Go left and hike up the large sand dune. From here, you’ll get amazing panoramic views over the dune landscape. You can continue on to the ocean or just stay here and take in the sand formations like we did.

7 Day Oregon Road Trip Itinerary - John Dellenback Sand Dunes

Second Stop: Terwilliger Hot Springs

Driving time: 2 hours 49 mins (244 km/ 152 miles)

After you’ve finished exploring the sand dunes, it’s time to start the long drive up to Willamette National Forest. I recommend stopping in Eugene (approximately 1 hour 45 mins driving time) to get some lunch and break up the journey.

From Eugene, you’ll take Highway 126 (also known as the McKenzie Highway into the forest. After about 50 minutes, you’ll turn right onto Cougar Dam Road and then right again at the next junction. Keep driving along this road until you reach Cougar Reservoir where the road splits. Go right and keep driving until you reach the parking lot for Terwilliger Springs. This part of the drive can be a bit bumpy so watch out for pot holes.

Terwilliger Hot Springs (also known as Cougar Hot Springs) is a natural hot spring located in the forest. It’s open from sunrise until sundown each day and gets very busy so don’t expect to have this place to yourself unless you’re able to go first thing in the morning! To get to the hot springs, you have to hike an easy 0.5 mile trail through the forest. The entrance fee costs $10 per person for 2 hours and is payable by cash or card at the trailhead which is often manned.

There are a few different hot pools with varying temperatures. The upper pool is the hottest but that makes it the most popular so you may want to try some of the lower pools instead. In the US, hot springs are clothing optional so expect some nudity. Be respectful if you’re taking photos and read up on hot spring etiquette before going.

7 Day Oregon Itinerary - Terwilliger Hot Springs

Third Stop: Koosah and Sahalie Falls

Driving time: 41 mins (50.8 km/ 31.6 miles)

Once you’ve finished soaking, head back to the car and drive back up to Highway 126. Turn right onto the highway and continue driving for about 25 minutes until you see the sign Sahalie Falls on the left hand side. There is a small parking area along the side of the road. You’ll need to do a U-Turn to park there so just be careful as cars drive quite quickly along this highway.

Sahalie and Koosah are two beautiful waterfalls which are located in the Willamette National Forest. The 2.2 mile Waterfalls Loop trail offers incredible views of both waterfalls, as well as the McKenzie River rushing through the canyons. I don’t think I’ve ever seen such a blue river before! If you don’t want to do the full hike, you can just walk 5 minutes from the car to Sahalie Falls lookout instead.

The trail is well-maintained but if you’re doing this 7 day Oregon road trip in spring, I would pack some micro-spikes. There is usually a lot of snow in this area and although the trail will be packed down it can be very icy.

7 Day Oregon Road Trip Itinerary - Koosah and Sahalie Falls

Fourth Stop: Bend

Driving time: 1 hour 8 mins (91.4 km/ 56.8 miles)

Once you’ve finished at the waterfalls, it’s time to drive to Bend. It should take about an hour but you can always stop in the town of Sisters on the way if you need gas, food or a rest break. You’ll probably arrive in the evening so I recommend checking into your hotel and going out for some food. Tomorrow, you’ll have a more relaxing day and will be able to explore Bend properly.

Where to stay in Bend

There are plenty of options to choose from in Bend. Here are a few ones that I’d recommend:

The Riverhouse on the Deschutes: Located just north of the town centre on the river, the Riverhouse is a great place to stay if you’re visiting Bend and want somewhere peaceful to relax. We stayed here on our 7 day Oregon road trip and I can’t recommend it enough. Check prices >
Campfire Hotel: This boutique hotel is a great affordable option if you’re travelling on a budget. The rooms have everything you need and there is also an outdoor pool, hot tub and fire pit. If you’re looking for a more sociable atmosphere then this is a good place to stay. C heck prices >
Springhill Suites Bend: Located in the Old Mill District, Springhill Suites is another great place to stay while visiting Bend. It’s also walking distance to the town centre (15 minutes) so you can easily explore on foot and not worry about driving or parking. Check prices >

OREGON ROAD TRIP DAY 4: BEND

After a busy few days of driving, today will be a much slower day so you can relax and rest before hitting the road again tomorrow. Known for its outdoor recreation, craft beer scene, and vibrant arts culture, Bend is a great town to explore. It offers ample opportunities for hiking, biking, skiing, and river rafting depending on the time of year you visit. Here are a few fun things to do in Bend:

Explore the town

Bend’s downtown area is bustling with unique shops, art galleries, and local eateries serving up delicious farm-to-table cuisine. Explore the town centre and then wander down to Drake Park and walk along the river. Check out the Old Mill District and grab a coffee from Sisters Coffee.

Try local beers

Bend is known for its microbreweries, making it a popular place for beer lovers. Deschutes Brewery is renowned for its iconic Black Butte Porter and offers tours and tastings. For something a bit different, try Boneyard Beer which has lots of innovative brews. 10 Barrel Brewing Co. is another great spot offering a lively atmosphere and wide selection of beers. Other notable breweries include Silver Moon Brewing and Bend Brewing Co.

