NOMADasaurus Logo

The Perfect 3 Days in Portland Itinerary (2024 Update)

Lindsay Harvey

  • 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? 

3 Days In Portland Itinerary

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. 

Portland Saturday Market

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

Chinatown Portland

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.

Multnomah Falls Outside Of Portland

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.  

Portland Sign

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. 

Japanese Garden Portland

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.

DISCLAIMER: Some of the links in this article are affiliate links, which means if you book accommodation, tours or buy a product, we will receive a small commission at no extra cost to you. These commissions help us keep creating more free travel content to help people plan their holidays and adventures. We only recommend the best accommodations, tours and products that ourselves or our fantastic editorial team have personally experienced, and regularly review these. Thanks for your support, kind friend!

Lindsay Harvey

Lindsay Harvey

Hi, We’re Alesha and Jarryd!

Join the Team

We’ve been traveling the world together since 2008, searching for the planet’s best destinations and adventures.

Love Travel?

Sign up for our free weekly newsletter for the best travel tips, ideas and deals!

We respect your privacy. Unsubscribe at any time.

READ MORE...

The Ultimate 3 Days in New York City Itinerary (2024 Update)

25 Best Things To Do In Santa Fe, New Mexico (2024 Guide)

The 21 Best Things To Do In Richmond, Virginia (2024 Guide)

Related Posts

The perfect 3 days in atlanta itinerary (2024 guide), 30 best things to do in little rock, arkansas [2024 guide], 25 best things to do in texas (2024 guide), 19 of the best things to do in breckenridge, colorado (2024 guide), leave a comment cancel reply.

Save my name, email, and website in this browser for the next time I comment.

Nomadic Matt's Travel Site

Travel Better, Cheaper, Longer

14 Things to See and Do in Portland, Oregon

A colorful pink sunset over Portland, Oregon, USA, with Mount Hood in the background

Portland, Oregon, is one of America’s most unique cities. With a world-class food scene, plentiful local breweries, and postcard-perfect scenery, it’s surprising that more people don’t visit this eclectic city.

I first visited here in 2011 for Thanksgiving. While in Spain , I made friends who lived in Portland and paid them a visit on my way to Asia. What started as “like” during my first trip turned into love on my second.

I’ve visited the city nearly every year since. Portland is on the very tiny list of cities I would actually live in ( the nearby Oregon coast is stunning too! ).

What I really love about Portland is the high quality of life. It’s compact and easy to get around, there is good public transportation available, the locals are friendly, it’s environmentally conscious, and, most importantly, the food and beer scene here is amazing.

While the city developed a bit of a bad rap during the protests of 2020 and 2021, the overwhelming majority of that has been overblown by the media. While Portland isn’t perfect (no city ever is), it’s not nearly as “dangerous” as certain people would like you to believe. A city of over 600,000 people, it’s not being burnt to the ground and problems are confined to a small section downtown. Don’t let the media make you afraid to visit this incredible city.

To help you make the most of your visit, here are my favorite 14 things to see and do in Portland:

Table of Contents

1. Take a Walking Tour

2. see pittock mansion, 3. hike forest park, 4. browse at powell’s city of books, 5. devour delicious donuts, 6. wander the international rose test garden, 7. see the japanese garden, 8. visit the freakybutture peculiarium and museum, 9. take a food tour, 10. relax at laurelhurst park or washington park, 11. indulge at the food trucks, 12. visit the portland art museum, 13. drink some beer, 14. hike the columbia river gorge.

I always start my visits to a new city with a walking tour. It’s the best way to learn about a destination, get the lay of the land, see the main sights, and have an expert local guide answer all your questions.

Around Portland Tours offers almost a dozen different tours around town, focusing on food, the main sights, and Portland’s nearby hiking spots. Tours last 2-4 hours and start at around $29 USD. They’re a great way to kick off your visit. They also offer bike tours too for $59 USD!

You can also find niche tours if you want something different, like an underground tour or a ghost tour.

The stately Pittock Mansion in Portland, Oregon on a summer day

3229 NW Pittock Dr, +1 503-823-3623, pittockmansion.org. Open daily, from 10am–5pm (4pm in the winter, opens at noon on Tuesdays year-round). Admission is $16.50 USD.  

Located on the northwestern edge of town, Forest Park is one of the nation’s largest urban parks. Covering a sprawling 5,000 acres, it’s home to over 70 miles of hiking and biking trails. There are over 100 species of birds here, as well as 62 different species of mammals. It’s also home to the Witch’s Castle, an abandoned stone building covered in moss. (It has no connection to witches. The name came from students who used to use the site for secret parties in the 1980s).

Some trails worth checking out are the Wildwood Loop trail (easy, 2 hours), Forest Park Ridge Trail (moderate, 1.5 hours), and the Dogwood Wild Cherry Loop (easy, 1.5 hours).  

This is the largest independent and used bookstore in the world, home to over a million books. Established in 1971, the store takes up an entire city block and has 3,500 different sections. It buys upwards of 3,000 new and used books each and every day so if you’re a book lover like me, you could easily spend a good chunk of time here!

1005 W Burnside St, +1 800-878-7323, powells.com/locations/powells-city-of-books. Open daily 10am–9pm.  

Portland is known for its donuts. If you Google the city or search for it on social media, donuts will inevitably pop up (there even an donut walking tour here). Voodoo Doughnut put the city on the map with its weird and wonderful combinations, such as Cap’n Crunch or maple bacon. It also makes cream-filled phallic donuts as well — so you can see why it’s become a quirky staple of the city.

Some locals might argue that Voodoo is for tourists, preferring donuts from rival donut shop Blue Star instead. You can’t go wrong with either choice. They both have multiple locations around the city, so why not try both and see for yourself. You only live once, after all!  

Home to over 10,000 rose bushes and 610 varieties, this garden is where many companies test new varieties of roses (some are tested here years before they are commercially available). It’s the oldest rose test garden in the country. During World War I, roses from all around the world were sent here for testing and safekeeping. They also host an annual competition for the city’s best rose. The roses are in bloom between April and October, though there is also an amphitheater here that holds all kinds of events, such as classical music performances and plays. Don’t miss the Shakespeare Garden, which only has types of roses referenced in Shakespeare’s plays.

Guided walking tours of the city usually stop here since it’s one of the main highlights.

400 SW Kingston Ave, +1 503-823-3636. Open daily 5am–10pm. Admission is free.  

A beautiful waterfall in the Japanese Garden in Portland, Oregon

611 SW Kingston Ave, +1 503-223-1321, japanesegarden.org. Open daily 10am–5:30pm (closes at 3:30pm in the winter). Admission is $21.95 USD  

If you’re looking for something decidedly weird and unconventional during your trip, visit The Peculiarium. This creepy emporium is full of all kinds of weird drawings and souvenirs, gag toys, unknown oddities in jars, and even a giant Bigfoot statue. There are fake severed body parts (which are super lifelike), and they also serve fresh-baked cookies…with bugs, scorpions, and mealworms inside and on them.

The city’s slogan is “Keep Portland Weird.” This place reflects that perfectly.

2234 Northwest Thurman Street, +1 503-227-3164, peculiarium.com. Open Thursday-Tuesday, 11am–6pm. Admission is $10 USD ($7 USD on Tuesdays). Not suitable for kids.  

If you’re a foodie like me, you can’t visit Portland without taking a food tour. You’ll get to sample some of the city’s best food, learn about its culture and history, and meet other foodie travelers like yourself. It’s the best way to get the culinary lay of the land before you head off on your own to eat your way around town.

Forktown offers a few different food tours focused on different cuisines and regions of the city. It will give you a solid overview of what tasty offerings Stumptown can dish up. Tours last around three hours and cost 115 USD per person.

Lost Plate also runs a few specialized food tours, including one that focuses on donuts and one that sticks entirely to food trucks . Their tours start at $59 USD.  

Portland has tons of green space to relax in and enjoy. Laurelhurst Park was designed by the same team that designed Central Park in New York . It has a laid-back atmosphere and is popular with locals and visitors alike. There’s a duck pond, bike paths, and an off-leash dog area.

Washington Park is another great choice if you’re looking to lounge with a book and enjoy the weather. The park contains memorials for the Korean and Vietnam Wars, the Holocaust, and the Lewis and Clark expedition, and also offers beautiful vistas of Portland and Mt. Hood.  

People walking down a brick sidewalk lined with food trucks in Portland, Oregon

You can find plenty of tasty options on SW Fifth Ave and at the food pods (food truck lots) at Cartopia, Third Avenue, and Hawthorne Asylum. A couple of my favorites are Burger Stevens and Desi PDX. There are also tons of delicious foodie tours if you want to sample the best Portland has to offer.  

Opened in 1892, this is the oldest art museum in the Pacific Northwest. It’s also one of the oldest galleries in the country too (the seventh oldest to be exact). It’s home to over 42,000 items, from contemporary art to Native American works to Asian art and everything in between. There are permanent exhibitions, rotating temporary galleries, and an outdoor sculpture park. There’s a lot of variety here, so be sure to check the website to see what’s on during your visit.

1219 SW Park Ave, +1 503-226-2811, portlandartmuseum.org. Open Wednesday–Sunday 10am-5pm. Admission is $25 USD.  

Portland is one of the beer capitals of America. There are over 70 microbreweries in the city — more than any other city in the country — and Portlandians take their beer seriously. The craft beer movement started here back in the ’80s, well before it caught on elsewhere. Many breweries have their own tours, as well as their own restaurants, so you can enjoy a pint and a bite to eat.

There are also multi-brewery tours from companies like City Brew Tours (tours start at $89 USD). There’s also the Eastside Craft Brewery Walking Tour , which lasts 2.5 hours and costs $59 USD. If you’re a craft beer aficionado, be sure to indulge (responsibly)!  

A scenic vista overlooking the Columbia River Gorge near Portland, Oregon

Some suggested hikes are Dry Creek Falls (easy, 2 hours), Wahkeena Falls Loop (moderate, 3 hours), and Starvation Ridge and Warren Lake (hard, 8 hours). If you don’t have a car, there’s a daily shuttle, the Columbia Gorge Express, available. You can get a one-day Gorge Transit Pass for $15 USD, or an annual pass for $40 USD, if you’re planning on visiting the gorge a few times during your visit.

You can also take a guided tour of the gorge if you’d prefer something more organized.

Portland is one of my favorite American cities. It’s fun, eclectic, and energetic, and it has a lot to offer (especially if you’re a foodie or craft beer lover). It deserves far more attention than it gets — from domestic and international travelers alike. If you find yourself in the PNW, be sure to spend a few days here. Your tastebuds will thank you!

Book Your Trip to Portland: Logistical Tips and Tricks

Book Your Flight Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe so you always know no stone is left unturned.

Book Your Accommodation You can book your hostel with Hostelworld as they have the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels. Two suggested places to stay in Portland are:

  • HI Portland

Don’t Forget Travel Insurance Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

  • Safety Wing (best for everyone)
  • Insure My Trip (for those over 70)
  • Medjet (for additional evacuation coverage)

Looking for the Best Companies to Save Money With? Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road. They will save you money when you travel too.

Want More Information on the United States? Be sure to visit our robust destination guide on the United States for even more planning tips!

Got a comment on this article? Join the conversation on Facebook , Instagram , or Twitter and share your thoughts!

Disclosure: Please note that some of the links above may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I recommend only products and companies I use and the income goes to keeping the site community supported and ad free.

Related Posts

A car driving an open road in Death Valley, USA

Get my best stuff sent straight to you!

Pin it on pinterest.

View of Portland skyline with Mt Hood behind it during a pink sunrise, as seen from Pittock Mansion. Be sure to catch the sunshine at least once during your long weekend in Portland itinerary!

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

Some links in this post may be affiliate links. If you make a purchase through one of these links, we may earn a small commission at no extra cost to you. Please see our disclosure policy for more detail.

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!

Leave a Comment Cancel reply

We’re on the road right now – join in on the fun and follow @thebrokebackpacker on IG!

  • Meet the Team
  • Work with Us
  • Czech Republic
  • Netherlands
  • Switzerland
  • Scandinavia
  • Philippines
  • South Korea
  • New Zealand
  • South Africa
  • Budget Travel
  • Work & Travel
  • The Broke Backpacker Manifesto
  • Travel Resources
  • How to Travel on $10/day

Home » North America » Portland

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!

travel blog portland oregon

Unlock Our GREATEST Travel Secrets!

Sign up for our newsletter and get the best travel tips delivered right to your inbox.

Best Time To Visit Portland

Where to stay in portland, portland itinerary, day 1 itinerary in portland, day 2 itinerary in portland, portland itinerary: day 3 and beyond, staying safe in portland, day trips from portland, faq on portland itinerary.

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.

Where to Stay in Portland

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!

where to stay in Portland

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

 Portland itinerary

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!

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

Portland itinerary

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

Portland itinerary

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.

Portland Itinerary

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.

Washington Park | Japanese Garden | Oregon Zoo | Pittock Mansion | Pioneer Courthouse Square | Oregon Historical Society Museum

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.

travel blog portland oregon

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!

flickr-portland-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.

Oregon Zoo

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.

Pittock Mansion

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!

Pioneer Square at Christmas

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.

travel blog portland oregon

Wanna know how to pack like a pro? Well for a start you need the right gear….

These are packing cubes for the globetrotters and compression sacks for the  real adventurers – these babies are a traveller’s best kept secret. They organise yo’ packing and minimise volume too so you can pack MORE.

Or, y’know… you can stick to just chucking it all in your backpack…

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.

Forest Park

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!

travel blog portland oregon

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!

travel blog portland oregon

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.

travel blog portland oregon

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

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!

travel blog portland oregon

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!

International Rose Test 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.

travel blog portland oregon

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.

travel blog portland oregon

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.

travel blog portland 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!

Mount Hood Full Day Loop Tour From Portland

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.

Oregon Coast Day Tour Cannon Beach and Haystack Rock

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!

Eugene Highlights and Wine Tasting Combo

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!

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

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.

Active Roots Security Belt

Stash your cash safely with this money belt. It will keep your valuables safely concealed, no matter where you go.

It looks exactly like a normal belt  except for a SECRET interior pocket perfectly designed to hide a wad of cash, a passport photocopy or anything else you may wish to hide. Never get caught with your pants down again! (Unless you want to…)

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!

travel blog portland oregon

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

Aiden Freeborn

Portland Itinerary Pinterest Image

Share or save this post

travel blog portland oregon

Jetsetting Fools

Travel Far. Discover More. Spend Less.

Portland Itinerary A Perfect Weekend in Portland, Oregon by JetSettingFools.com

Portland Itinerary: Plan a Perfect Weekend in Portland, Oregon

Welcome to JetSetting Fools, here you will find our best travel tips for destinations worldwide. Some of the links on this site are Affiliate Links and if you use them to make a purchase, we may earn a commission. For more information, read our Disclosure Policy .

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!).

Subscribe Packing Checklist by JetSettingFools.com

More Things To Do in Portland, Oregon in 3 Days

Snow on Mt Hood, Portland, Oregon

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

Portland Rose Garden Roses

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 ?

Click here for a Free Vacation Budget Planner Banner by JetSettingFools.com

Pin it! See all of our travel pins on our JetSetting Fools Pinterest Board .

Portland Itinerary A Weekend in Portland, Oregon by JetSettingFools.com

Share This Story!

  • Click to share on Pinterest (Opens in new window)
  • Click to share on Facebook (Opens in new window)
  • Click to share on Twitter (Opens in new window)
  • Click to share on LinkedIn (Opens in new window)
  • Massachusetts
  • New Hampshire
  • North Carolina
  • Rhode Island
  • South Carolina
  • United Kingdom
  • Road Trip Itineraries
  • Travel Tips
  • Work With Me

Perfect Itinerary for One Day in Portland, Oregon

Standard Post

There is a lot to see in the areas surrounding Portland — the Oregon Coast, Willamette Valley, and Columbia River Gorge, just to name a few! And while the areas surrounding Portland are filled with tons of natural beauty, you will want to carve out at least one day in Portland, Oregon, to explore the city’s attractions. 