Hike up Pilot Butte

This large, cinder cone is visible from almost anywhere in town. Formed over 190,000 years ago from a volcanic eruption, Pilot Butte offers panoramic views of Bend and the surrounding Oregon landscape. It’s a 2 mile round trip and usually takes about an hour to hike there and back. If the weather is on your side, aim to hike up Pilot Butte for sunset and enjoy 360 degree views in golden hour.

Visit Tumalo Falls

Located about 20 miles outside of Bend, Tumalo Falls is a stunning, 89-foot tall waterfall. To get there, take Skyliners Road from Bend and follow the signs. The falls are visible from the parking lot and a short hike will take you down to the base of the falls. For a longer hike, take the Tumalo Falls Trail, a 7.5 mile loop that offers beautiful views of the waterfall and surrounding wilderness. The trail is moderately challenging and you’ll enjoy lush forests, cascading creeks, and panoramic vistas on the way.

Check out Mount Bachelor

Mount Bachelor is a stratovolcano in the Cascade Range of Central Oregon. In winter, it offers world-class skiing and snowboarding on its expansive slopes. It’s also a great spot for snowshoeing, snow tubing and dog sledding. In summer, the mountain transforms into a playground for hiking and mountain biking.

For more things to do in Bend, check out Visit Bend’s website.

OREGON ROAD TRIP DAY 5: BEND TO HOOD RIVER

Today is going to be quite the adventure! If the weather is nice, get up early, grab some breakfast and head to Smith Rock State Park for a sunrise/ early morning hike. Consider packing some breakfast to eat on the trail and some food for the drive through Mt. Hood as there aren’t a lot of places to stop.

First Stop: Smith Rock State Park

Driving time: 30 mins (42 km/ 26 miles)

Located just 30 minutes from Bend, Smith Rock State Park is one of the most unique spots on this 7 day Oregon road trip. The park is one of the 7 wonders of Oregon and boasts towering rock formations carved by the Crooked River, creating a dramatic landscape of cliffs and canyons. The park’s unique geology makes it a popular spot for rock climbing and hiking.

Important information about Smith Rock State Park

You need to pay the $5 day-use fee to park here and hike the trail. When you arrive, head to the information board and you’ll find the pay machine.

There are rattlesnakes in some parts of the park, particularly near the river, so keep your eyes peeled. In summer, they will hide under rocks to keep cool so just be mindful. I also recommend reading up on trails before you hike and checking in with the visitor centre as people report snake sightings to them. Seek medical attention immediately if you are bitten.

The best way to experience the park is to do one of the hiking trails. Rim Rock Trail (0.5 miles) is a great easy hiking option and circles the ridge of the park. You’ll get sweeping views and the trail is relatively flat so it’s a good one for kids. Another good option is Canyon Trail (1.5 miles) which takes you down to the river.

If you’re a keen hiker and are up for something more challenging, I highly recommend the Misery Ridge and River Trail (4 miles). It is an uphill grind but it will take you up to Misery Ridge where you’ll get panoramic views over the park and out to the Cascade Mountains. This is a great hike to do for sunrise or sunset depending on when you visit.

Best hikes in Bend at Smith Rock State Park

Second Stop: Trillium Lake (Seasonal)

Driving time: 1 hour 44 mins (137 km/ 85.3 miles)

Head north on Highway 97 for about 10 minutes and then merge onto Highway 26. This will take you all the way to Mount Hood National Forest. It’s a beautiful drive through dense forests and towering peaks. Home to the iconic Mount Hood, the highest point in Oregon, this area is a popular spot for hiking, camping, fishing and skiing. On this 7 day Oregon road trip, you’ll only have time to explore Trillium Lake. However, if you have more time you could add on an extra day and explore more of Mount Hood.

Trillium Lake has a beautiful view of Mount Hood and is incredibly picturesque. This is a great place to have lunch and stretch your legs. There are vault toilets and picnic tables. If you feel like it, you can also do the easy 2-mile Trillium Shoreline Look Trail.

If you’re travelling in spring, be aware that the road may not be accessible. When we went in March there was a lot of snow along the highway and it was blocking the entrance down to Trillium Lake. We weren’t able to make it down to the lake even though we had a SUV. Before starting your trip to Mount Hood, check the National Weather Service’s website for up-to-date information on current snow conditions.

Third Stop: Hood River

Driving time: 59 mins (68 km/ 42.3 miles)

Now it’s time to head north to Hood River! This will be your final destination for the day, but if you’re making good time, feel free to stop at any other points of interest along the way.

Hood River is a picturesque city located on the Columbia River and is renowned for windsurfing, kiteboarding, hiking and mountain biking. Aim to arrive here by late afternoon so that you can explore the area before dinner. The Indian Creek Trail and Hood River Waterfront Trail are both lovely walks. Another great option is Panorama Point. This park is handicapped-accessible. You can drive up to this viewpoint and enjoy panoramic views of Hood River Valley, including Mount Hood and the numerous wineries and orchards.

There are also plenty of vineyards and tasting rooms such as Phelps Creek Vineyards, Cathedral Ridge Winery, and Hood Crest Winery. For a fun evening activity, book a wine and bike tour with MountNbarreL .

If you’re doing this 7 day Oregon road trip in June or July, don’t miss the Hood River Lavender Farms. They grow and produce local and organic lavender products such as essential oils and soaps. The lavender usually blooms in late June and you can pick your own lavender for $10.

Hood River is also home to Mount Hood Railroad . This is one of the best attractions in Hood River for kids and adults alike. You can take the hour-long train ride from downtown into Hood River Valley. It’s a scenic journey through the Columbia River Gorge past orchards and vineyards.

Where to stay in Hood River

Hood River has a range of accommodation options. Here are a few recommendations:

Hood River Hotel: This historic hotel is one of the oldest spots in Hood River. Located in the centre of downtown, Hood River Hotel is a great base for exploring the local restaurants, breweries and wineries. They’re actually the sister hotel of Campfire Hotel in Bend so you may be able to get a discount if you book both. Check prices >
Sunset Motel Hood River: This is a great option if you’re travelling on a budget. Sunset Motel Hood River is a bit further from the town but is located close to the highway which makes it an ideal place to stay. Check prices >
Tucker Park Campground: If you’re looking to camp, Tucker Park Campground is a good option. All campsites at Tucker Park are available on a first-come, first-served basis between May 1 and October 31. The campground is closed between November 1 and April 30. Check prices >

View of Mount Hood from the Columbia River

OREGON ROAD TRIP DAY 6: HOOD RIVER TO PORTLAND

You’ll be exploring one of my favourite parts of Oregon today – the Columbia River Gorge. Spanning over 80 miles, Columbia River Gorge serves as a natural boundary between Oregon and Washington. It’s another of Oregon’s 7 wonders and for a good reason! The Columbia River Gorge is home to unique geological features and scenic vistas. With over 90 waterfalls scattered throughout the area, the Gorge is often referred to as the ‘waterfall wonderland of the Pacific Northwest’.

There are so many incredible waterfalls on today’s drive along the I-84. Some are very accessible (viewpoints close to the parking lot) while others require you to hike in. You can stop at as many as you like but here are my suggestions based on our own 7 day Oregon itinerary.

Waterfall permits

If you’re visiting between May and September, you will need a timed permit to visit most of these waterfalls. You can find more information here .

First Stop: Wahcella Falls

Driving time: 25 mins (37 km/ 23.3 miles)

This was probably my favourite waterfall in the Columbia River Gorge. The short 1.9 mile out-and-back hike leads you through the lush canyon to the two-tiered waterfall. It’s a fun and scenic hike but it can be quite slippery if there has been a lot of rain so make sure you have shoes with good grip. It costs $5 USD to visit. You can pay online by scanning the QR code once you arrive at the car park.

Oregon road trip itinerary - Wahclella Falls in the Columbia River Gorge

Second Stop: Multnomah Falls

Driving time: 11 mins (14.8 km/ 9.2 miles)

Head back onto the Historic Columbia River Highway and drive 10 minutes west to Multnomah Falls. This is one of the most accessible waterfalls in Columbia River Gorge so it can get quite crowded. The parking lot can fill up quickly in the summer months and on weekends so you may have to drive to another waterfall and try again later.

From the car park, cross over the road and the viewing platform is straight ahead of you. This two tiered waterfall is an iconic sight and is the tallest waterfall in Oregon. If you want a different perspective you can hike 0.2 miles up to the Benson Bridge or 1.2 miles to the top of the falls. We decided to just enjoy the view from the main viewing area as we wanted to see quite a few different waterfalls.

Oregon road trip itinerary - Multnomah Falls in the Columbia River Gorge

Third Stop: Latourell Falls

Driving time: 12 mins (9.5 km/ 5.9 miles)

The final waterfall on today’s list is Latourell Falls. You can walk down to the base of the waterfall (less than 5 mins) or you can opt to do the 2.4 mile round trip hike to see the upper falls as well. At the base of the waterfall there is a lovely bridge which is great for photos with the waterfall in the background. This particular waterfall can be very busy as it’s one of the closest ones to Portland so be prepared for crowds in the summer and at weekends.

The best things to do on an Oregon road trip

Fourth Stop: Portland

Once you’ve finished exploring the Columbia River Gorge, it’s time to drive back towards Portland. If you’re flying out of Portland, it makes sense to stay here overnight and explore a bit of Portland before you leave. However, if you’re travelling back to Vancouver or Washington, you might want to drive further north and stay closer to Seattle. We decided not to stay in Portland and instead continue up to Olympia for two reasons. Firstly, accommodation was a lot cheaper and secondly, we wanted to shorten the long drive back to Vancouver. It’s completely up to you and will depend on where you’re travelling back to.

Where to stay in Portland

If you decide to stay overnight in Portland, here are a few hotel options:

The Mark Spencer Hotel: Located in Portland’s Pearl District, this boutique hotel is just steps from all that Downtown Portland has to offer. Check prices >
Courtyard by Marriott Portland City Center: This hotel is also in the Pearl District. It’s on the pricier side but has fantastic amenities and is also pet friendly. Check prices >
Econo Lodge City Center: Located further south, this is a great budget option. It’s close to Portland State University and is good value for money. Check prices >

OREGON ROAD TRIP DAY 7: TRAVEL HOME

It’s time to head home! Depending on where you’re travelling back to, you could explore Portland in the morning before your flight home. If you’re driving back to Washington or Vancouver, you could stop in Seattle or explore some beautiful spots in Washington, such as Snohomish, Bellingham or Chuckanut. If you have a few extra days, I highly recommend extending your road trip and visiting Olympic National Park in Washington. With ancient rainforests, rugged coastal beaches, and unique ecosystems, it’s an amazing place to explore.