Downtown Portland is filled with tons to see, do, and, most importantly, eat! If you only have one day in Portland, Oregon, don’t worry — this is plenty of time to see the city’s highlights and premier attractions. Follow this one day in Portland, Oregon, itinerary for a taste of the donuts, coffee, bookstores, and natural beauty that await in Portland. 

Disclosure: Some of the links in this blog post are affiliate links, meaning that I earn a commission if you click through and make a purchase at no additional cost to you. This helps me keep the content on my website free for you to enjoy!

How to Spend One Day in Portland, Oregon  

Wondering how to spend one day in Portland, Oregon? I’ve got you covered! If you’re just passing through on a road trip of the Pacific Northwest and only have 24 hours in Portland, Oregon — this is the perfect one-day Portland itinerary for you! 

Coffee  

Portland takes its coffee production  pretty seriously, which is why you’ll have no trouble finding incredible craft coffee shops throughout Downtown Portland. Start your day with a cuppa jo from one of the following shops: 

  • Coava Coffee Roasters — Coava Coffee Roasters has a few locations in Downtown Portland. They roast all their single-origin coffee beans, and their handcrafted honey, vanilla, and mocha syrups are made fresh in-house. 
  • Good Coffee — Good Coffee serves exactly what they promise: good coffee! We loved visiting the location in the Woodlark Hotel and sitting in the gorgeous lobby (pictured below). I ordered one of their seasonal coffees (they rotate regularly), and it was delicious. 
  • Stumptown Coffee Roasters — Stumptown Coffee Roasters is a popular coffee chain that started in Portland. While they have locations in New York City, Los Angeles, and Kyoto, if you want to grab a coffee in the city where this brand got its roots, now is the perfect opportunity. 

A cup of coffee from a coffee shop  in Portland, Oregon sitting on a table

Donuts  

After grabbing your coffee, it’s time to try something else Portland is known for — donuts! Though Voodoo Doughnut is a popular stop in Portland (after all, it’s where this nationwide chain started!), the donut shop you must visit if you only have one day in Portland, Oregon, is Blue Star Donuts . 

Blue Star Donuts is known for inventing “donuts for grownups” with booze-infused donuts, like the Cointreau Crème Brûlée and Blueberry Bourbon Basil. However, there are plenty of other inventive flavors that all palates and ages can enjoy, like Tropical Delight, Matcha Lime Crumble, and Chocolate Bergamot Old Fashioned. 

Personally, I loved that Blue Star Donuts had different styles of donuts in addition to different flavors. You could get old-fashioned donuts, fritters, cake donuts, and fluffy yeast donuts all under the same roof. I also like that they use quality ingredients and collaborate with local businesses for the ingredients in their donuts. 

If you want to sample more donuts and coffee in Portland, check out this Portland Underground Donut Tour and Coffee and Donuts Morning Tour for the best of both worlds!

A donut on front of a blue wall at Blue Star Donuts in Portland, Oregon

Tom McCall Waterfront Park  

If you are visiting Portland on Saturday from March to December, head on over to the Portland Saturday Market at Tom McCall Waterfront Park. This market is known for being the country’s largest continually operating outdoor arts and crafts market and allows local vendors from the Pacific Northwest to put their goods on display. It is dog-friendly and filled with food vendors and live music performers. 

While you are at Tom McCall Waterfront Park, be sure to snag a picture of the Portland Oregon White Stag Sign . This landmark sign has been greeting visitors to the city of Portland since 1940, and it is illuminated at night. 

We also recommend walking down the street to the Lan Su Chinese Garden in Old Town Portland. This tranquil botanical garden features rare plants and stunning architecture that will leave you feeling like you have been whisked off to another country and culture — not in the middle of Downtown Portland! 

Powell’s City of Books  

After spending the morning at Tom McCall Waterfront Park, head over to Powell’s City of Books and meander around this legendary bookstore.

Powell’s City of Books is the world’s largest independent bookstore, with over four million books. They sell books of all kinds — from bestsellers and award winners to staff favorites and used books. The store is sorted by genre, so it’s easy to find what you are looking for — whether that be romance and mystery or children’s and nonfiction. 

After walking around Powell’s City of Books, spend some time exploring the surrounding Pearl District. The Pearl District is a trendy neighborhood in Portland filled with independent boutiques, cool bars, and charming art galleries. 

An aerial view of Powell's Books in Portland Oregon

Lunch  

Portland is well-known for its breweries (just as much as its coffee!), so be sure to grab lunch at one of the city’s breweries. These are a few of the most popular: 

  • Von Ebert Brewing & Kitchen — Von Ebert Brewing & Kitchen is an award-winning craft brewery in Portland. They have four locations, and one is right down the street from Powell’s Books, if you are walking. In addition to craft beer, they serve pizza, salads, sandwiches, and smoked meats for lunch and dinner. 
  • Little Beast Brewing Beer Garden — Little Beast Brewing is a craft brewery with one location in East Portland. They have a beautiful wrap-around patio and 16 beers on tap. They are located right next to Lawless BBQ, so you can get a Kansas City BBQ platter or sandwich to enjoy with your beer. 
  • Breakside Brewery — Breakside Brewery has five locations in Portland and the surrounding areas. They have a large tap list and serve tons of food for lunch, like burgers, sandwiches, salads, mac ‘n’ cheese, and appetizers. 

If you want to try more than one brewery in Portland, consider going on this brewery walking tour to check out some of the best breweries in East Portland. 

Washington Park  

After lunch, Lyft, Uber, or drive up to Washington Park . Washington Park is located two miles west of Downtown Portland on a hill overlooking the city and is filled with stunning gardens, historic homes, and notable landmarks. 

You could truly spend hours exploring all the attractions at Washington Park, but here are a few of the most notable to check out during your one day in Portland, Oregon: 

International Rose Test Garden  

The International Rose Test Garden is a free attraction in Washington Park that you can’t miss during one day in Portland, Oregon. In this garden, you will find more than 10,000 rose bushes representing 600+ rose varieties. 

The International Rose Test Garden started during World War I when hybridists sent flowers from around the world to Portland for testing, and some of the best roses are released into the market each year. The roses are usually in bloom from May to October, and the park is open from 5 AM – 10 PM. 

A women standing in a field of roses at the International Rose Test Garden in Portland

Hoyt Arboretum  

Hoyt Arboretum was founded in 1928 to conserve endangered species and educate the community. Now, it is an oasis in the city where visitors can go hiking on gorgeous trails, including the Fir Trail, Redwood Trail, and Maple Trail. You can see all the trails to choose from on this hiking trail map . 

Hoyt Arboretum is open from 5 AM – 10 PM daily, and there is no admission fee. There are restrooms in the Visitor’s Center. 

Portland Japanese Garden  

Portland Japanese Garden is a gorgeous and lush collection of gardens in Washington Park. You can visit the Natural Garden, Strolling Pond Garden, Tea Garden, Flat Garden, and Cultural Village. Spring, summer, and autumn are the most popular times to visit — but spring is preferable if you want to see the cherry blossoms. 

The garden is open from 10 AM – 6 PM on Wednesday through Monday, but they are closed on Tuesday. Admission is $21.95 per adult.  

Memorials & Statues  

There are several free memorials and statues you can visit in Washington Park, including the Oregon Holocaust Memorial, Vietnam Veterans of Oregon Memorial, and Sacagawea Memorial. We visited the Oregon Holocaust Memorial during our time at Washington Park and thought it was really sobering and well-put together.

The Holocaust Memorial in Washington Park in Portland.

More Attractions  

Other attractions to consider visiting at Washington Park include the Oregon Zoo, Archery Range, and the World Forestry Center’s Discovery Museum. 

Pittock Mansion  

Either before or after spending time at Washington Park, head just a bit further northwest to visit Pittock Mansion — a historic home that overlooks the Willamette River, Cascade Mountains, and Downtown Portland. 

Pittock Mansion was built in 1914. Tickets cost $14.50 per adult. Henry and Georgiana Pittock, who built the mansion, were one of the most influential families in Portland and built a financial empire by investing in the newspaper, real estate, banking, railroads, and other industries. 

Today, the Pittock Mansion is a house museum that tells the story of how Portland, Oregon, has evolved from a pioneer town at the end of the Oregon Trail to a modern, industrialized city through the lens of this historic family. 

Pittock Mansion is only open from 10 AM – 4 PM (and from 12 PM – 4 PM on Tuesdays), so be sure to plan your visit accordingly during your one day in Portland, Oregon, to give yourself enough time to explore this local history museum. 

Dinner & Drinks  

Finish your day in Portland, Oregon, with a nice dinner. There are tons of incredible places to eat in Portland, so believe me — it is difficult to choose just one! 

However, these are a few restaurants that I can recommend from my own experience, or were recommended to me by others: 

  • Noble Rot — My husband and I dined at Noble Rot for our anniversary, and we both agree it was one of our favorite meals ever . This restaurant grows all its own vegetables and herbs on the roof and has a wine-tasting menu, so you can get a flight with your meal. Our entrees were amazing. If you are looking for a “fancy” dinner, you will not regret dining at Noble Rot. 
  • Olympia Provisions — Olympia Provisions is in East Portland, like Noble Rot, and serves homemade charcuterie boards, small plates, and wine. If you are looking for a dinner that is on the lighter side, check this place out.  
  • Le Pigeon — Le Pigeon is one of the most famous restaurants in Portland. The restaurant serves a rotating menu of French-inspired fare with a six-course meal in a comfortable communal setting. If you want to dine at Le Pigeon, make reservations in advance and prepare to pay for a gourmet meal. 

Dinner at Noble Rot in Portland

Salt & Straw  

Before heading back to your hotel, head to Salt & Straw for a sweet treat to end the night. Salt & Straw is a popular ice cream chain that is spreading across the West Coast that started right here — in Portland! 

Salt & Straw is known for its inventive flavors, like Honey Lavender, Strawberry Honey Balsamic with Black Pepper, and Pear & Bleu Cheese. However, they also have classic flavors you will love, including Salted, Malted, Chocolate Chip Cookie Dough, and Double Fold Vanilla. Grab a scoop (or two!) to enjoy to end your one day in Portland. 

An ice cream cone in front of the Salt & Straw sign.

FAQs: One Day in Portland, Oregon  

Is one day enough for portland.

One day is enough to see the best of Downtown Portland. However, if you are planning to explore the areas surrounding Portland, such as the Willamette Valley, Oregon Coast, and Columbia River Gorge, it is best to spend three to four days in Portland (if not more) to experience all the best attractions in this gorgeous region. 

Is Portland a walkable city?

Overall, Downtown Portland is a walkable city. However, there are some places, like Washington Park, that you may need to Lyft or Uber to because of the steep climb. Personally, I recommend having a car in Portland, Oregon, so it is easier to go on day trips to nearby areas, like Cannon Beach and Multnomah Falls, during your trip.

What month is best to visit Portland?

The dry, sunny summer months of June, July, and August are the best time to visit Portland and the Pacific Northwest. However, the early fall months of September and October are also a beautiful time to visit Portland (and usually less busy).

Spend One Day in Portland, Oregon, During a Pacific Northwest Vacation  

If you are planning to spend one day in Portland, Oregon, during your road trip through the Pacific Northwest — you are in for an amazing treat! Portland is filled with excellent eateries, beautiful outdoor recreation spaces, and tons of craft coffee and beer. If you follow this one day in Portland, Oregon, itinerary — let me know what you think! 

travel blog portland oregon

Save This One Day in Portland, Oregon, Itinerary for Later

travel blog portland oregon

Looking for more things to do around Portland, Oregon? Check out these posts about the Pacific Northwest for more inspiration:

  • Perfect Cannon Beach Day Trip from Portland
  • Tillamook Cheese Factory Tour: Tips, Tricks & What You Need to Know
  • 10 Best Wineries to Visit in the Willamette Valley (+ Map & Helpful Tips)
  • Scenic Columbia River Gorge Day Trip from Portland

Copy of Standard Post

About the Author

Brittany Sawyer

Hi, I'm Brit! I'm a writer from Phoenix, AZ who loves coffee, golden retriever puppies, and obviously, travel! I help ordinary women (like me!) dream, plan, and do extraordinary travel experiences.

Session expired

Please log in again. The login page will open in a new tab. After logging in you can close it and return to this page.

Two Sisters Abroad

Two sisters exploring the world while trying to get college degrees

How to Spend One Perfect Day in Portland, Oregon

Pinterest Pin with a guide to how to spend 24 hours exploring Portland, Oregon.

Planning a quick trip to Portland and looking for the best things to do? Welcome to your complete one day in Portland itinerary and guide. Portland is a great city for outdoor lovers, beer lovers and anyone who enjoys great food. 

Ready to plan your trip? Keep reading for an itinerary for how to spend one wonderful day in Portland, Oregon.

Columbia River Gorge, Oregon.

When visiting Portland, I recommend staying in the Pearl District or Old Town area. These areas, I personally found, to feel safer than the main downtown area. There are also tons of walkable restaurants and shops nearby. 

The vast majority of hotels, however, are located in Portland Downtown. While this area is filled with nice hotels and upscale shops, it also has an extremely visible substance abuse problem. Personally, I didn’t feel very safe or comfortable walking around this part of Portland any time of day. Visible substance usage is common on almost every single street, at all times of day. 

If you do end up choosing a hotel in Portland Downtown (like we did), it’s easily walkable to the Pearl District/Old Town or a quick Uber/drive to other neighborhoods that have a lot to do and see.

Hotel Recommendations

  • Canopy by Hilton (Pearl District)
  • Hampton Inn And Suites (Pearl District)
  • Dossier (Downtown)
  • Moxy Portland (Downtown)

Portland is definitely a city for foodies, beer lovers and coffee lovers! You’ll find a huge selection of great restaurants with a variety of cuisines as well as fantastic breweries and coffee shops. 

Eating your way through the city, especially trying all of their famous donuts, is such a fun way to spend one day in Portland. 

Below are far too many recommendations for a single day in Portland, but I want you to have a variety of amazing spots to choose from! In the itinerary below, I will include my favorite restaurants from this list that I recommend for your one day in Portland. 

Coffee + Breakfast 

  • Deadstock Coffee (Old Town)
  • Case Study Coffee (Downtown, multiple locations)
  • Never Coffee (Downtown)
  • Java Man Coffee (Downtown, inside The Bidwell Marriott Portland)
  • Stumptown Coffee Roasters (Downtown)
  • Fried Egg I’m In Love (food truck Downtown, they also have two restaurants in other parts of the city) 

Lunch  

  • Pine Street Market (Downtown food hall, close by to the Portland Saturday Market) 
  • Deschutes Brewery Portland Public House (located in Old Town, great any  time of day!)
  • Brunch/Lunch

Dinner  

  • A casual ramen spot. 
  • Luc Lac Vietnamese (Downtown, casual and delicious) 

Drinks  

  • A great place for indoor/outdoor cocktails and casual eats 
  • A plant filled, beautiful bar and restaurant
  • Retro style bar and restaurant 
  • Vegan bar and restaurant 
  • Deschutes Brewery Portland Public House (located in the Pearl District)

Dessert/Treats – DONUTS

  • Coco Donuts (multiple locations) 
  • BlueStar (multiple locations) 
  • The Mini Donut Company (located in Pine Street Market) 
  • I’ll preface this by saying that I, personally, did not like Voodoo donuts. I thought they were dry and the frosting tasted like it was from a can. However, these donuts are so famous and so many people seem to love them, that perhaps I just got them on a bad day. 

One Day in Portland Itinerary

Start your day with brunch at the screen door.

The Screen Door , in the Pearl District, is the perfect place to grab a great meal to start a day of exploring! In addition to the menu and ambiance being great, the location in the heart of the Pearl District can’t be beat.

Visit the Incredible Powell’s City of Books

Powell’s City of Books , the largest independently owned bookstore in the country, is a must visit when in Portland! Located in the Pearl District, you could easily spend a couple hours here browsing the extensive new and used book sections. The bookstore is huge and there’s also a cafe where you can grab some drinks. 

Powell’s City of book is located about a 3 minute walk from The Screen Door restaurant. 

Powell's City of Books, Portland Oregon.

Explore Washington Park

Washington Park is without a doubt one of the coolest places to visit in Portland. This massive park houses an Arboretum, a Japanese Garden and the incredible International Rose Test Garden, just to name a few of its many attractions. 