MORE THINGS TO DO ON AN OREGON ROAD TRIP

This 7 day Oregon road trip will give you a taste of the state’s epic scenery. If you have more time and want to see more of Oregon, you could continue on to some of the below destinations:

Silver Falls State Park
Umpqua National Forest (Toketee Falls and Umpqua Hot Springs)
Samuel H. Boardman State Scenic Corridor
Crater Lake National Park

PLANNING A 7 DAY OREGON ROAD TRIP: FINAL THOUGHTS

Oregon really does have it all and I can’t wait to go back and explore more of this state. I hope this guide helps you plan your own Oregon road trip. If you have any questions, please drop them in the comments and I’ll do my best to answer them!

Where to explore next?

If you’re looking for more North America travel inspiration, have a look at these guides:

A complete guide to Capitol Reef National Park
Exploring Zion and Bryce Canyon: An epic 3-day road trip itinerary
How to spend a weekend in Bryce Canyon

British Columbia

7 Amazing places to visit on Vancouver Island
North Vancouver Island: An amazing 4-day road trip itinerary
The ultimate Vancouver to Banff road trip itinerary
The Best of Banff: The complete 4-day itinerary
How to explore Banff and Jasper without a car
Driving the Icefields Parkway: The stops you can’t miss

Love from Steph

Save for later.

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A girl Kayaking at Trillium Lake which overlooks the Mt. Hood Mountain

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The Perfect Oregon Road Trip Itinerary – 7 or 10 days

Last updated on September 25th, 2023 at 01:38 pm

Oregon (pronounced “Ore-gun”, not “Ore-gone”!) is often overshadowed by its extremely popular neighboring state of California in the US. But if you are looking for a road less traveled then you have to take an Oregon road trip. In this blog post, we will share our detailed itinerary including what to see, do, and where to stay.

Below is a map of the route we took on this trip, click here to go to Google Maps. We drove across the state in a clockwise direction but you can do the same in an anti-clockwise direction as well. If you remember we did a similar 7-day road trip in Iceland and trust me when I say that our Oregon road trip was just as adventurous. Don’t forget to check out our post on waterfalls near Portland for more incredible inspiration.

FUN FACT: Oregon is the only other state in the US after New Jersey to have assistants at gas stations to fill gas in your car.

How Many Days Do You Need for an Oregon Road Trip?

We were able to make this a total of the 10-day trip including travel time. If you follow our Oregon itinerary you will have plenty of time to go on hikes, take wine tours, and relax on this road trip.

You can easily make this a 7-day road trip and we’ll tell you how in the modified itinerary below. However, if you have less than 7-days then I suggest visiting only Portland, Columbia River Gorge, Mt. Hood region, & Cannon Beach from the itinerary below.

Disclaimer: This post contains affiliate links.

Related Read: SF to LA – An ultimate west coast road trip guide

Starting point

We flew into Portland and spend 2 days in the city before starting our road trip. TIP: You do not need a car in Portland city so save yourselves some cash by renting a car the day you hit the road.

Portland would be our recommendation as a starting point for all those who are flying into Oregon. For those who are driving from the South i.e. California, the best starting point for you would be either the coast or Crater lake in this loop.

Oregon Road Trip Itinerary

Below is our detailed itinerary is broken out by each day. If you want to do a 7-day road trip then we have listed where it makes the most sense to skip things.

Day 1 & 2 – Portland

After you land in Portland spend 2 days in this funky city. We not only explored the city landmarks but in reality spend the entire weekend food binging in Portland. TIP: If you want to make this a 7-day road trip then spend just 1 day in Portland.

We will be writing a separate post on what to do on a weekend in Portland. But to highlight a few things –

Eat your heart out in the food capital on the west coast. From food trucks to delicious worldwide cuisines all around town you’re going to return with some additional baggage on your body.
Check out the largest bookstore in the world – Powell’s Bookstore
Must eat doughnuts (try both Bluestar & Vodoo doughnuts to give your own verdict no matter what the locals say)
Take a walking city tour or a Segway tour to learn more about the city
Check out the Japanese Garden

ACCOMMODATION: It usually nice if you stay in either downtown or the pearl district so you’re walking distance away from all the things –

Hilton Portland Downtown or the Hampton Inn Pearl District
The Bidwell Marriott Portland or the Courtyard Marriott City Center

More Places to Stay in Portland, Oregon

Harlow Hotel

Inn at Northrup Station

Day 3 – Columbia River Gorge Waterfalls & wineries

Fasten your seatbelts and drive to the Columbia River Gorge which is only 30 minutes away from Portland. If you start driving early in the morning, you’ll easily be able to cover all the stopovers mentioned below in that order. For more details, read our in-depth blog post on Columbia Gorge road trip .