Exploring Washington Park can easily be a full day activity, but if you only have a few hours to spare, definitely make sure you check out the Japanese Garden and the International Rose Test Garden. 

To get to Washington Park you can take public transportation, although this 20-30 minute trip will involve a 10-15 minute partially uphill walk. From Powell’s City of Books, the walk to the Japanese Garden will be about 35 minutes. You can also drive or Uber and this will take 5-7 minutes.

Wander Around the Japanese Garden

The Japanese Garden is a 5.5 acre garden space and truly an oasis. The Japanese architecture and wonderfully designed green spaces are beautiful to see. I would recommend spending at least 45 minutes here enjoying a peaceful walk. 

On site, there’s a tea house ( Umami Cafe ) for light bites. 

Admission to the garden is $21.95 for adults and slightly less for students, youth and seniors.

Japanese Garden in Washington Park, Portland, Oregon.

Be Amazed by the International Rose Test Garden

The International Rose Test Garden may have been my absolute favorite thing I saw in Portland. These gardens were established in 1917 and there are over 10,000 beautiful and unique roses growing throughout the gardens. There are 610 varieties of roses to see and there’s so many wonderful colors and arrangements. Even today, the garden still serves as a testing place for new varieties of roses. 

The best part, it’s completely free to visit! The rose gardens are open from May-October.

International Rose Test Garden, Portland, Oregon.

Go Back in Time at the Pittock Mansion

From Washington Park, take a quick 1.5 mile drive (or Uber) to the impressive Pittock Mansion . The Pittock family began constructing this beautiful French Renaissance-style home in 1912 and today it remains a beautiful house to tour. Although most of the original furnishings have been removed from the home, it’s been re-furnished in an historically accurate style with donated pieces. 

Tickets for a self-guided tour of the mansion are $15.50 and can be purchased online or on site. 

If you don’t want to pay to go into the mansion, but still want an amazing view of Portland, simply park in the parking lot and walk to the backyard. Here you’ll find one of the most beautiful viewpoints of downtown Portland! Additionally, there are free walking trails surrounding the mansion that you can check out.

Pittock Mansion in Portland, Oregon.

Enjoy Happy Hour at a Brewery

Portland is known for its craft beer, so a trip to PDX isn’t complete without visiting a brewery. One of my favorites is Deschutes Brewery in the Pearl District . This brewery has both indoor and outdoor seating as well as awesome food and drinks!

Go on a Ghost Tour (or another fun tour)

Portland, like most major cities, has a rough past and a spooky history. Personally, when I travel, I love going on ghost tours. It’s a fun way to see the city while also learning its history and hearing stories about its past. 

Usually these tours are an hour or two and you can go for a late dinner afterwards. 

BOOK A PORTLAND GHOST TOUR HERE!

If a ghost tour isn’t your vibe, there are other fun guided evening activities in Portland, like pub crawls or short sunset tourist flights with amazing views.

Nighttime tours in Portland:

  • Airplane Flight Tour over Portland, Oregon
  • Haunted Pub Tour
  • Weird Bar Crawl with Fanatical Local
  • Haunted Underground Shanghai Tunnel Tour with Brewery Tastings

Enjoy a Delicious Dinner and Drinks

Portland has some amazing restaurants and the perfect way to end your one day in Portland is with a delicious dinner. 

If you want to stay in the Downtown area, Luc Lac Vietnamese is a great option! This casual restaurant serves up delicious dishes. 

If you’d like to visit some fun bars after dinner, there are a few restaurant/neighborhood options. First, Kinboshi Ramen is a casual spot with amazing ramen. From here, there are some great bars within a couple minute’s walk. I recommend both Rontoms and Hey Love . 

North Alberta Street is also a fun area to have dinner and drinks. From Downtown, North Alberta Street is about 3.5 miles (or a 10 minute drive/Uber). Here you’ll find a variety of great bars and restaurants, but two great ones include Radio Room and The Bye Bye (vegan).

A Note on Safety

Portland, much like Seattle, has a very visible and sizable unhoused population. Much of this population also struggles with substance abuse. In Downtown Portland, including directly in front of many hotels, shops, restaurants and luxury stores, you will see constant drug usage. This was shocking to me when I first arrived in Portland.

While this doesn’t necessarily make Portland dangerous, I was definitely uncomfortable walking around Downtown alone, or even with my sister. The current situation would also make me seriously consider returning to Downtown Portland and I’d likely opt to stay in a different area.

Q&A – One Day in Portland, Oregon

  • One day in Portland is not enough to see all that the city has to offer, but it’s enough time to see some of the main highlights!
  • Yes! The downtown areas are very walkable. Additionally, the public transportation is quite good between neighborhoods. Washington Park – a huge green space and museum area – is also fantastic for walking and spending time outside.
  • Yes, Portland is a walkable city. There is also good public transportation and Ubers are readily available. Having a car is a great option, however, if you plan to get out of the city and explore the larger area.
  • June through September, so essentially summer and early fall, are the best time to visit Portland. You can take full advantage of the beautiful outdoor spaces, hikes and the International Rose Test Garden will be in full bloom.

In Conclusion

And just like that, you’ve spent one day in Portland! I hope you found this Portland guide to be helpful. If you have any questions, or any other activities to add to this itinerary, please let me know in the comments. 

If you have extra time in the Portland area, I definitely recommend a day trip out of the city to enjoy the beautiful natural areas nearby. There are a great selection of guided day tours to choose from and they’re definitely worth it.

Portland Scenic Tours

  • Half-Day Columbia River Gorge and Waterfall Hiking Tour
  • Mt Hood Day Trip from Portland to Multnomah Falls and Hood River
  • Full-Day Guided Oregon Coast Tour from Portland

Colombia River Gorge, Oregon.

From Portland, you can drive or take the train to Seattle in 3-3.5 hours. Visiting these cities in one trip is very common and doable!

Be sure to check out my Seattle guides before your trip!

  • Six Awesome Things to do if You Visit Seattle
  • How to Spend the Perfect 24 Hours in Seattle

Pinterest pin to a guide for how to spend one perfect day in Portland, Oregon.

This guide for how to spend one day in Portland includes affiliate links at no cost to you! Read our disclosure  here .

You may also like

Essential travel tips for visiting New Orleans, LA.

6 Essential New Orleans Travel Tips

Hotel Review of the Seven Hills Inn in the Berkshires, MA.

Review of The Seven Hills Inn – Berkshires, MA

Pinterest Pin with a winter guide to Newport, RI.

An Amazing Winter Weekend in Newport, Rhode Island

Leave a reply cancel reply.

Your email address will not be published. Required fields are marked *

  Notify me when new comments/replies are added to this post.

  • Work With Us
  • Blogging Bootcamp

Two Wandering Soles

  • Van Conversion Academy
  • Campervan Shop
  • Campervan Rentals
  • Plan a Trip
  • Itineraries
  • Destinations
  • Responsible Travel
  • Family Travel
  • Budget Travel
  • Scuba Diving
  • Travel Credit Cards
  • Digital Nomad
  • Teach English Abroad
  • Blogging Resources
  • Income Reports
  • Travel Shop
  • Meet Katie & Ben
  • About Two Wandering Soles
  • Personal Stuff
  • Portfolio & Press

Magical Oregon Road Trip: Steal this Itinerary!

Home » Blog » U.S.A. » Magical Oregon Road Trip: Steal this Itinerary!

With hundreds of miles of coastline, thick forests, snow capped mountains, remote hot springs, and raging waterfalls, there’s no arguing an Oregon is absolutely perfect for a road trip adventure.

Blue Pool Oregon Katie and Ben

From Crater Lake National Park to Mount Hood to adorable seaside towns, like Cannon Beach, there are so many places to visit on an Oregon road trip. 

Like, an overwhelming amount of places! 

But fear not, we’re here to help you plan the ultimate Oregon road trip .

Why trust our advice?

We live in Oregon and have spent months upon months taking road trips around our beautiful state. It’s easily one of our favorite things to do in Oregon .

And the best part is, we’re sharing all our favorite places, plus tons of insider tips and hidden gems, with you. (Aka all the stuff that has taken us several years of exploring to learn!)

Oregon Road Trip Contents

  • Oregon road trip itineraries

Tips for planning a road trip

Enroute entertainment, transportation.

  • Oregon road trip destinations

Grab a pen and paper (and maybe some coffee!) and let’s get started…

Psst! Keep these other articles on how to plan an epic USA road trip and money-saving tips for a cheap road trip handy while you plan!

Whether you are staying in a hotel, living in a campervan or RV, or you’re trekking in the backcountry, here is everything you’ll want to pack for the road . Plus tips and advice on making your next road trip go as smoothly as possible!

Road Trip packing list mobile banner

Oregon Road Trip Itineraries

We’ve created two perfect itineraries that you can steal for the ultimate Oregon road trip! 

On these routes you’ll find:

  • cute oceanside towns on the Oregon coast
  • the best things to do in Portland 
  • unforgettable hikes around the state
  • incredible foodie experiences
  • remote hot springs that are worth the effort to reach
  • the most beautiful waterfalls in the state
  • an Oregon road trip map of all the places we’d recommend

Plus, this route is flexible, so you can add or subtract places depending on how much time you have.

Whether you’re passing through on a West Coast road trip, or you’re lucky enough to call this state home (like we are!), we’ve put together a guide to planning the perfect road trip in Oregon.

Oregon Coast Road Trip

You could truly spend more than a month road tripping around Oregon and still not see everything. In fact, we still have plenty of places on our Oregon bucket list (like the Wallowas!) and we’ve been living and traveling in this region for years.

But don’t worry, we’ve narrowed it down for you into a manageable itinerary that will show you the best of Oregon.

We’ve created 1-week and 2-week itineraries that both start and end in Portland.  

You can certainly adjust the route if you don’t need it to loop back to Portland. We also have suggestions for more places if you have additional time.

One thing to note is that in the effort of seeing as many places in Oregon as possible, these itineraries are pretty action-packed. If one of the places looks especially cool to you, we’d recommend spending an additional day here or there so you don’t feel rushed. We’ve even made notes where we’d personally recommend you spend more time if possible.

1 Week Oregon Road Trip Itinerary

  • Day 1: Portland
  • Day 2: Astoria , Cannon Beach *
  • Day 3: Tillamook , Lincoln City
  • Day 4: Silver Falls , Willamette Valley
  • Day 5: Bend * 
  • Day 6: Smith Rock , Mount Hood , Hood River
  • Day 7: Columbia River Gorge , Portland

*places we’d recommend adding a day if you have time

2 Week Oregon Road Trip Itinerary

  • Day 2: Astoria
  • Day 3: Cannon Beach  
  • Day 4: Lincoln City  
  • Day 5: Florence
  • Day 6: Umpqua National Forest
  • Day 7: Crater Lake
  • Day 8: Bend
  • Day 9: Bend
  • Day 10: Smith Rock , Mount Hood
  • Day 11: Hood River
  • Day 12: Columbia River Gorge , Portland
  • Day 13: Day trip to Silver Falls and Willamette Valley , Portland
  • Day 14: Portland 

Have more time?

Here are more places we’d recommend adding to your Oregon road trip if you have the time!

Bandon : Cute oceanside town with some unique artsy attractions and a beautiful state park with gardens nearby.

Samuel H. Boardman : This is a State Scenic Corridor, and holy cow, we think it is one of the most underrated places in the state. That said, it is very far south and is kind of a pain to get to unless you don’t mind backtracking or looping down into California a bit.

Ashland : Home to just over 20,000 people, this small-ish town is undeniably charming. Surrounded by foothills and mountains, Ashland is known for its famed Shakespeare Festival, beautiful gardens, cute B&Bs and burgeoning restaurant scene.

Alvord Desert : This dry lake bed is an otherworldly landscape that is a unique camping spot. Chances are you’ve never seen anything quite like it!

Mount Hood Oregon road trip

We’ll be the first to admit, we’ve made plenty of road trip mistakes over the years. We’ve learned our lessons and we want to pass along our knowledge so your Oregon road trip can go as smoothly as possible!

1. Give yourself enough time

It can be tempting to pack as much as possible within your given time frame, but we’d strongly encourage you to plan your Oregon road trip with a bit of “buffer time”.

As you’re planning, take into account that things might go wrong. Bad traffic or a flat tire might delay you. Or maybe the weather turns when you have an epic hike planned, and you want to stay an extra day.

While planning your route from behind your computer screen, it may be tempting to think you can pack it all in and survive long stretches of driving on the road . Only to realize when you’re on the road, even a few hours can be exhausting and have you itching to get out of the car and stretch your legs!

2. Plan ahead during busy season

Sometimes the busy season is the only time you have to travel. We’ve certainly been there.

If you’re traveling to Oregon during the summer months, be sure to spend a little extra time planning:

  • Book your accommodation further in advance.
  • Research hidden spots and how to get away from the crowds.
  • Budget a little more money.
  • Plan to start your days earlier than you typically would.

3. Don’t stick to your route, exactly

After planning a road trip route, you might feel the need to follow it exactly. But we’d advise otherwise… 

Sometimes the best road trip stops are the unplanned adventures off the main road and into that cute little ocean-side town or a quick pull over on the side of the road that turns into a hike to an unknown viewpoint. 

Give yourself some “wiggle room” in your itinerary for the opportunity to get lost and explore some hidden gems along the way.

We have tons more tips, including common mistakes to avoid in our road trip planning guide . 

Road trip snacks

road trip hiking snacks

Maybe it’s because we always have food on the brain, but road trip snacks are an essential part of our road trip planning and experience. 

We try to have a mix of healthy and indulgent foods on hand in the car, because hunger can strike at any time during a long road trip.

Here are a few of our favorites:

  • Fresh fruit
  • Peanut butter-filled pretzels
  • Veggies and hummus
  • Dried fruit
  • Dark chocolate
Psst! Did you know a lot of our favorite hiking snacks double as great road trip snack options!?

Campervan+Budget+Road+Trip

If you’re like us, one of the first things we plan when going on a road trip is which audiobooks we want to listen to and which podcasts to download for our enroute entertainment. We put together some of our top recommendations in case you’re looking for something new to listen to.

  • Where the Crawdads Sing by Delia Owens: One of my favorite reads from 2020. A beautifully-descriptive coming of age tale about how society is quick to judge and misunderstand those deemed “outsiders”. It also reads like a love letter to nature.
  • A Walk in the Woods by Bill Bryson: This funny account of one man and his ill-prepared companion’s attempt to hike the Appalachian Trail. A humorous and adventurous quick read.
  • You are a Badass by Jen Sincero: If you need a little motivation right now (I’m with ya!), Jen will give you the kick in the pants you need to stop doubting yourself. It reads like you’re talking to a good friend.
  • Whatever You Do, Don’t Run: True Tales of a Botswana Safari Guide by Peter Allison: A collection of personal stories recounting hilarious and sometimes terrifying tales of life living in the African bush as a safari guide, coming face to face with some of the fiercest wild animals, and managing the hordes of camera-toting tourists. 
  • Shantaram by Gregory David Roberts: The thrilling story of an escaped convict who flees a maximum security prison in Australia, fleeing to Bombay with his guide and companion, where they can disappear forever in the criminal underworld.

If you like these recommendations and want more, we have an entire list of books for travelers – broken out by category, from memoirs to fictional travel stories. 

Podcasts 

  • Favorite Episodes: Mr. Hodges, All in the Family
  • Favorite Episodes: Lonely Planet, Patagonia, Burton, AWAY Luggage, Canva
  • Science Vs. (Gimlet Media): Dives into hot button topics and major political issues (from essential oils to immigration) and goes over the FACTS of both sides of the argument, while incorporating humor. 
  • Favorite Episodes: Brownie Lady, The Chase (interview with a “professional” streaker)

travel blog portland oregon

Most people will use their everyday car as the vehicle for their Oregon road trip. And that’s a great choice; however, there are other options to consider. Especially if you will be flying in from out of state. 

Campervan rental

It’s no secret we are big fans of #vanlife. If you want to give it a test drive, we’ve got tons of resources for you! 

Check out our list of top companies for USA Campervan Rentals , from budget to bougie, including exclusive discounts for our readers.

Related: If you already know you’re flying in and out of Portland, we also have a guide to the best campervan rentals in Portland specifically.

One company we’d recommend looking into is Escape Campervans . They have 12 different locations across North America (including Portland, making it a great choice for an Oregon road trip). They come fully loaded with all the gear you need for an epic road trip, and they are a good budget option.

BONUS: We’ve partnered with them to give you a 10% off discount when you use our link !

Rental cars

Renting a car is a great option for your road trip if you don’t want to put extra miles on your own vehicle, or are flying in from out of state. 

Personally, for road trips in the USA, we’ve had good experiences with RentalCars.com . We’ve booked through them several times and have found some really great deals. For example, we rented a small SUV for a road trip in Washington State and paid less than $30 per day, and in Tucson, Arizona we paid just $17 a day. Heck yes!

Prices vary depending on your location, number of days, season, and type of car. Our advice is to compare RentalCars.com to other platforms with your specifics so you can be sure you’re getting the best deal.

Oregon Road Trip Destinations

Here is where we’ll go over all of our recommended places to visit in Oregon to fit into either of the road trip itineraries we suggested above. 

Things+to+Do+in+Portland+Oregon+Portland+Skyline+View+and+Mount+Hood

Let’s start with the obvious. Portland. 

This will likely be the starting and ending point if you’re flying in from out of state. 

Dubbed the “weirdest city in the USA”, there’s plenty of things to keep you entertained in this metropolis. 

We’ve been to Portland at least a dozen times over the past few years (one of the perks of living in Oregon!) and each time we visit, we find new fun and quirky things to do.

In fact, we are constantly updating our things to do in Portland guide to include all our new finds so that you have TONS of ideas to choose from, but we’ll share some highlights with you below.

Things to do in Portland

  • Explore the cute and quirky Mississippi neighborhood
  • Get lost in at Powell’s City of Books , the largest independent bookstore in the world
  • Taste Portland’s best donuts (it’s probably not where you think)
  • Find zen at Portland’s Japanese Garden or the Lan Su Chinese Garden
  • Order a Spanish coffee at Huber’s Cafe
  • Hike to the Witch’s Castle

Have more time in Portland?

  • Head down to the Willamette Valley for wine tasting !
  • If Silver Falls State Park isn’t on your road trip route, consider making a day trip here from Portland. It can be combined with some time in the Willamette Valley for one epic day trip!
  • DISCOUNT: Book a tour with Lost Plate and get $5 off your tour with the code: twowanderingsoles

Where to stay in Portland

Things+to+Do+in+Portland+Restaurant+Por+Que+No+Taqueria

Below are our Portland Airbnb and hotel recommendations broken down by neighborhood.

Pearl District: This is where many of the touristy attractions are located, making it easy to walk around. That said, there are some dodgy areas and most hotels charge quite a bit for garage parking (which you’ll definitely want to have downtown). 

  • Hotel Lucia

Mississippi Neighborhood: This neighborhood has fun vibes and cool restaurants and shops. However, it is a bit far from some of the “must see” places, like Powell’s Bookstore.

  • Mississippi SkyNest
  • Pink House off Mississippi Ave

Central Eastside: Just beside the river, this is perhaps the best of both worlds . Near downtown, but more of a “neighborhood vibe”. 

  • Jupiter NEXT
  • Comfy Buckman Neighborhood Home

For more options, check out our guide to the best Airbnbs in Portland .

Astoria Oregon viewpoint

From Portland, you’ll make your way toward the Oregon Coast, beginning with the charming riverfront town of Astoria. 

With a cool vibe and a burgeoning food and craft beer scene, Astoria is a perfect place to start the coastal section of your Oregon road trip.

Situated at the mouth of the Columbia River Gorge, Astoria is steeped in history and has enough things to do to occupy a few days.

But if you’ve only got part of a day to explore, we’ve outlined some of our recommendations below.

Things to do in Astoria

  • Grab a latte at Coffee Girl , which is located at the end of a historic pier and has sweeping views of the Columbia River and the cargo ships that will likely be hanging out not far from shore.
  • Hike to the Cathedral Tree for a nice little jaunt in nature.
  • Walk along on the Astoria Riverwalk .
  • Grab a beer at Buoy Beer Co.

Have more time? We have a whole guide with things to do in Astoria , and we’d recommend adding a day if you can. 

Cannon Beach

Cannon Beach Oregon 2022

As you make your way down the coast, the next stop on your itinerary is Cannon Beach. With cedar shingled houses, a charming downtown strip, and a massive sandy beach with an iconic rock formation, it’s not hard to fall in love with Cannon Beach.

One of the most popular towns on the Oregon Coast , we find ourselves coming back time and time again. And once you see it, we think you’ll understand the allure.

Things to do in Cannon Beach

Things to Do in Cannon Beach Oregon

  • Marvel at the viewpoints in Ecola State Park
  • Have a bonfire on the beach with views of Haystack Rock
  • Eat fish and chips
  • See a waterfall next to the ocean at Hug Point

Want more tips? We have a whole article dedicated to the best things to do in Cannon Beach .

Where to stay in Cannon Beach:

  • Charming dog-friendly cottage
  • Splurge: The Ocean Lodge
  • Check out our round up of the best camping near Cannon Beach .

Tillamook 

Tillamook Creamery Oregon ice cream

As you pass through Tillamook on your way down the coast, be sure to stop at the famous Tillamook Creamery. 

Here, you can take a self-guided tour and see firsthand how the dairy is processed. 

And come hungry so you can indulge in a grilled cheese and ice cream from the source!

Lincoln City

Oregon+Coast+Road+Trip+_+Lincoln+City

As one of the largest and most commercialized cities on the Oregon Coast, Lincoln City is known for their bi-annual kite festivals, glass blowing community and eclectic, artsy vibe. 

While not as quaint as some of the smaller towns on the Oregon Coast, Lincoln City has a relatively large and spacious beach as well as a burgeoning foodie scene. We actually found ourselves enjoying the town more than we’d expected to.  

Things to do in Lincoln City

  • Scour the beach for intricately designed glass floats (balls). Through a program called Finders Keepers , local glass blowers “hide” the floats for people to find.
  • If you don’t find a glass float, craft your own at the Lincoln Glass Center .
  • Hike to God’s Thumb for beautiful meadows and dramatic coastal cliffs.
  • Get smoked salmon at Barnacle Bill’s Seafood Market .
  • Stroll through the (totally free!) Connie Hansen Garden Conservatory . Especially in spring, it’s filled with blooming flowers.

Where to stay in Lincoln City

  • The Starfish
  • Sandcastles and Sunsets
  • Camping: Devil’s Lake Campground

Silver Falls State Park

Silver Falls State Park Oregon

Next up is Silver Falls State Park, home to some of the most beautiful waterfalls in Oregon , as well as one of Oregon’s most popular hiking destinations. The park has a lot to offer everyone from experienced outdoor enthusiasts to families looking for a day hike. 

It’ll cost you $5 for a day-use parking pass at Silver Falls. If you plan on going to a lot of parks, it might also be worth it to get yourself the $30, 12-month parking pass for all Oregon State Parks .

For more information about your visit, including all of the best hikes in the park, check out our guide to Silver Falls State Park . 

Willamette National Forest

Sandwiched between Eugene and Bend, about an hour and a half drive from either direction, you can make it into the heart of the Willamette National Forest. There are so many things to do in this part of Oregon, we only scratched the surface. 

Cougar Hot Springs

Terwilliger (Cougar) Hot Spring Oregon

The setting of Cougar Hot Springs (also known as Terwilliger Hot Springs) is something that you would find at a luxurious spa, but it’s so much better because you are only surrounded by nature.

There are 5 rock-walled pools that could fit about 8 people comfortably. Be sure to arrive early as it gets busy later in the day. Entrance Fee is $6/day and the trail starts on the west side of the Cougar Reservoir. We have a complete guide to visiting Cougar Hot Spring on our sister site with directions on how to get there and information you’ll need to know before your visit.

Psst! Are you a big fan of hot springs? You’ll want to check out this detailed guide to the best hot springs in Oregon ! 

Tamolitch Blue Pool

Tamolitch Blue Pools Oregon

No filters were used in this photo – the water really is that blue!

And oh, so cold! Seriously, even on the hottest summer day, jumping in this spring-fed pond is sure to cover your body in goosebumps. But it is totally worth it, and feels amazing when you dry off in the sun. 

Tip: Be careful that you don’t jump in with anything in your pockets or sunglasses on your head. While we were there, a couple guys decked out in scuba gear were diving for all the valuable items people lose in the depths of the water (aka GoPros, watches, designer sunnies, wallet, etc.). Don’t be that guy (or gal!).

How to get there: Be sure to start from the proper Tamolitch Trailhead and hike the McKenzie River Trail north to the Blue Pool. We have all the directions and everything else you need to know in our guide to visiting the Tamolitch Blue Pool on our sister site. 

Sahalie and Koosah Falls

These two large waterfalls are only 10 minutes walk apart from each other and worth a quick stop. I know you can easily get sick of waterfalls in this region, you shouldn’t miss these. Park the lot next to Sahalie Falls and hike south to Koosah.

McCredie Hot Springs

McCreddie Hot Springs Oregon

If you’re a huge hot spring fanatic, you can add this one to your route too. It will be a bit out of the way, so plan accordingly. We’ve even got a guide to McCredie Hot Springs to help you plan your visit!

Where to stay near in the Willamette National Forest

  • Loloma Lodge
  • Belknap Hot Springs Lodge

Florence Oregon Coast

Situated at the mouth of the Siuslaw River, the charming seaside town of Florence boasts views of both the ocean and river coastlines. We also happen to think it has one of the cutest, most adorable town centers on the coast.  

Just beyond the city center, the sand dunes are Florence’s star attraction. If you prefer a slightly more relaxed pace of adventure, there are several great beaches, lakes, and lovely hiking trails nearby.

Things to do in Florence

  • Rent a sandboard and play on the dunes!
  • Visit Heceta Head Lighthouse , one of the most picturesque lighthouses on the coast
  • Wander the historic “old town” of Florence
  • Go to the Sea Lion Caves to see these gentle creatures in their natural habitat
  • Hike to Hobbit Beach , one of the most stunning stretches of sand on the coast
  • In the summer, check out the lively weekend farmer’s market

Where to stay in Florence

  • Heceta Beach Hideaway
  • Chicken coop glamping
  • Camping: Port of Siuslaw Campground

Umpqua National Forest

Umpqua Hot Springs Oregon

Home to some of the best hikes in Oregon , with lakes, waterfalls and mountains, Umpqua National Forest is well worth a visit. Located in Oregon’s southern Cascade Mountains, we fell in love with this area and wished we had longer to explore.

Toketee Falls

Toketee Falls Oregon

A short drive off of Highway 138, you can park your car and go for a short walk to the waterfall viewpoint. This massive two tier waterfall is a major symbol of the region. Be careful on the trail, the rocks can be slippery. 

Umpqua Hot Springs

Umpqua Hot Springs Oregon

There’s a good chance these hot springs have shown up in your Instagram before. There are a handful of pools big enough to fit 2 to 4 people. The hotter pools start at the top and they get cooler as the water flows down. As with all hot springs in the area, nudity is acceptable and to be expected. Just to give you fair warning so you don’t feel uncomfortable. 

We put together an entire guide to visiting Umpqua Hot Springs on our sister site, so you know exactly how to get there and what to expect when you do.

Watson Falls

Watson Falls Oregon

Not a far drive from Toketee Falls, Watson Falls is a nice 0.6 mile hike to a 272 foot waterfall. It’s an easy walk with not too many people when we visited. The first part you walk by a mossy babbling creek that leads up to the towering waterfall. You get a whole lotta nature within such a short hike.

Insider Tip:  There is a (free) dispersed campground with 5 spots called Lemolo Forebay 2. It is first come first serve and has a vault toilet. We’ve camped here twice and love this spot because it is tucked away from everything else and it is super peaceful. Oh, and did we mention it’s free?! Just be sure to clean up after yourself, please.

Diamond Lake

Stop off at Diamond Lake for a view of the lake and the surrounding mountains. If you have time, you can drive 12 miles all the way around the lake or take a paddle boat out from the resort. 

Where to stay in the Umpqua National Forest

  • Steamboat Inn
  • Wilderness Cabins, RV Park and Glamping: Umpqua’s Last Resort

Crater Lake National Park

Crater Lake Oregon

Between the deep blue color and the fact that this lake is inside a sleeping volcano, your jaw is sure to drop at the sight of Crater Lake. We think it’s one of the more underrated National Parks in the United States .

With a depth of 1,949 feet (594 m), Crater Lake is the deepest lake in the United States and the 3rd deepest in the world (for average depth; 9th in the world for maximum depth). Crater Lake has been entirely fed by rainwater and snowmelt, and it’s known for its unsurmountable clarity.

Visiting Crater Lake will surely be a highlight of your time in Oregon.

Things to do at Crater Lake

If possible, get here early as the summer crowds can make it difficult to find a parking spot. 

  • Viewpoints – The Rim Village Visitor Center has a nice overlook of the lake, but I wouldn’t say it was our favorite angle. Head to the east side of Crater Lake to Watchman’s Overlook to get a good view of Wizard Island up close. 
  • Want more hiking suggestions? Check out our guide to the best hikes in Crater Lake National Park for more options for all levels.
  • Swimming – Don’t forget your bathing suit because you can take a dip in the waters, but it’s only for the brave. Crater Lake water is only rain and snowmelt so it will be cold. You can hike down the Cleetwood Cove Trail to the boat launch and practice your cannonballs. 

Bend Oregon downtown

With close proximity to epic adventures as well as a fun and vibrant downtown, this mid-sized city in the heart of Central Oregon begs all types of travelers to fall in love.

Funny story… When we first wrote this article back in 2017, here’s what the “Bend section” said:

“If we were going to move to Oregon, we would without a doubt relocate to Bend. Like, we’ve already talked about it and looked up real estate… It is the perfect size town (in our opinion) — not too big, not too small.”

Fast forward a few years and we DID end up moving to this Central Oregon town in 2019.

There’s a perfect brewery-to-green-space ratio, cute shops, healthy restaurants, yoga studios and a river that cuts through town. With plenty of outdoor adventures just outside the city limits, there’s a lot to love about Bend.

Things to do in Bend, Oregon

Things to do in Bend Oregon Mount Bachelor

Being that this is our home base, we know Bend really well! Lucky for you, we put together a giant guide on all the fun things to do in Bend with recommendations on where to eat and stay, plus plenty of info about the town we now call home. 

Here are just a few of our suggestions…

  • Grab a pint: There are loads of microbreweries scattered through town just begging for a brewery crawl. In fact, you can follow the “ Bend Ale Trail ” and win a prize.
  • Picnic at Drake Park: This riverside park is a beautiful place to take a stroll in the morning or hang out with a picnic.
  • Cascade Lakes Highway: Drive along this highway (open seasonally) and stop by some gorgeous alpine lakes.
  • And while you’re at it, check out some more of our favorite restaurants in Bend .
  • Day Trip to Sisters: Sitting at the foothills of the Oregon Cascade Mountain Range, Sisters is the perfect launch pad for any adventure activities you want to do in the mountains.
  • Broken Top Hike is one of our favorite hikes in Central Oregon (though it is a longer one)
  • South Sister Summit : If you’re looking for a killer but super worthwhile hike, you can summit the third highest mountain in Oregon
  • Green Lakes Trail: Not too long or difficult, and beautiful lake views at the end
  • Visit Tumalo Falls: Just 12 miles west of the brewery-lined streets of downtown lies Tumalo Falls , a beautiful 97-foot waterfall in the Deschutes National Forest.

Where to stay in Bend

  • McMenamins Old St. Francis School
  • Splurge: Tethrow Hotel
  • Check out our round up of the best camping near Bend, Oregon .

Smith Rock State Park

Smith Rock Misery Ridge Hike Oregon

As you leave Bend and head north, you absolutely must make a stop at Smith Rock State Park. This is a rock climber’s heaven (in fact, this is where sport climbing began in the USA). But it’s also a great spot for both casual and avid hikers.

Smith Rock Hikes

If you’re short on time or don’t want too strenuous of a hike, follow the Crooked River Trail . If you want a more challenging trek, Misery Ridge is for you!