Portland Women’s Forum vista point (has the best sunrise view if there are no wildfire smoke)
Latourell Falls (add a short 2.4 mile hike here)
Multnomah Falls
Bridal Veil Falls (add a short 1.2 mile hike here)
Starvation Creek Falls
Wineries tour in Mt. Hood/Gorge

ACCOMMODATION: Spend the night in White Salmon, WA or Hood River, OR

Find fun things to do in Oregon during your road trip!

Panoramic view of columbia river gorge from Portland Women's Forum

Day 4 – Explore Mt. Hood Region

We spent 2 nights in Mt. Hood region which gave us the time to not only explore but also relax in the most gorgeous setting. There are a ton of outdoor activities to do here so spending only 1 day would be an injustice to this region. We have broken down the activities by each day for you –

Explore Hood River town which is known as the world’s kite surfing capital, perhaps indulge in some water activity or grab lunch here
The Gorge White House makes for a great stop for Apple cider tasting and fresh fruit & flower farm
If you happen to visit in spring don’t forget to check out the “ fruit loop ” trails for spring blossoming trees .
Drive to the historic Timberline Lodge and either take the chair lift to get to the summit or if you are up for an adventure there are tons of hiking trails behind the lodge. We did a section of the zigzag overlook trail which starts at the lodge parking area. Ask the lodge visitor center for more info on trails. Enjoy a nice early dinner or a cup of coffee with a view.
If you are not up for visiting the lodge then consider hiking the Mirror Lake loop trail that afternoon. We skipped the mirror lake loop.
Return to Government Camp for dinner unless you are staying back at Timberline Lodge.

A couple walking the trail to Mt. Hood mountain which is behind the Timberline lodge

ACCOMMODATION: Spend the night in Mt. Hood region. We stayed in a gorgeous farmhouse surrounded by apple & pear orchards booked through Airbnb . Your other best option is to stay at the historic Timberline Lodge or hotels in Government Camp , a small town in Mt. Hood region.

Day 5 – Explore Mt. Hood Region

Here’s what to do on your second day in Mt. Hood region –

Hit the Tamanawas Falls hiking trail in the morning (alternatively, you can do the Mirror Lake loop). Tamanawas trail is amazing, take our word for it.
Have your lunch at Tamanawas Falls. Pack your lunch with you so you can eat with the waterfall views at the end of the hike.
After lunch head to Trillium Lake in the afternoon. Walk along the lake trail or rent a kayak and enjoy the serene Mt Hood view from the water. TIP: Book your kayak rental in Govt Camp as there are no rental facilities at Trillium lake. The rental company will bring your kayak to the lake area. Don’t miss the sunset at Lake Trillium! TIP: Bring mosquito spray, there are like a thousand of them here. You can also rent campgrounds at Trillium lake if you want to camp in this area.

ACCOMMODATION: We stayed back at the same farmhouse Airbnb with the perfect view of Mt. Hood. Your other best option is to stay at the historic Timberline Lodge or hotels in Government Camp , a small town in Mt. Hood region.

A girl walking through wooden bridge over a river on a hike to tamanawas falls in Oregon

Day 6 – Smith Rock State Park, Painted Hills & 3 Sisters

As you drive south from Mt. Hood, take a day to explore the desert region of Oregon. You’d be surprised to know that a big part of Oregon is, in fact, desert land. What was really fascinating to us was that our families in India instantly knew about Oregon out of all the places. They were the ones to tell us about Rajneeshpuram. FACT: Rajneeshpuram (from ‘Wild Wild Country’ series on Netflix) was not too far from this part of Oregon.

TIP: For a 7-day Oregon road trip, skip this section and head straight to Crater Lake from Mt. Hood.

Stop at Smith Rock State Park as you drive south from Mt. Hood region. and enjoy the gorgeous scenery.
Drive about 2 hours east to see the Painted Hills which are in the deep end of the Oregonian desert.
Reach Bend and head to Summit Park for a great view of the 3 Sisters volcano peaks .
If you want to get a better view of 3 sisters then drive 30 mins from Bend to Dutchman Flat Sno Park in Deschutes National Forest.

ACCOMMODATION: Spend the night in Bend, OR .

Where to Stay in Bend, Oregon

Element Bend

Campfire Hotel

Holiday Inn Express & Suites

colorful hills on the dessert side of eastern Oregon in USA

Day 7 – Crater Lake National Park

Crater Lake National Park is about 2 hours away from Bend or about 4 hours from Govt Camp. If you leave early in the morning, you can reach Crater Lake just in time to drive around the rim and see the following viewpoints & sneak in one easy hike.

Pick and choose your favorite spots to see in Crater Lake National Park , below are a few that we recommend –

Sinnott Memorial Outlook at Rim Visitor Center
Sun Notch (0.8 miles easy hike with views of Phantom Ship)
Phantom ship overlook
Discovery Point (2 miles)
Watchman Peak (1.6 miles moderate steep hike)
Pumice castle overlook,
Cloudcap overlook,
Vidae Falls
Pinnacles Overlook.

ACCOMMODATION: Spend the night in Crater Lake Lodge or campgrounds in the park . If you don’t get a reservation in either of these then consider staying in Fort Klamath or Chemult or Chiloquin which are small towns near Crater Lake. TIP: If you stay at Crater Lake Lodge, then don’t miss the splendid sunset from the lobby’s back patio.