We have an entire guide to Smith Rock State Park with all of the information you need to plan your visit including more details on the best hikes in the park.

Lost Lake Viewpoint in Mount Hood National Forest, Oregon

Named one of the 7 wonders of Oregon   by the Oregon Tourism board, Mount Hood is certainly a sight to behold. 

Whether you’re passing through on your way to Hood River or you have a night or two to spend here, we recommend carving out some time to explore this area.

Things to do at Mount Hood National Forest

Lavender Field Mount Hood Oregon Katie

  • Get one of the best views of Mount Hood from Lost Lake , which is located deep in the Mt. Hood National Forest . Be sure to have a full tank of gas and preferably 4-wheel drive (we’ve done it before without 4WD, and it was a little rough!) You can spend the day there hiking around the lake or rent a kayak and paddle to the middle. There are plenty of cabins and campsites around too, but you’ll have to book at Lost Lake Resort well in advance. 
  • Go hiking! From epic trails where you can camp overnight, like Tom, Dick & Harry , to roadside trails that are well-worth the stop, like Tamanawas Falls , to the 42-mile loop that circumnavigates the mountain, known as the Timberline Trail, there are plenty of Mount Hood hikes for adventurers of all levels to choose from. 
  • Psst! Check out these other breathtaking Oregon lavender farms you can visit!
  • Go skiing (any time of the year!) . Mount Hood has the longest ski season in the United States, making it totally possible to get turns in January or on the Fourth of July!
  • Sample the local brews at Mt. Hood Brewing Co .

National Park Pass

Tip: The America the Beautiful Annual Park Pass covers entrance fees to over 2,000 Federal recreational sites (including Mt. Hood National Forest!) as well as all the US National Parks. You could save a lot of money on entrance fees if you are planning to visit multiple parks in the upcoming year.

Hood River Oregon water sports

This adorable town situated on the Columbia River is a perfect mix of laid back vibes with plenty of things to do.

In fact, we’re getting ready to publish a big ‘ol guide to the best things to do in Hood River, but if you want a taste of the highlights, see our list below.

Things to do in Hood River

  • Check out the water sports: The Columbia River is home to some of the best kitesurfing in the world, and Hood River is the prime place to be. If you’re keen to learn, Big Wind offers beginner classes. Or, simply watch the kite surfers from the comfort of shore.
  • Explore the Hood River Fruit Loop , a 35-mile scenic drive through delightful local farms, wineries, cideries, fruit stands, and orchards. We recommend visiting as many as possible, but not all are open year-round, so check out our guide to the best stops along the Hood River Fruit Loop  to create your self-guided tour. 
  • Recommended to us by a friend who’s a master brewer in Portland (coolest job ever?!), pFriem Family Brewers creates artisanal award-winning beers that will give you flavor explosion in your mouth.
  • Another large brewery in town is Full Sail Brewery . You can find their beers in pretty much any grocery store in the PNW. Try their IPA, it’s one of their flagship beers (see what I did there?!).
  • Our favorite brewery in town, Double Mountain , has great beers and excellent wood-fired pizzas.
  • Sip your way through the best wineries in Hood River . 
  • Get breakfast at Kickstand Coffee & Kitchen : This cute cafe is open all day, you could get lunch or dinner here too (they have great cocktails!), but we are obsessed with their breakfast offerings.
Psst! Check out our complete guide with all the fun things to do in Hood River to help you plan your trip!

Where to stay in Hood River

  • Inn at the Gorge
  • Splurge: Klickitat Treehouse

Columbia River Gorge

Things+to+do+in+Portland+Oregon+Multnomah+Falls

Less than 20 miles east of Portland, the Columbia River Gorge stretches over 80 miles through a canyon reaching up to 4,000 deep in places as it winds along the Columbia River, following the Oregon/Washington border. This stretch of canyon has been designated a National Scenic Area and is the largest in America.  

Known for its high concentration of waterfalls —the Gorge has over 90 on the Oregon side alone!—it’s one of the best places to see waterfalls near Portland . 

Note: To enter the Gorge, you’ll need to purchase a  Northwest Forest Pass  for $5 for a daily entry, or you can gain access to the national scenic area using your  America the Beautiful Annual Park Pass . 

Things to Do in the Columbia River Gorge

  • Road-trip along the 70-mile Historic Columbia River Highway , stopping to take in scenic viewpoints (including roadside waterfalls!) along the way.
  • Stop at the 100-year-old   Crown Point Vista House  observatory for ahhh-mazing views
  • Visit Multnomah Falls , the tallest waterfall in Oregon , where you can simply marvel and take photos or embark on a short hike.
  • Hike the Oneonta Trail and view the slot canyons from above.
  • Watch the seasonal salmon spawn , swimming from the ocean and heading upstream.
  • Take a river cruise and sample local craft beer and delicious pizza in Cascade Locks.

Bandon Oregon Coast

With just over 3,000 residents, this tiny oceanside town is a picturesque and laid-back place to stop during a road trip along Oregon’s coast. 

Wander past cute shops on the main street, enjoy amazing seafood and see a unique art exhibit that will both disgust and inspire you. 

Things to do in Bandon, Oregon

Bandon Oregon Washed Ashore

  • Face Rock State Scenic Viewpoint : Discover tide pools at low tide or watch the sunset behind these beautiful sea stack rock formations.
  • Washed Ashore: With the tagline “art to save the sea”, Washed Ashore builds and exhibits artwork made from trash that has washed up on the beach. Their intention is to educate the public about plastic pollution in our oceans and inspire people to make positive changes. How cool it that?!
  • Sample the local seafood at Tony’s Crab Shack or Bandon Fish Market . Both restaurants are highly rated and long-time favorites. 
  • Grab a local brew at Bandon Brewery . We enjoyed the beer, pizza and live music at this cozy joint.
  • Explore the gardens at Shore Acres State Park .

Samuel H. Boardman State Scenic Corridor

Samuel H. Boardman Scenic Corridor Oregon Coast

Just across the border from California, lies Samuel H. Boardman State Scenic Corridor, which is well worth a stop if you find yourself in the south of Oregon. 

With interesting sea stack rock formations and hiking trails, you can easily spend a day getting lost in the beauty before your eyes.

There are many turnouts, some with parking lots, that are worth stopping at. The Natural Bridges is a short hike with some pretty spectacular views. Secret Beach is a short hike down to the sandy beach when there is low tide. The trailhead for this is just north of Miller Creek on Highway 101. 

This city in southern Oregon is known for its Oregon Shakespeare Festival, which attracts nearly 400,000 people annually. If you will be taking your road trip between late April through December, we’d highly recommend passing through here to check out the festival. 

And if you’re not a huge fan of Shakespeare, don’t worry. The plays are not limited to just those of Shakespeare – in fact, there are many contemporary works as well as Shakespearean dramas, performed on 3 different stages throughout the 8-month event. 

Alvord Desert

Alvord Desert Oregon

Located in the southeastern part of the state, this is one of the most interesting and unexpected geographical landscapes in all of Oregon. (And that’s saying something!)

The massive dry lake bed known as the Alvord Desert will have you feeling like you’ve driven straight out of Oregon and landed on another planet entirely. Often referred to as “the playa”, the expanse of cracked earth extends for miles and is a popular destination for outdoor adventure-seekers. 

Things to do in Alvord

  • Go camping! It is BLM land, so you can technically park your van or pitch your tent anywhere on the playa. Just know you will need a self-contained vehicle, unless you want to stay near the Frog Spring access point, which has a drop toilet for public use. 
  • If you like hot springs, Willow Creek and Alvord Hot Springs are worth a visit.
  • Stop at Fields Station for a killer (and huge!) milkshake.

Go Wander Wild Banner

Are you planning a trip to Oregon?

Being that Oregon is our home state, we have TONS of content to help you plan your trip. Start with our Oregon Homepage and be sure to check out the articles below. Leave us a comment if you have any more questions!

  • Keep this list of epic things to do in Oregon handy.
  • Plan your  Oregon coast road trip  with our insider tips & map.
  • Don’t skip  Cannon Beach , our favorite small town in Oregon.
  • Check out all the  weirdly awesome things to do in Portland .
  • Read up on all the  fun things to do in Bend, Oregon .
  • There’s plenty of fun things to do in Hood River to plan a weekend trip!
  • You’ll want to keep this  road trip planning guide  handy.
  • And here’s some great  money-saving tips for a cheap road trip .
  • If you need more ideas, here are some incredible places to visit in Oregon .

Save this article on Pinterest for later!

Oregon Road Trip | Two Wandering SoOregon Road Trip | Two Wandering Soles

We want to hear from you!

Are you ready for your Oregon road trip? Where are you planning to go? Would you add anything to our list? Let us know in the comments below.

Comments (32) on “ Magical Oregon Road Trip: Steal this Itinerary! ”

Is the trail for Oneonta Gorge open? I’m interested in many of these places but have this one especially on my list (first time upcoming visitor to OR). I’ve read it was closed due to fire several years ago but this article appears to be more current than that? Is it open?

Hi Lori, you’re right, the 2017 fire really changed the Oneonta Gorge Trail. You can now hike above the gorge and see the waterfall at the end, but you’ll no longer be able to hike through the slot canyon.

What an amazing list! We are right there with you when it comes to moving to Bend, as we have recently done so ourselves! We absolutely fell in love with the city when we visited, and that’s when we knew it was time to take the leap and make it our new home.

We are from Vancouver Canada thinking of a early May trip to Oregon hoping to find some warmer and drier weather. Currently considering Hood River as aside from the above looking for a destination that facilitates e-biking preferring bike-ways vs shared roads and… has dog friendly restaurants, breweries etc. Yes the dog likes to come for the bike rides and is too large to be inconspicuous. Not looking for an itinerary but would be open to alternate destinations if you have any suggestions.

“Hey, I would love to put my comment on this blog post!

This blog post helps me a lot!

Thanks for sharing this content worldwide!”

Possibly coming to OR from Montana. We will be traveling in a 5th wheel and hoping to utilize Thousand Trail campgrounds. We plan to stay in OR for about 2 to 2 1/2 weeks. I’m lost on where to begin the trip. I love everything in your blog! We are new full timers! Help!!

what itinerary would you recommend from Las Vegas to Oregon leaving on a Monday returning Saturday?

Does the weather in the early weeks of October affect more than half of these destinations? Particularly, any hikes and Hot Springs?

Does anyone happen to have a road map of this great sounding adventure?!

Hey! Minnesota born & raised here! I’m happy I stumbled upon your blog! I’m wondering how long of a road trip you took to visit all 11 of these gorgeous places?

Hey Kati! We took about 11 days during our Oregon road trip. Of course, we’d recommend spending more time there, but we were pretty pressed for time that summer. Hope this helps!

Oregon is in my wish list due to beautiful canyons and volcanic fields. You have taken a beautiful road trip along the Oregon eastern side. I loved the pictures of Painted Hills.

Thank you so much Mihika! We hope you get to Oregon someday, and when you do let us know if you have any questions!

Hi Katie &Ben, great article on Hood River but you’ve mislabeled the image of the lavender farm in your article- the correct name of the lavender farm image you feature is Lavender Valley in Parkdale. Thank you for correcting the photo/ farm credit. ?

Hi Francisco! Thanks for the note, we have updated the photo and caption. We had a lovely time stopping by Lavender Valley, wish we could have stayed longer!

In my, just previous, comment I forgot to enter my email address: [email protected]

Looking to travel 2 days down the coast from Newport to Cresent City. Are there falls along the way worth viewing? We will be short hiking as well. Thanks for your assistance. Susan

Hi Susan! If you travel along the coast, we highly recommend stopping off along the Samuel J. Boardman State Scenic Corridor. There are some waterfalls and short hikes with amazing views!

Have you been to Polychrome Pool?

Hey Jessica, no we haven’t yet. Where is that located?!?

I just love this. Always searching for this kinds of idea. Really great thinking. Thanks for sharing.

You are very welcome, Suj!

Great list! We are with you about moving to Bend, as we just did! We loved it when we visited and decided to take the plunge and relocate.

Nice! That’s so great to hear! Can’t wait to visit Bend again someday!

this is one of the best list I have seen by far. You are doing an amazing. please make more and have fun. my trip will be so much better because of your work.

You are too kind Solomon! Thank you for you words of encouragement. We don’t plan to stop any time soon!

Amazing post.Love reading your post.Pictures are stunning.As a traveler i love road trips.I would love to visit this place with my girl friend.She loves these kinds of places.Thanks for the post.Keep sharing.

Thanks so much, Diego. Glad you really liked our article. We hope you and your girlfriend have the chance to visit Oregon sometime. Let us know if you have any questions about planning a trip to Oregon.

Wow very eye opening ! I never, ever, imagined Oregon like that… the pictures are beautiful and there’s a lot of things to do and see. Thanks for the article 🙂

Hey Steven, Thanks a lot, glad you liked it! Are you planning on going to Oregon soon?

Ahah I can only wish… I don’t have any vacation planned until the end of the year !

Maybe one to add to the list for someday 🙂

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

Save my name, email, and website in this browser for the next time I comment.

  • Work with Me
  • Start a Blog
  • Yearly Roundups
  • 101 in 1001 Goals
  • how to start a travel blog
  • tips for new bloggers
  • write me a guest post!
  • Work With Me

A Passion and A Passport

Proving Travel is Possible with a Full-Time 9-5

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.

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!

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.

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!

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.

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!

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.

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!

  • 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.

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!

  • 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…

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!

  • 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).

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!

  • 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!

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!

→ 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

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!

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 .

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!

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.

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!

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 .

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!

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.

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!

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.

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!

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!

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!

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!

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!

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!

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!

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!

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 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.

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!

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!

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!)

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.

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 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).

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!)

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.

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!)

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!

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!

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!  

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!

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)!

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!

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.  

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!

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?

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!

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.

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!

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.

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!

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!?

Leave a reply cancel reply.

Your email address will not be published. Required fields are marked *

Save my name, email, and website in this browser for the next time I comment.

You may also love...

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)!

Subscribe To The Newsletter

FOR TRAVEL INSPO   and   FUN

No spam, only fun!

Favorite Destinations

California.

  • About Jessica
  • How to Plan a Trip
  • Fave Travel Companies
  • Shop My Faves

Destinations

  • World Travel
  • San Francisco
  • Northern California
  • Southern California
  • Central Coast

Portland, OR   Travel Guide

Courtesy of Photo by Matt Payne of Durango, Colorado | Getty Images

travel blog portland oregon

23 Best Things To Do in Portland, OR

If you've seen the comedy "Portlandia," you know Portland, Oregon, as a bike-friendly city that's full of food carts, indie bookstores, farm-to-table restaurants and an embarrassing number of coffee shops. Most of these characterizations are

  • All Things To Do
  • 1-Day Itinerary
  • 2-Day Itinerary
  • 3-Day Itinerary

travel blog portland oregon

Washington Park Washington Park free

Many critics, travelers and locals agree that of all of Portland's parks (and they are numerous), Washington Park is perhaps the best. Washington Park is home to such notable landscaping feats as the Portland Japanese Garden and the International Rose Test Garden , as well as the World Forestry Center, Hoyt Arboretum and several memorials dedicated to pivotal points in Oregon's history.

There are also family-friendly attractions like the Oregon Zoo and the Portland Children's Museum, along with a large playground, soccer fields, tennis courts and an archery range. Just make sure you save plenty of time for a leisurely stroll down one of the many shady paths, which are often decorated with flower displays and fountains.

travel blog portland oregon

International Rose Test Garden International Rose Test Garden free

Not until you visit these sprawling gardens in Washington Park will you fully understand the reasoning behind one of Portland's nicknames, the City of Roses. Established in 1917 by Portlander Jesse A. Currey and city leaders, it began as a testing ground for roses from around the world. Today, it is still the oldest continuously operated public rose test garden in the United States.

Home to more than 10,000 rose bushes, the site also boasts a special Shakespeare Garden, which is festooned with roses named after the characters in William Shakespeare's plays. Recently, garden staff have also planted some of the fruit trees that populate the Bard's plays – fig, olive and medlar. Award-winning roses are found in the aptly named Gold Medal Garden. The Test Garden is full of current trial programs that might include miniature roses, David Austin roses (they receive no fungicides or insecticides), and new varieties sent by rose companies for evaluation. If you have your heart set on seeing the roses in full bloom, plan a visit in mid-June.

travel blog portland oregon

Portland Japanese Garden Portland Japanese Garden

U.S. News Insider Tip: Make a reservation a few days in advance for the Zen-like Umami Café, which offers Japanese teas and traditional confections like mochi and baked manju. You can't make reservations the day of, and there is often an hourlong or more wait. – Hannah Wallace

If you need an escape from urban landscapes, seek out Zen-like tranquility at the Japanese Garden within Washington Park . The 12-acre Portland Japanese Garden is made up of eight separate gardens that represent different styles of traditional Japanese gardening techniques. All of the gardens feature essential elements like stone, water and plants that come from influences of the Shinto, Buddhist and Taoist philosophies, creating a unique, serene environment where visitors feel they are becoming a part of nature. The garden also features the Kashintei Tea House, where visitors can see demonstrations of a traditional tea ceremony, and a Cultural Village where Ikebana, bonsai care and Japanese music classes take place. If you're visiting in late March or early April, don't miss the chance to see the cherry blossoms in full bloom. Because of the garden's higher elevation, its trees are on a different blooming schedule than the rest of the city. (Usually a bit later.)

travel blog portland oregon

Popular Tours

Half-Day Columbia River Gorge and Waterfall Hiking Tour

Half-Day Columbia River Gorge and Waterfall Hiking Tour

(1041 reviews)

from $ 66.00

Full-Day Guided Oregon Coast Tour from Portland

Full-Day Guided Oregon Coast Tour from Portland

(241 reviews)

from $ 129.00

2.5-hour Dinner Cruise on Willamette River

2. 5-hour Dinner Cruise on Willamette River

(278 reviews)

from $ 127.00

travel blog portland oregon

Powell's City of Books Powell's City of Books free

Whether or not you're an avid reader, Powell's City of Books is worth checking out. Four floors high, it occupies a square city block; in fact, this bookstore is so large that exploring it actually requires a map.

While you wander through the stacks, keep in mind that you are tracing the footsteps of great writers, many of whom – like Ursula K. Le Guin and Neil Gaiman – have scrawled their signatures on the building's pillars. You might also schedule your visit to coincide with a reading, as the book shop hosts events nearly every day totaling more than 500 author visits a year.

travel blog portland oregon

Lan Su Chinese Garden Lan Su Chinese Garden

Occupying an entire city block, the Lan Su Chinese Garden is among some of the only authentic Chinese gardens in the country. Modeled after China's Ming dynasty scholars gardens, the Lan Su Chinese Garden aims to be a place where people can escape the hustle of everyday life and connect with nature. In addition to featuring plants and trees native to China as well as an 8,000-square-foot lake, the garden also hosts a variety of Chinese cultural events and festivals, such as the Lunar New Year festival and lantern viewing evenings.

Many recent visitors said the gardens were a highlight of their trip to Portland, describing the space as "tranquil," "stunning" and an "urban oasis." They also highly recommended taking the guided tour, saying it added context to the beautiful and serene setting. Tours are included in the admission price and offered daily at noon and 1 p.m. Others recommended enjoying tea and snacks at the on-site teahouse. A few visitors warned that the area surrounding the garden is home to a large number of homeless people and suggested taking an Uber or Lyft to reach the garden to avoid having to walk within the neighborhood.

travel blog portland oregon

Portland's Forest Park Portland's Forest Park free

If you're looking to spend some time outside, but you aren't willing to make the trek to Mount Hood , Forest Park is the place to go. Spanning 5,200 acres, it's one of the largest urban parks in America.

Among the park's features is the 30-mile Wildwood Trail, which is part of the region's 40-mile loop system connecting pedestrian and trail routes along the Columbia River to Gresham through southeast Portland along the Willamette Greenway and back to the Marquam Trail in southwest Portland. To find a trailhead, check out Forest Park Conservancy's online maps or buy a water-resistant trail map at Powell's or a New Seasons Market. If you're an avid bird-watcher, keep your eyes peeled: it's not unusual to spot barred owls, Cooper's hawks or pileated woodpeckers in the tall trees.

travel blog portland oregon

Multnomah Falls Multnomah Falls free

If you're willing to venture about 30 miles east of downtown Portland, you'll have access to the tallest waterfall in Oregon  – Multnomah Falls. Located along the Historic Columbia River Highway, the falls are the most visited natural recreation site in the Pacific Northwest, according to the U.S. Forest Service. 

At 620 feet tall, the Multnomah Falls are not for the faint of heart. Visitors have the option of climbing a 1/4-mile trail to reach Benson Bridge, which gives them a closer look at the falls and is at the crux of the first tier. Another steep, 1.25-mile hike will take travelers to the top of the falls for incredible views of the Columbia River Gorge . The Multnomah Falls Lodge, located at the base of the falls, houses a gift shop, restrooms and a restaurant for patrons to enjoy before or after their hike.

travel blog portland oregon

Portland Saturday Market Portland Saturday Market free

Whether you're craving international foods or are in search of a unique souvenir, the Portland Saturday Market is the place to look. Running since 1974, the market is located on the northern side of Tom McCall Waterfront Park and features 150 booths filled with art, upcycled clothing, handmade toys, organic soaps, reclaimed wood cutting boards and jewelry – all made by local artisans .

After you've had your fill of shopping, satisfy your appetite at one of the many food booths, which serve everything from Nepalese and Uruguayan to North African and Polish cuisines. There's live music every Saturday at 11 a.m. and 2 p.m. (Check the market's Instagram to find out who will be performing.) 

travel blog portland oregon

Columbia River Gorge Waterfalls Tour from Portland, OR

(701 reviews)

from $ 89.00

Mt Hood Day Trip from Portland to Multnomah Falls and Hood River

Mt Hood Day Trip from Portland to Multnomah Falls and Hood River

(554 reviews)

from $ 130.00

Columbia Gorge Waterfalls and Mt. Hood Tour - Full Day

Columbia Gorge Waterfalls and Mt. Hood Tour - Full Day

(53 reviews)

travel blog portland oregon

Hoyt Arboretum Hoyt Arboretum free

Founded in 1928, the 189-acre Hoyt Arboretum features over 170 different tree families and 6,000 individual trees. The species represented originate from every continent except Antarctica. Visitors can either explore the arboretum on their own via the park's 12 miles of trails or take a guided tour. Travelers with children will want to check out the family-friendly activities like seed paper workshops and "Tree Time" for preschoolers. There are also adult classes on everything from forest bathing to mushroom identification walks (prices range from $15 to $30).

Past visitors raved about the arboretum and many expressed their surprise that such a tranquil place exists within city limits. Travelers also encouraged future tourists to take their time when exploring the trails and advised planning a trip around one of the arboretum's weekend guided walks.

travel blog portland oregon

Mount Hood Mount Hood

On clear days, you can see snowy Mount Hood, the highest mountain in Oregon (at 11,239 feet), from Portland. Mount Hood is the region's prime skiing area, with numerous powdery downhill and cross-country trails. Test your skills on the expert slopes at Mt. Hood Skibowl or hit Mt. Hood Meadows for some of the area's best terrain. Or, get cozy at Timberline Lodge, built thanks to Franklin D. Roosevelt's Works Progress Administration and Civilian Conservation Corps. The historic, stately lodge is also where Stanley Kubrick's "The Shining" was (partially) filmed. Spend the night here in one of 70 rustic rooms, or grab dinner at one of the lodge's seven eateries. 

Planning a summer getaway? Never fear: Mount Hood offers summer skiing as well, not to mention plenty of opportunities to hike and mountain bike. Mount Hood's main summer attraction is the Mt. Hood Adventure Park at Skibowl, which features hiking and biking trails, as well as numerous other warm-weather activities.

travel blog portland oregon

Portland Art Museum Portland Art Museum

As the oldest art museum in the Pacific Northwest, the Portland Art Museum set the bar high for its patrons. It is home to Oregon's most prestigious collection, including works from the European masters, Japanese screen prints and contemporary American pieces. There is also a sculpture garden and an area devoted to photography. But the museum's Native American gallery – which consists of more than 3,500 ancient and modern objects from more than 200 different tribes – is not to be missed.

Recent travelers admit that they got lost in the art at this Portland museum, which is easy to do since the large collection fills three connected buildings. Because the museum is somewhat of a maze to navigate, some travelers recommend figuring out which exhibits you're interested in ahead of time so you know exactly where to go in the museum before arriving (gallery maps can be found online). Others were particularly pleased with the temporary exhibitions, which have showcased the work of artists like Jeffrey Gibson and Oscar Howe, among others.

travel blog portland oregon

Oregon Museum of Science and Industry Oregon Museum of Science and Industry

Whether you need to keep the kids entertained for a few hours or just need a way to spend a rainy day, the Oregon Museum of Science and Industry is the place to go. This interactive museum (referred to by residents as OMSI) makes learning fun thanks to its five halls and five labs filled with hands-on exhibits devoted to physics, chemistry, paleontology and more. Other interactive offerings include a science playground specifically designed for young children.

And if you're a movie buff, you'll want to make your way to the museum's USS Blueback submarine, which was used to film "The Hunt for Red October," and is the most modern U.S. submarine on public display in the country. When you've exhausted the exhibits, take in a show at the Empirical Theater or marvel at the stars at the Kendall Planetarium. There's also a riverfront eatery on-site, Theory, that serves healthy sandwiches, bowls and salads. Adults will also enjoy OMSI's evening lectures called "Science Pubs" where you can grab a beer and learn about everything from beaver adaptation to weight stigma in healthcare.

travel blog portland oregon

Columbia River Gorge Columbia River Gorge free

U.S. News Insider Tip: After a morning hike in the gorge, stop for a late lunch and soft serve at Sugarpine Drive-In on your way back to Portland. Owned by former Portland/Brooklyn chefs Emily Cafazzo and Ryan Domingo, this Troutdale restuarant serves excellent, hearty sandwiches. – Hannah Wallace

The Columbia River flows 1,200 miles from British Columbia to the Pacific Ocean and forms a dramatic border between Washington and Oregon. Both sides offer spectacular views of the gorge – from some spots on the Washington side you can see clear views of Mount Hood . Multnomah Falls is probably the closest scenic attraction as you drive east from Portland. From there, stop in Hood River or White Salmon for lunch or dinner. Both cities have an array of eateries, breweries, ice cream shops and cafes. In White Salmon, make sure to visit the White Salmon Bakery , which makes delicious pastries and breakfast sandwiches (all on its freshly baked bread) and pop over to the owners' new wine shop, Soca , for a bottle of Oregon wine. In Hood River, head to one of a handful of breweries like pFriem Family Brewers, Ferment Brewing Co. or Double Mountain Brewery.

travel blog portland oregon

All-Inclusive Downtown Portland Food Tour

(39 reviews)

from $ 119.00

Haunted Underground Shanghai Tunnel Tour with Brewery Tastings

Haunted Underground Shanghai Tunnel Tour with Brewery Tastings

(170 reviews)

from $ 40.00

Willamette Valley Wine Tour with Lunch

Willamette Valley Wine Tour with Lunch

(384 reviews)

from $ 230.00

travel blog portland oregon

Portland Mercado Portland Mercado free

Both a community economic development project for Latino entrepreneurs and one of Portland's best food cart pods, Portland Mercado showcases cuisines from Columbia, Cuba, Peru, Oaxaca and the Yucatan.

Past visitors raved about the al pastor burrito at Fernando's Alegria and the chicken mole at the Oaxacan truck. Others were blown away by the patacones (twice-fried plantains) at Qué Bacano, the Columbian truck. Travelers love the vibe as well: colorful trucks, energetic live music and plentiful outdoor seating.

travel blog portland oregon

Pittock Mansion Pittock Mansion

The 16,000-square-foot Pittock Mansion is one of Portland's few historic attractions and definitely one of the most unique. Built between 1909 and 1914 by Henry Pittock – the owner of The Oregonian newspaper – and his wife Georgiana, it was designed after the French Renaissance style. This 44-room mansion (of which only 23 are open to the public) contains a Turkish smoking room, a library, a music room and two sleeping porches, among other features.

A monthly behind-the-scenes tour of the mansion ($22) allows you to see parts of the property not usually open to the public like Henry Pittock's private den and the third-floor servants' quarters. Check the mansion's website for details; tours are usually offered on Saturdays. Also, stop by the gift shop, which sells handcrafted items made by local vendors. You can also take a self-guided tour during visiting hours; maps are available at the front entrance and interpretive panels are stationed throughout the mansion.

travel blog portland oregon

Tom McCall Waterfront Park Tom McCall Waterfront Park free

Named for a former Oregonian governor, this 30-acre park stretches alongside the Willamette River in downtown Portland and provides some of the best views of the city's skyline. Because of its prime location, it hosts many of Portland's special events – including the ever-popular Oregon Brewers Festival and the Portland Rose Festival.

But even when the city isn't celebrating, there's plenty to do here. Locals congregate for afternoon strolls or picnics and families cool off on hot days at the Salmon Street Springs fountain. The park is also home to some historic monuments like the Founders Stone, the Japanese American Historical Plaza and the Police Memorial. The Portland Saturday Market is held within the park every weekend from March to Christmas Eve. If you're in need of a bite to eat, head to Pine Street Market – a food hall with that sits at the northern end of the park at Second Avenue and Pine Street.

travel blog portland oregon

Mount Tabor Park Mount Tabor Park free

Mount Tabor is a dormant volcanic cinder cone located 5 miles east of downtown Portland. It may sound like a trek, but the scenery is well worth it. At its summit, Mount Tabor provides vistas of both downtown and Mount Hood . Travelers can choose one of three trails that takes them to the top of Mount Tabor and around the park. Along the trails, you'll see three reservoirs, which used to be the source of the city's drinking water. If views and hiking don't interest you, maybe this will: Mount Tabor Park is home to the Portland Adult Soapbox Derby. Each year on the third Saturday in August, racers in wacky cars zoom down the park's hills for a chance to win the top spot.

Past travelers relished the long walks they took through Mount Tabor Park. The breathtaking views are repeatedly mentioned by visitors, the sportier of whom run up the 293 stairs. Know that you'll do a lot of uphill walking before you reach that reward, however.

travel blog portland oregon

The Central Eastside The Central Eastside free

U.S. News Insider Tip: Food lovers in Portland get their olive oil, grains and Rancho Gordo beans at Wellspent Market , a locally-owned provisions store that also sells a great selection of natural wines, ciders and beer. – Hannah Wallace

Once an industrial neighborhood, the Central Eastside has been percolating over the past six to eight years with breweries, restaurants and even a few stylish boutique hotels. Even if you don't stay at Kex , an Icelandic youth hostel, you should make a visit to its horseshoe-shaped bar, Pacific Standard , which is now manned by respected bartender and author, Jeffrey Morgenthaler. Time your visit for happy hour (3 to 6 p.m.) to enjoy a $2 discount on all menu items, including food.

travel blog portland oregon

2-hour Lunch Cruise on Willamette River

(156 reviews)

from $ 86.00

Morning Half-Day Multnomah Falls and Columbia River Gorge Waterfalls Tour from Portland

Morning Half-Day Multnomah Falls and Columbia River Gorge Waterfalls Tour from Portland

(652 reviews)

from $ 75.00

Waterfalls, Mt Hood, and Wine Tour (Tasting Fees Included)

Waterfalls, Mt Hood, and Wine Tour (Tasting Fees Included)

(10 reviews)

from $ 135.00

travel blog portland oregon

Pip's Original Doughnuts & Chai Pip's Original Doughnuts & Chai

Named after the orphan Pip in Charles Dickens' "Great Expectations," this eclectic little cafe on Fremont Street is where Portlanders go to get their doughnuts and house-made chai. Because these doughnuts are diminutive, you can order four, six, eight or even 12. Regular flavors like cinnamon sugar, raw honey and sea salt, Nutella and candied bacon maple are justly popular, but don't skip the seasonal flavors, which in summer months always include local berries and peaches.