View of crater lake blocked from the thick smoke cover of wildfires in the neighboring region of the National Park

PLEASE NOTE: The Crater Lake itinerary was a part of our original plan until west coast wildfires & smoke completely ruined the experience. When we arrived at Crater Lake National Park, it became really difficult to breathe without inhaling the fumes. Not to mention, the visibility of the Lake was near zero. We had booked a campground for the night but for good reasons we decided to turn around. As a backup plan, we headed to spend more time on the Oregon coast. PRO TIP: Watch out for wildfire and smoke reports in Oregon before you head here!

Day 8 – Umpqua National Forest & drive to Eugene

Next morning stop by the Crater Lake vista points that you might’ve missed on the previous day. On your way to the coast of Oregon, you must take a pitstop at Umpqua National Forest for a bonus waterfall & hidden hot springs.

Drive around Crater Lake in the morning to cover any missed vista points from the previous day.
Hike the Toketee Waterfall trail in Umpqua National Forest as you exit Crater Lake. It’s an easy 0.8 miles round trip hike to the gorgeous waterfalls as you can see in our photos.
If you enjoy natural hot springs , then as you exit from Toketee waterfalls take a left and head to Umpqua Hot Springs . There is a $5/vehicle charge to park at the hot springs. Clothing is not enforced here so consider yourself forewarned. In full disclosure, we did not visit the hot springs due to a lack of time.
Drive to Eugene from Toketee Falls should take around 2.30 hrs.

ACCOMMODATION: Spend the night in Eugene, OR .

Where to Stay in Eugene, Oregon

Comfort Suites Eugene

Maverick Hotel

Graduate Eugene

toketee falls overlook in Oregon with lush green vegetation around it

Day 9: Oregon Coast road trip

The next morning we headed to Florence from Eugene where we started our Oregon coast drive. The coastal drive takes you on Highway 101 which, in fact, is a continuation of California’s coast to Oregon’s.

Given that we just had one day set aside for this Oregon coast road trip, we only stopped at the vista points mentioned below in bold. We’ve listed some additional awesome pit stops along the way if you have more time.

Drive past Florence
Heceta Head Lighthouse Scenic Viewpoint (There is a B&B at this lighthouse now) or stop at Sea Lion vista point to see the lighthouse from a distance.
Cape Perpetua Overlook (Thor’s Well is another stop before turning right to Cape Perpetua overlook)
Yachats (stop by for a drink or early lunch)
Newport (If you skip Yachats then stop here for lunch)
Devil’s punchbowl and Otter Rock
Tillamook (stop by at the cheese factory or the Tillamook ice-creamery)
Cannon Beach, get here before sunset to watch the magic unfold

ACCOMMODATION: Spend the night in Cannon Beach, OR .

A girl standing at the vista point of Oregon Coastal view

Day 10: Lewis & Clark National Park OR Evergreen Aviation Museum

We took a red-eye back to the east coast since we wanted to squeeze every second of our last day. TIP: For a 7-day Oregon road trip, skip this part and fly out on your last day.

We visited the Evergreen Aviation & Space Museum in the morning but you can choose to visit the Lewis & Clark National Park near Cannon Beach to get an insight into expeditions that were an integral part of US history.
Head back to Portland to grab an early dinner before heading out to the airport for an evening flight.

Aircraft Museum in Oregon dispalying airplanes from US airforce and navy

Phew, another long guide, isn’t it? But there is so much to see & do here that you have to plan it right and we’ve to give all the right info to do so. And by the way, if Oregon wasn’t on your list, we sure hope it is now!

If you liked this extensive Oregon road trip planning guide then don’t forget to share it along with family & friends.

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23 comments on “ the perfect oregon road trip itinerary – 7 or 10 days ”.

Such a detailed guide. Thanks for sharing! Perhaps this fall my family and I will go to the Oregon. Awesome photos!

Thanks Michael. Hopefully the fires will be in control by then and the smoke out of OR skies. This year the wildfires have been terrible for Oregon.

Wow you really packed a lot in to tour trip. As someone who lives in Oregon, this is a great post. Come back soon!

We would love to!!! 😀

Wow! Mind blowing and eye catching photography. All places are just awesome. Hope to trip to those places in the near future. Stunning! You must (please) take me there when I visit. Thanks for sharing such a beautiful place.

You are most welcome and hope you visit Oregon someday 🙂

We did a Northern California road trip in June last year and did a tiny bit of Oregon so that we could try some of the wineries up there. I wish we’d done more of Oregon because it looks amazing and I’m filing your post for our next trip!

There’s always a next time 🙂

I’ve never visited the northwest USA but I really have to get there asap, this road trip looks amazing! 🙂

Yeah the Pacific Northwest is truly magical 🙂

Wow, great itinerary! I hope to come back to USA next year and was just looking into California and neighboring states for potential road trip ideas. Oregon looks an idea place to visit! Love the nature and national parks

Oh yes definitely visit OR if you are coming to CA, you will love it! 🙂

Oregon is such a beautiful state, I can’t wait to spend more time there. This looks like a really good way to see a lot of the state in one well, a great itinerary. I live in Vancouver Canada so this is such a doable trip for me

Oh yeah, definitely easily doable from Vancouver. I believe there is an easy train ride from Seattle to Portland, wonder if there is a train from Vancouver to Portland as well?!