A decade ago, owners Jamie and Nate Snell used their life savings to start their doughnut shop, and when banks would not give them a $10,000 loan they felt like orphans, and sought help from friends and family. (Hence the name, Pip's.) They've put a lot of love into it – Nate was the general contractor and Jamie did the design and painted the clouds that cover the walls. A fun Portland touch: On your birthday you can come in and get a dozen doughnuts for free.

travel blog portland oregon

Portland, Oregon, Brewery Tours Portland, Oregon, Brewery Tours

Portland is well-known for its craft beers. In fact, there are roughly 70 breweries in the city proper, meaning there are plenty of places to quench your thirst. Though you're welcome to stop by the breweries on your own, taking a guided brewery tour might be a better bet if you're only in Portland for a quick trip (and want someone else to worry about transportation). The tours generally stop at a few different breweries in the city, allowing participants to sample several different kinds of beer.

City Brew Tours , which travels by van, wins accolades from past tourgoers for its knowledgeable guides and wide range of beer samples. For the company's Original Brew Tour, which lasts approximately five hours, the $129 ticket price includes beer samples at four breweries and a meal at either Migration or Ex Novo, two local breweries. BrewCycle welcomes you to "cycle" on a trolley with other people as it winds its way from brewery to pub on the east or west side of Portland. (You can also rent out a whole trolley for a special occasion.) Tickets range from $20 to $25 per person, depending on the day, and do not include beer.

travel blog portland oregon

PSU Farmers Market PSU Farmers Market free

If you're in Portland on a Saturday, make a morning stop at the PSU Farmers Market. In addition to just-picked local produce, vendors peddle meat, beverages (including alcohol), dairy products, mushrooms, chocolate and more. Talented musicians typically busk for tips.

Past visitors said the market is worth walking through even if you don't plan on buying produce. Others were impressed with the smoked fish, excellent Jewish rye and beautiful flowers for sale. Travelers also raved about the prepared foods at the market, including tamales, breakfast burritos, cookies and more.

travel blog portland oregon

Oregon Zoo Oregon Zoo

Explore some of the world's cutest, ferocious and exotic critters at the Oregon Zoo. The zoo houses more than 2,500 animals representing more than 200 different species ranging from reptiles to big cats to insects. In 2021, the zoo opened new habitats for rhinos, primates and polar bears, which were the final improvements after a decade-long expansion project. Along with the animal exhibits, there are also behind-the-scenes tours, as well as a train and carousel.

Recent visitors reported loving the zoo for its manageable size and animal residents (especially the elephants). Reviewers say you should expect to spend about two to four hours exploring. A few travelers were frustrated to learn that advance ticket purchase is required, and a few griped about the cost of parking.

travel blog portland oregon

Freakybuttrue Peculiarium Freakybuttrue Peculiarium

You can tell when entering this art gallery/museum/gift shop that the owners, Mike Wellins and Lisa Freeman, love science fiction, horror, cryptozoology, unsolved urban legends and the mysterious. Wellins calls the Peculiarium an anti-museum: you won't find sterile rooms with squeaky floors or frowning guards. What you will find? Everything from an alien autopsy to a theremin, ghosts, D.B. Cooper and two (faux) vampire killing kits. At the adjacent snack bar, you can try Freeman's Frankenballs, Franken Fries and her famous Bug Sundaes (Tillamook ice cream with freeze-dried mealworms and cooked scorpions – stingers removed – on top). 

Visitors say that you definitely "Keep Portland Weird" in this quirky art museum/gift shop with pop horror displays and grotesqueries. Past visitors recommend checking out the gift shop first, and if you're amused, go ahead and pay admission to the museum. Otherwise, it may not be for you.

travel blog portland oregon

Full-Day Mt Hood Waterfall Tour with Lunch and Wine Tasting

(173 reviews)

from $ 179.00

Airplane Flight Tour over Portland, Oregon

Airplane Flight Tour over Portland, Oregon

from $ 99.00

Afternoon Half-Day Multnomah Falls and Columbia River Gorge Waterfalls Tour from Portland

Afternoon Half-Day Multnomah Falls and Columbia River Gorge Waterfalls Tour from Portland

(314 reviews)

Things to Do in Portland, OR FAQs

Explore more of portland, or, best hotels.

World Map

When To Visit

If you make a purchase from our site, we may earn a commission. This does not affect the quality or independence of our editorial content.

Recommended

The 50 Best Hotels in the USA 2024

Christina Maggitas February 6, 2024

travel blog portland oregon

The 32 Most Famous Landmarks in the World

Gwen Pratesi|Timothy J. Forster February 1, 2024

travel blog portland oregon

9 Top All-Inclusive Resorts in Florida for 2024

Gwen Pratesi|Amanda Norcross January 5, 2024

travel blog portland oregon

24 Top All-Inclusive Resorts in the U.S. for 2024

Erin Evans January 4, 2024

travel blog portland oregon

26 Top Adults-Only All-Inclusive Resorts for 2024

Zach Watson December 28, 2023

travel blog portland oregon

Solo Vacations: The 36 Best Places to Travel Alone in 2024

Lyn Mettler|Erin Vasta December 22, 2023

travel blog portland oregon

26 Cheap Beach Vacations for Travelers on a Budget

Kyle McCarthy|Sharael Kolberg December 4, 2023

travel blog portland oregon

The 50 Most Beautiful White Sand Beaches in the World

Holly Johnson December 1, 2023

travel blog portland oregon

The 26 Best Zoos in the U.S.

Rachael Hood November 16, 2023

travel blog portland oregon

44 Cheap Tropical Vacations That Feel Expensive

Holly Johnson|Alissa Grisler November 10, 2023

travel blog portland oregon

Ottsworld Unique Travel Experiences

How to Plan the Perfect Weekend in Portland

May 19, 2022   No Comments »

Home » Blog » Destinations » North America » America » Oregon » How to Plan the Perfect Weekend in Portland

February 27, 2018 No Comments »

In an effort to bring you some new voices on Ottsworld, here is a guest post from a fellow blogger and Portland Oregon resident Susan Stephens. She had laid out a perfect weekend itinerary for her hometown of Portland!  All opinions and experiences expressed here are hers. –Sherry

Portland, Oregon is a collection of diverse neighborhoods, each with its own ‘small town’ feel. These neighborhoods together weave a tapestry of everything that a big city offers. Portland has plenty of culture and entertainment, while also providing a sense of familiarity and friendliness found in smaller communities.

Most of us who live here are transplants. You have to look hard to find someone who was born and raised in Portland. We come from all over the globe. In this way, Portland is teeming with diversity; so many ideas and creativity in one place give the Rose City its life force, its subtle draw that makes you want to come back time and time again.

Table of Contents

How a Local Would Spend a Weekend in Portland Oregon

I often get asked for local Portland travel advice; if you had a ‘perfect weekend’ in your hometown, what would you do? Very often I find myself fantasizing about my ‘perfect weekend in Portland.’ If I had no obligations, nowhere to be and money was no object, what would that look like? Well, allow me to indulge…

Weekend in Portland Map

Here’s a custom map I made to make it easier for you to locate some of these special places for your weekend in Portland.

Perfect Weekend in Portland – Saturday

I start my perfect Portland weekend by going to school! Well, yes and no. The beautiful campus of Portland State University (my alma mater) hosts its popular farmers’ market every Saturday . Not only do they have dozens of vendors offering up fresh produce, locally made honey, bread, jams, and flowers, but there are also several made-to-order food vendors. This is where Pine State Biscuits got their start (more on them later). As Portland’s year-round flagship market since 1992, during the spring and summer months they also have chef demonstrations and live music.

Start in the Hawthorne Neighborhood

Time for breakfast! I head on over to the Hawthorne neighborhood , to the Fried Egg I’m In Love food cart . You can’t miss it – it’s bright yellow, I guess to represent an egg yolk? I usually opt for my favorite, the Yolko Ono breakfast sandwich. A fried egg, homemade pesto, and a hand-pressed sausage patty inside perfectly-grilled sourdough bread. The result? Breakfast heaven. Other notable favorites on the menu are the ‘Rito Suave burrito and Smells Like Protein Spirit sandwich. See a music theme going on here? See Other Portland Food Cart options here .

Across the street on Hawthorne Boulevard is Red Light Clothing Exchange . This funky space is a second-hand clothing mecca, with a huge variety of men’s and women’s duds in all sizes. I rarely walk out of there empty-handed. As you walk along the boulevard there are lots of shops and restaurants to explore.

Plan 2 days in Portland, Oregon – spend a weekend eating donuts and working them off!

Further down the street is McMenamins Bagdad theatre. It’s in a historic, Mediterranean-styled building reminiscent of Hollywood’s golden age. I’ll usually catch a show in the afternoon if I’m in the area, because why? You can order a slice of pizza and a beer to enjoy during the movie!

Just down the road from Hawthorne is Mt. Tabor Park. Set on a dormant volcano, it’s a great place to walk off that pizza and beer, and a great place to walk your dog! The park’s rise in elevation gives you a killer view of downtown Portland to the west.

weekend in portland Bagdad Theatre

Take a Dip at Kennedy School Hotel

The next stop is the Kennedy School Hotel. This is a (yep, you guessed it) historic converted schoolhouse that is a destination unto itself. They have several restaurants and pubs, a movie theatre, and a soaking pool on site. The pool is where I’m headed. If you are not a guest of the hotel, for a mere five bucks you can have a relaxing hot soak in their private outdoor courtyard.

Catch Some Live Music

It’s Saturday night, so I’m off to catch a show at Mississippi Studios , a music venue hosting both local and international acts on any given night. Located on Mississippi Ave, it’s an intimate space with a full bar serving burgers and sandwiches right next door. Portland has an abundance of home-grown musical talent, and this is a popular venue for artists to hone their chops.

weekend in portland

Read reviews for Portland hotels on Trip Advisor | Search and book a hotel in Portland

The Perfect Weekend in Portland – Sunday

Earlier I mentioned Pine State Biscuits . These guys quickly graduated from a food cart to a brick-and-mortar with four locations! Their signature item, the Reggie Deluxe, is a flaky homemade biscuit holding a perfectly-cooked fried chicken breast underneath bacon, cheese, and a fried egg. Get there early or suffer the line!

Take an Urban Hike

If it’s a nice day (i.e. not raining), I’ll head downtown and take a walk or bike ride on the East side esplanade along the majestic Willamette River. A three-mile loop will take you across two of Portland’s many bridges to the picturesque Tom McCall Waterfront Park and back. If I’m not feeling a stunning riverwalk along the Portland city skyline, I’ll go to Forest Park (one of the largest urban parks in the U.S.) and hike up to the Witches Castle. It’s presumably haunted!

For more ideas on things to do in Portland, check out these Get Your Guide popular Portland tours:

Get Serious About Your Portland Coffee

What’s a weekend in Portland without coffee? After a scenic workout, I like to drag my coffee-craving, brunch-loving, hipster-embracing self to a nearby coffee shop. I frequent Grendel’s or Coava Coffee Roasters . Portlanders are as serious about their coffee as wine connoisseurs are about their wine. There are so many great coffee houses to choose from all over town.

weekend in portland

Shopping and Portland’s Street Art Scene

I’m not much of a shopper, but I do love to browse unusual stores, and Cargo fits the bill. They directly import their goods from around the world, including gifts, home decor, furniture, and textiles. The perfect place to shop for that hard-to-shop-for person.

One of the great things about Portland is the street art! As you meander around town, you cannot help but run into several fantastic murals and sculptures. There are hundreds all over town. There is even a map you can download that will show you a map of all of the current street art , much of which is commissioned by the city.

Try the Best BBQ in Portland

Another food cart-turned-restaurant is People’s Pig . The BEST BBQ in all of Portland. Vegetarians beware! Order your pig tucked in a sandwich or by itself, with a side of collard greens and house-made macaroni salad. And don’t forget the side of cornbread drizzled with honey. YUM.

weekend in portland street art

We All Scream for Portland Ice Cream

I’m rounding out my perfect Portland weekend with ice cream! For this, I go back to Mississippi Avenue, to Ruby Jewel Scoops . They offer a rotating array of unique flavors, along with the usual suspects. It was hard to choose between the Honey Lavender and the Creme de la Earl Grey + Chocolate. Mississippi Ave has a plethora of unique, locally-owned shops, restaurants, and bars.

If you find yourself looking for things to do for a weekend in Portland, I hope you’ll go local and try out some of the shopping, food, outdoor space, and art. The places I’ve mentioned are just the highlights. I’ve been here 20 years and I still haven’t seen it all!

Like the finest treasure, Portland is equal parts magnificent and melancholy, wild and tame, uncomfortable and cozy. Bottom line is, Portland is everything. At least to me! I hope you’ll come to visit and see for yourself all that Portland, Oregon has to offer.

Places to stay in Portland

Other pacific northwest articles you may enjoy.

Savor Seattle at Pike’s Place

Unique places to visit in Northern California

Meet the Author

Susan Stephens is a scientist-turned-travel-writer and a transplant from the Midwest. She has lived in Portland, Oregon for over twenty years. Her travel blog is dedicated to helping people discover the beauty of the Pacific Northwest. Please visit her website – Explorer Sue – to start planning your next Pacific Northwest adventure!

You can follow her on:  Instagram @pdxtravelgal  |  Facebook ExplorerSue   |  Twitter @PDXTravelGal  |  Pinterest ExplorerSue

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

* Your Name

* Your Email

Save my name, email, and website in this browser for the next time I comment.

Notify me of follow-up comments by email.

Notify me of new posts by email.

Who is Sherry Ott?

sherry-avatar

I'm Sherry, a corporate cube dweller turned nomadic traveler. I travel to off-the-beaten-path destinations to bring you unique travel experiences and photography. But it's not just about travel, it's also about life experiences of a middle age wanderer.

Learn More New? Start Here!

Follow my Travels.

travel blog portland oregon

Get my best travel tips,

Unique destination ideas,, and travel discounts, in my weekly email.

Never see this message again.

PORTLAND’S ONLY UNDERGROUND DOUGHNUT TOUR

Insider’s tip: decadent dining in downtown portland.

  • Restaurants

A DAY OF WINE, WATERFALLS, AND WONDERFUL VIEWS

Insider’s tip: satisfy your sweet tooth at the salt and straw, a morning tour of the greater portland area.

  • Sightseeing

INSIDER’S TIP: THE UNIQUE BEAUTY OF PORTLAND’S ART SCENE

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.

The interior lounge and bar area at The Hoxton, a hotel in Portland, Oregon

PORTLAND, OREGON

A living room, fireplace, and city view in a suite at The Nines, a hotel in Portland, Oregon

STAY INSPIRED

A spread of beer, burgers, fries, salads, and more at a restaurant in Portland, Oregon

These Are The Best Breweries In Portland, Oregon

itinerary-portland-816x612.jpg

Delicious Food, Designer Hotels, and More Are Waiting for You in Portland, Oregon

An ornate interior in Portland, Oregon

Hotels to Book for a Trip to Portland

OFFER DETAILS Prices will vary depending on occupancy, availability, length of stay, and itinerary options selected. Itineraries are only available through the reservations line at 1-833-794-1694. Travel + Leisure GO pricing is only available to active Travel + Leisure GO accounts. Rates are subject to limited availability and may be discontinued without notice. Cannot be combined with any other offer. All monetary amounts are noted in U.S. Dollars unless otherwise noted. Itinerary pricing does not include additional expenses such as airfare, transportation, resort fees, taxes, local fees and other incidental expenses. Blackout dates may apply. Hotel prices displayed are per room, per stay based on the cheapest double room available, inclusive of all taxes and service fees — but exclude any fees payable at or to the hotel. Separate terms & conditions may apply for hotels and activities. Please check individual hotel or airline for details. Valid for new bookings only. Your credit card will be charged the total cost of your reservation at time of booking. No reservation is guaranteed until full payment is received. Void where prohibited by law.

COVID-19 TRAVEL ALERT Please remember to check government advisories before booking and traveling.

CALIFORNIA SELLER OF TRAVEL REG. NO. 21414-50 Registration as a Seller of Travel does not constitute approval by the State of California. Fla. Seller of Travel Reg. No. ST-35519. Washington Seller of Travel. Reg. No. 603-338-177.