I love a good road trip! Thanks for sharing these great places in Oregon 🙂

Most welcome! There’s nothing like sharing cool places to do a great road trip. 😀

We did a similar trip a few years ago, but looks like we missed the Umpqua National Forest. Oh well! Looks like we just need to head back.☺️ Thanks for the post!

You’ve got to leave something out to return back to such amazing places right?! 😉

I had no idea Oregon was this beautiful! I love the suggestion of seeing the state through a road trip, definitely saving for later 🙂

Yeah, this is one of the perfect States to visit in one road trip 🙂

There is obviously plenty to do in Oregon. My personal goals for almost any trip is to do lots of hiking and visit lots of breweries and wineries. I didn’t know that you could have your gas filled by station attendants there. I think I might plan a trip there for that alone. It would be so cool!

It’s great to learn that you should stay downtown when going on a trip to Portland. My wife and I are looking to travel to Oregon soon and we were wondering where we should stay at in the state. I’ll be sure to let my wife know that we can stay in downtown Portland.

Oh yes, Portland is so close to a lot of nature in Oregon. However, if you want to do a road trip around the entire State then as mentioned above you might have to pick other cities for overnight stay esp when going down south or east.

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The best places to visit in Oregon: 5 exciting itineraries

I f you’re planning a visit to Oregon, it can be difficult to choose the right Oregon itinerary. Located in the Pacific Northwest, Oregon is a beautiful, yet incredibly diverse state. Within one day, you can travel from sea to mountains, from rain forest to high desert.

So with such an abundance of natural beauty to experience, you’ll want to choose an itinerary that will make the most of your time. Here are five Oregon itineraries that will help you do just that.

These five itineraries will explore Oregon’s seven wonders, the Oregon Coast, the Oregon Outback, Portland Oregon, and part of the Oregon Trail. These are the best places to visit in Oregon.

Oregon Wonders Itinerary

The Oregon Wonders itinerary covers Oregon’s wide range of climates, allowing you to experience a little of everything Oregon has to offer. This loop starts and ends in Portland.

First, see Oregon’s temperate rain forest as you drive east from Portland, through the Columbia River Gorge towards Multnomah Falls , the tallest waterfall in Oregon.

Then continue east to the beautiful Mt. Hood . Go for a hike at Mt. Hood, like to Ramona Falls. Or visit Timberline Lodge, where The Shining was filmed.

Next, travel further East to experience Oregon’s high desert. In the Wallowa Mountains , take a gondola ride from Wallowa Lake Village to the top of Mt. Howard, where you can see to the next state over.

Admire the warm colors of the Painted Hills , and go hiking or rock climbing at Smith Rock State Park .

Then, visit Oregon’s only national park, Crater Lake National Park . And finally, drive along the Oregon Coast for stunning views of the Pacific Ocean before returning to Portland.

The best time of year to plan this road trip is typically in July, August, or September, when the roads are open in Crater Lake.

However, July and August tend to be particularly hot months in Smith Rock. So it’s best to plan for an early morning hike here before the heat of the day.

Plan to spend at least ten days for this road trip. This will allow time to experience each of the Seven Wonders of Oregon , plus some travel time.

Oregon Coast Itinerary

This itinerary takes you along Oregon’s ruggedly beautiful coastline. Highway 101 , also known as the Pacific Coast Highway , runs for 363 miles down Oregon’s western most border.

This Oregon Coast road trip starts in Astoria and ends in Brookings, Oregon’s northern and southern most cities.

Along the way you’ll see 3 haystack rocks, in Cannon Beach (the rock filmed in The Goonies), Pacific City , and Bandon. You’ll visit two aquariums, in Seaside and Newport, where Keiko once lived. And visit 7 of Oregon’s 11 lighthouses.

Also, explore a shipwreck near Astoria, a ghost forest in Neskowin, and a sea lion cave near Florence. Plus, go whale watching from the world’s smallest bay in Depot Bay. Then, learn about our impact on the oceans at the Washed Ashore Art Gallery in Bandon.

And all along the way, enjoy delicious food. Many restaurants on the coast serve fresh seafood and warm clam chowder with stunning views of the ocean.

But be sure to eat at the Pronto Pup in Rockaway Beach , where the corn dog was invented! Then enjoy ice cream and squeaky cheese (cheese curds) at the Tillamook cheese factory.

You could easily travel the Oregon coast in about 8 hours if you drove straight through, but you’d miss out on so much beauty and adventure along the way. Instead, plan to spend about 1 to 2 weeks to complete this itinerary, depending on how many coastal towns you want to stop in.

Oregon Outback Itinerary

The Oregon Outback itinerary will take you to a one-horse town in the high desert of Central Oregon. This is the best itinerary to choose if you love to hike, don’t mind a little dust in your boots, and want to avoid the crowds. This is the road less traveled.

Book your stay at one of two motels in Christmas Valley. About 4 hours and 30 minutes southeast of Portland, this small town is centrally located to several amazing and unique hikes in the area.

There are three major hikes worth checking out here. First, hike through a narrow, rocky canyon at Crack in the Ground. Then, be sure to bring a headlamp to explore the depths of Derrick Cave, an old lava tunnel.

And lastly, hike the perimeter of Fort Rock, an ancient volcano, as you watch for jack rabbits sprinting across the landscape. Then visit the outdoor museum, Fort Rock Homestead Village, for a taste of what life was once like in this Wild West.

Enjoy a hearty dinner one night at the Cowboy Dinner Tree. Just be sure to reserve your seat well in advance. They may have a rather remote location, but that doesn’t mean they aren’t booked solid!

Plan to spend about five days for this road trip. That gives two full days for travel and leaves three full days for hiking and exploring Oregon’s Outback.

At the end of this vacation, you’ll have experienced Oregon, untamed and untainted in its raw and natural beauty.

Portland, Oregon Itinerary

This itinerary is all about how to spend three perfect days in Portland, Oregon. And it’s the perfect itinerary for those who prefer the city or are only able to make a short visit to Oregon.

There’s a lot more to Portland than the rain. For starters, it has a great food and restaurant scene, with a strong affinity for coffee shops and microbreweries.

Portland is also known for its love of dogs and bikes, and for its many parks, gardens and bridges. But with so much to see and do, this guide will help you see the best highlights of the city.

Day One : Start the day with brunch at one of Portland’s many delicious brunching restaurants. A few excellent options include Broder Söder, Jam Cafe, or The Tin Shed ( a dog-friendly dining option! ).

Then, visit Powell’s books, the largest used book store in the world. Later, enjoy a cup of tea at the Lan Su Chinese Gardens . End the day with amazing views of Portland from the Portland Aerial Tram or Tom McCall Waterfront Park.

Day Two : On your second day, set out to explore the neighborhoods, admire the street art , and eat lunch at a food truck pod. Or get outdoors and go for an afternoon hike in Forest Park to discover the witch’s hut.

Day Three : On your final day in Portland, visit the International Rose Test Gardens and the Japanese Gardens at Washington Park. Then play around at Portland’s new and interactive art museum, Hopscotch. End your trip with drinks from one of Portland’s roof top bars.

If you have extra time, you can plan a day trip from Portland . Visit the Oregon Coast, head east to Mt. Hood, or travel south to Silver Falls State Park.

Oregon Trail Itinerary

Follow the path pioneers once took through Oregon on this Oregon Trail itinerary. Walk in the deep ruts of old covered wagons and imagine what it must have been like to traverse this country before the convenience of our smooth, paved freeways.

The Oregon Trail originated in Kansas and Missouri and spanned a total of seven states. However, this road trip focuses on the stretch of trail in Oregon.

Since I-84 roughly parallels the Oregon Trail through Oregon, there are two ways to approach this road trip. Option one is to drive east on I-84 from Portland to Baker City and back again. Or, option two is to fly into Boise, Idaho, rent a car, and drive west on I-84 to Portland.

The main highlight of this Oregon itinerary is the National Historic Oregon Trail Interpretive Center in Baker City, Oregon. At the interpretive center, discover an outdoor recreation of a covered wagon camp, watch live historical re-enactments, and hike alongside wagon ruts. This site covers 500 acres and includes over four miles of hiking.

Note: The Interpretive Center is currently closed for remodeling and has moved to a temporary location. For latest updates, visit their site here .

From Baker City, follow the trail west through the Grande Ronde Valley and over the Blue Mountains. Marvel at the Columbia River as you drive through the Gorge to The Dalles, where many pioneers rafted their wagons down the river.

TIP : Other locations to hike along actual Oregon Trail ruts are at Birch Creek near Huntington and Echo Meadows near Hermiston, Oregon.

While many pioneers settled in Oregon, others continued on to Washington. However this particular road trip ends in Portland, Oregon. Plan to spend about three to four days for this road trip.

Final Thoughts on Oregon Itineraries

From ocean to high desert, from the bustling city to dusty country roads, these five Oregon itineraries are sure to have a little something for everyone.

And whichever of these itineraries you choose, you’re sure to be stunned by Oregon’s beauty and diversity.

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Day 1 / Stop 1 – Stroll Through Washington Park

Day 1 / Stop 2 – Visit the Japanese Garden

Day 1 / Stop 3 – Enjoy the Company of Incredible Creatures at Oregon Zoo

Day 1 / Stop 4 – Explore Pittock Mansion

Day 1 / Stop 5 – Investigate Pioneer Courthouse Square

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3 Days in Portland OR: The Ultimate Weekend in Portland Itinerary

Day 3 in Portland Itinerary: The Northwest District

Where to Eat in Portland OR

Day 1 in Portland Itinerary: The Pearl District

Explore Powell’s City of Books, the world’s largest bookstore.

Grab a donut at Voodoo Donuts.

Walk across the Broadway Bridge and down the riverside.

Day 2 in Portland Itinerary: Forest Park & Portland’s Japanese Garden

… and then stop by the Rose Garden.

Visit Pittock Mansion, Portland’s most important historic building.

Explore the Witch’s Castle.

Spend the afternoon exploring Portland’s street food scene.

Visit the Freakybuttrue Peculiarium and Museum.

Wander down 23rd Avenue.

Enjoy an old movie at Cinema 21.

Where to Stay for a Long Weekend in Portland, Oregon

Check rates & book your stay at The Society Hotel!