HI TAT Broker ID TA-075-433-7792-01

The World Was Here First

The Perfect 5 to 7 Day Pacific Northwest Itinerary

Last Updated on January 11, 2024

by Audrey Webster

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.

travel blog portland oregon

The Pacific Northwest should be on your radar for a number of reasons. Within the region, you have access to mountains, forests, and coastline along with unique and vibrant cities. The PNW generally includes Washington State, Oregon, Idaho, and British Columbia. However, for your 5 to 7-day Pacific Northwest itinerary, we’re going to look specifically at Washington and Oregon.

Should you have more time to spend in the area, extend your trip to visit Idaho and BC. We’ll include a combination of urban and natural areas, as well as destinations that are a bit more off the beaten path.

Table of Contents

Best Time to Visit the Pacific Northwest

The best time to visit the PNW is in the summer. Summers tend to be mild–they are warm and comfortable. During this time of year, you can plan to pack sandals, shorts, and a light jacket. Always have a rain jacket on hand as the PNW is known for brief and sudden downpours before returning to beautiful blue skies.

Keep in mind that a visit in August or September might force you to travel around wildfires. Eastern and central Washington and Oregon experience their highest number of wildfires during these months, so it might be the case that some trails or forest areas are off-limits to visitors. 

Summer may be the best time to visit, but you can still visit during other months. Visiting national parks or state forests during the fall provides the opportunity to witness the stunning changing of the leaves.

In October, it’s usually still warm enough to camp and you can enjoy the orange and yellow leaves. The winter months in Washington and Oregon are cold and wet, but if you enjoy winter sports, consider paying a visit to the PNW during this time.

There are several ski resorts as well as opportunities for backcountry skiing and snowshoeing. 

As a general rule of thumb, never visit the PNW without a rain jacket or umbrella. The area is known for being flush with green all year round, but this is only possible due to large amounts of rain. Make sure you pack carefully for whichever season you plan to visit. 

The Oregon Coast is a highlight of the Pacific Northwest

5 to 7-Day Pacific Northwest Itinerary

If you’re lucky enough to have a full 7 days to spend in the PNW, take this itinerary to guide your travels. We also have options for a 5-day itinerary that will take you to some of the PNW’s best places.

If you need to rent a car for this trip, then you can browse Rentalcars.com which aggregates prices across a number of companies. Alternatively, you can also consider renting an RV or a campervan from Outdoorsy.

Day 1 – Seattle, Washington

Beginning your travels in Seattle, Washington is the perfect way to kick off your itinerary. You can visit the city in one day, but it’s ideal if you can spare more than that.

Seattle is most well known for the Space Needle, museums, and Pike’s Place Market, where you’ll find delicious seafood, outstanding views of Puget Sound, and the original Starbucks coffee.

The Chihuly is a blown glass museum that tends to be a fan favorite. You must also make sure to pay the famous gum wall at Pike’s Place a visit. 

Spending a day in Seattle can give you a great taste for the city before continuing onto the rest of your PNW itinerary.

Where to Stay in Seattle

The Mediterranean Inn – Situated within walking distance of the iconic Space Needle, this hotel is a great option for staying in Seattle. You can choose from a range of rooms including some with self-catering facilities and there is a 24-hour reception.

Inn at the Market  – Located close to the iconic Pike Place Market, this boutique hotel is a great option if you’re not worried about your budget. There are a range of comfortable rooms to choose from and a great rooftop bar with spectacular views of Seattle.

HotelHotel Hostel — If you’re travelling on a budget or are solo and looking for a social atmosphere, then this hostel is a great choice! Centrally located in Seattle, they offer both private rooms and dorms with good common areas as well!

Private Rental — If you’d prefer to have your own place to stay in Seattle, then it’s worth considering a private apartment for your stay. There are a number of great properties to choose from, from a basic one-bedroom apartment to unique stays like this urban treehouse .

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

Seattle's Iconic Skyline

Day 2 – Olympic National Park & Rialto Beach

For day two, head northwest toward Olympic National Park . If you sat on the waterfront in Seattle and looked west, you most likely saw a mountain range–this is Hurricane Ridge on the Olympic peninsula. Here you’ll find forests, mountains, and beaches to explore.

At the furthest tip of the peninsula is the stunning Cape Flattery. There’s a road that goes around the outskirts of the park, but you should make sure to venture into the mountains and rainforests, namely the Hoh Rainforest. 

One of the most popular areas of the Olympics is Rialto Beach. It’s near La Push, made famous because of the Twilight movies filmed there. Rialto is unique for its stacks of driftwood and ecosystems, a combination of beach and coastal forest.

If your itinerary allows, try to visit during sunset. On a clear summer evening, set up a blanket and watch the gorgeous sunset over the ocean. Those who aren’t interested in Olympic NP, consider staying inland and spending this day in Mount Rainier National Park , instead.

Hall of Mosses in Olympic National Park

Where to Stay Near Olympic National Park

Olympic Lodge – Located in Port Angeles, this is one of the top options if you’d prefer a luxury accommodation to come back to after exploring the National Park. They have a number of great rooms and great facilities such as a swimming pool and a restaurant on site.

Emerald Valley Inn – Also situated in Port Angeles, this inn is located near the park entrance making it convenient for those who want to start exploring early! They have a range of rooms available including some with a patio and there is also a restaurant on site.

Greenhouse Inn by the Bay – Located in the town of Sequim, this bed and breakfast is the perfect cosy place to rest your head after a day of exploring the park. They have a range of comfortable rooms to choose from, with breakfast included in the nightly rate and a nice garden to relax in.

Private Rental – Another great accommodation option near Olympic National Park is a private rental. There are several options near the park that will give you more privacy and let you cook your own meals. For instance, this charming cottage in Port Angeles is an excellent option for a base!

Not quite what you’re looking for? Click here to browse other places to stay in Olympic National Park!

Beautiful Rialto Beach

Day 3 – Oregon Coast

The cute and quaint coastal town of Astoria is a favorite getaway for a quiet weekend — it is actually the oldest city in Oregon, founded in 1811.

The Astoria Column is one of the most famous sites. It sits atop a hill overlooking the town. The column is covered in historical depictions of the region. For another look into local history, stop at the Columbia River Maritime Museum.

The Columbia River divides Washington from Oregon and was a critical part of the area’s economy many years ago. The museum details local fishing, shipping, and military history. 

No road trip through the PNW is complete without exploring the coast, so make sure to pay Cannon Beach a visit on your way to Portland . Cannon Beach is home to Haystack Rock, one of the most iconic sites along the coast. Take a hike through Ecola State Park or visit Arch Cape.

These are areas that will get you away from the crowds as Cannon Beach does tend to see a lot of visitors, especially during the summer months. Make sure to try local seafood to round out your Oregon coast visit . 

Plan to spend your third day driving down the coast to Portland, where you’ll spend your next two nights. As another major tourist destination in the Pacific Northwest, there are countless places to rest your head in this hip city.

Beautiful coastline in Ecola State Park

Where to Stay in Portland

The Society Hotel – Centrally located close to all the major attractions of the city, this hotel is a perfect mid-range option. There are several rooms to choose from and there is also a restaurant and bar on site.

Kimpton Riverplace Hotel – If you’d prefer luxury accommodation during your stay in Portland then this hotel is a fantastic option. Located on the banks of the Willamette River, they offer a range of luxe rooms with all the amenities you would expect.

Private Rental — If you would rather have a bit of privacy and be able to cook your own meals, then a private apartment might be a good option for you. There are a number of great properties to choose from, like this quaint, centrally located cottage .

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

Day 4 – Portland, Oregon

Portland is the other main city in the Pacific Northwest and well worth a visit. Though spending two days in Portland is probably most ideal, you can still cover quite a bit of ground in just one day, as well.

The city’s mantra “keep Portland weird” rings true as you explore everything the city has to offer. Food and hikes are local favorites. There are neighborhoods throughout Portland that have the best food and nightlife, so make sure you research them before choosing where to spend your time.

Powell’s bookstore, Pittock Mansion, the Japanese Gardens, and more are excellent ways to spend a day. If you’re looking for a quiet way to spend an afternoon, consider a picnic in Laurelhurst Park. 

Portland comes alive at night!

Day 5 – Mt. Hood & Bend

If you drive just east of Portland, you’ll quickly arrive at Mt. Hood National Forest. You most likely saw Mt. Hood from Portland if it was a clear day, you might’ve also caught a glimpse of Mount St. Helens. Mt. Hood National Forest is filled with hikes of varying difficulty and camping.

The historic Timberline Lodge is worth a visit even if you’re not staying the night. Take a short hike to Trillium Lake or tackle a more strenuous hike up the side of the mountain. During the winter, Mt. Hood Meadows and Timberline are two popular ski areas. 

Bend, Oregon is a great place to stop, refuel, and restock your snacks while exploring a central Oregon city – and there are also plenty of places to explore when driving from Portland to Bend .

Bend is known for its breweries, so take your pick and have lunch at one. The Deschutes River runs through the city and offers a much-needed relief from the heat during the summer.

During winter, Mt. Bachelor is a favored spot for outdoor activities. During your time in Bend, you can choose to stick to the city shops and restaurants or venture out to Pilot Butte or Smith Rock State Park for some time outside. 

You also could use this day to explore the highlights along the Columbia River Gorge, including the beautiful Multnomah Falls.

Driving towards Mount Hood

Where to Stay in Bend

Hampton Inn & Suites – If you’re after a basic clean hotel, then this is certainly a great option. Offering a range of different rooms in a central location, they have breakfast included daily and a hot tub and fitness centre for guests to use.

Oxford Hotel – This locally run and eco-friendly boutique hotel is an excellent option for spending the night in Bend. They offer several different types of rooms in a central location with great facilities. A superb breakfast is available each morning.

Private Rental – If you value your privacy and would rather stay in a private rental in Bend than a hotel, then are several options such as this historic home in central Bend .

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

City of Bend with Mt Hood in the background

Day 6 – John Day Fossil Beds, Painted Hills & Umpqua National Forest

The John Day Fossil Beds are filled with striped hills and ancient remnants of many years ago. These colorful rock formations capture the history of the region. It’s one of the richest fossil beds in North America and a fun spot to visit for those traveling with small children.

Sit at an outlook to enjoy the view or tie up your hiking shoes to take a walk through these rolling hills. You can learn how creatures that once walked the earth here as well as climate changes while you explore. 

The Painted Hills and John Day Fossil Beds go hand-in-hand. Oregon’s Painted Hills are one of three units of John Day and perhaps one of the most recognizable. It’s hard to miss the towering hills striped with reds, browns, and yellows–colors that look like they’ve been painted on.

In total, the area is 3,132 acres, giving you ample space to explore and step away from the crowds if you desire. The Painted Hills are listed as one of the Seven Wonders of Oregon, so maybe you want to challenge yourself to visit as many wonders as possible during your trip. 

Next, head to the Umpqua National Forest. Within the forest, you’ll find waterfalls — we recommend paying Toketee Falls a visit, and several trails.

The forest covers 983,126 acres across three southern Oregon counties. Camping here during the summer is highly recommended.

There are several campgrounds that you can book in advance as well as many that are first come first serve, so they can better fit in your Pacific Northwest road trip itinerary. Take a break from the crowds and cities by spending a day exploring Umpqua National Forest. 

Day 7 – Umpqua Hot Springs & Crater Lake National Park

Seated in the Umpqua National Forest are the river’s hot springs. Visitors park in a designated parking lot before hiking a short and steep hike to the pools. Each pool is about the size of an average adult, making them ideal for lounging.

They are carved into the side of a hill and the stone around the pools do tend to get slippery, so make sure you wear proper shoes and remain cautious of where you’re stepping. The crowds at the pools tend to be a hit or miss. A weekend day usually draws more crowds than a midweek visit, so try to build your itinerary according to your preferences.

The Umpqua Hot Springs provide a nice place to rest and relax toward the end of your PNW road trip. 

Finally, it’s time to head to Crater Lake . As the only national park in Oregon, Crater Lake is a must-see during your road trip through the Pacific Northwest. Nearly 8,000 years old, a volcanic explosion rocked the area. The result was a 6,173-foot lake filled with crystal clear water that makes it appear a vibrant blue.

It’s worth visiting the park any time of year, but winters bring intense snowpack that may close roads and summer risks wildfires that can close the park. However, on a clear summer day, Crater Lake is unlike any place you’ve visited before. 

Beautiful Crater Lake

Have More Time?

We highly recommend venturing into Idaho and western Montana, or even into British Columbia – in fact, there are plenty of place to visit on the drive from Seattle to Vancouver .

If you have more time, try spending an extra day or two in the national parks and cities like Portland or Seattle . There is a lot to see during your 7-day Pacific Northwest road trip, so be sure to plan a trip that works for the speed you want to travel at. 

Take a look at a few highlights to add to your itinerary should you have some time to spare.

Yamhill-Carlton 

Here is a recommendation for those who enjoy wine tasting. The Yamhill-Carlton area is a rising player in the wine industry. Wineries here are specifically known for their Pinot Noirs and Chardonnays.

Spend a day exploring a few local wineries and enjoying the lush green rolling hills of Yamhill-Carlton. There are also several wine festivals throughout the summer that are worth the visit if your itinerary aligns. 

The Enchantments

If you’re looking for a challenging hike to round out your time in the PNW, look no further than the Enchantments. You can get permits to camp at the top of the pass, but they are highly competitive. Many people opt to thru-hike the area.

If you’re not interested in a 20-mile day hike with substantial elevation gain, you can hike up to Colchuck Lake to take in the bright blue water and snowy peaks. It’s the most picturesque section of the hike and a favorite by those who make the trek up to see. 

North Cascades National Park

“The North Cascades are calling!” Located just north of Leavenworth are the North Cascades . These impressive mountains are loaded with hikes and vantage points that welcome visitors wholeheartedly.

With more than 3,000 glaciers, bright blue lakes, and snow-kissed peaks, these mountains are well worth the visit. Make sure to explore which hikes you’re interested in doing prior to arrival as some require permits.

The North Cascades are paradise for backcountry hikers. Winter severely limits which parts of the park you can access, so visiting during summer is recommended. Early summer avoids the late summer heat waves and there’s still some snow on the mountains. 

Stunning North Cascades National Park

Whether you have five days, seven days, or more, the Pacific Northwest has a little something for everyone. With so much natural space to explore, unique cities, and geological wonders, it’s hard to decide what to visit first.

Use this route to guide your road trip decisions, but remember to create a trip that caters to your interests and you’re certain to have an unforgettable Pacific Northwest itinerary. 

Are you planning a trip to the Pacific Northwest? Have any questions? Let us know in the comments!

travel blog portland oregon

Related Posts:

Hurricane Ridge in Olympic National Park

Olympic National Park vs Mt. Rainier: Which to Visit?

Columbia River Gorge along the i-84

10 Best Stops on a Portland to Boise Drive

Heceta Head Lighthouse on the Oregon Coast

The Perfect 3 to 5-Day Oregon Coast Itinerary

Avatar photo

About Audrey Webster

Audrey Webster is a writer for The World Was Here First. She is an Oregon native who has visited countries across the globe and currently spends her weekends exploring the Pacific Northwest and surrounding states. Her approach to traveling combines exploring famous tourist sites and wandering off the beaten path to discover new destinations.

Thank you. We like your Pacific Northwest Itinerary, Seattle to Portland and plan to visit our grandson in Eugene on this trip and want to link to scenic route including Mt. Rainer, Mt. St. Helen’s, Crater Lake, Mt. Hood and more. If there is a planning group to contact to help plan a route this would be helpful with hotels and b&b’s in our budget. 3-4 weeks duration.

Leave a Comment Cancel reply

Stacker

The 30 things everyone should do at least once in Portland, Oregon

Posted: March 24, 2024 | Last updated: March 24, 2024

<p><a href="https://www.stacker.com/oregon/portlandor">Stacker</a> compiled a list of the highest rated things to do in Portland, Oregon on <a href="https://www.tripadvisor.com/">Tripadvisor</a>. Tripadvisor rankings factor in the average rating and number of reviews.</p>

Highest-rated things to do in Portland, Oregon, according to Tripadvisor

Stacker compiled a list of the highest rated things to do in Portland, Oregon on Tripadvisor . Tripadvisor rankings factor in the average rating and number of reviews.

<p>- Rating: 4.5 / 5 (5,647)<br>- Type of activity: Gardens<br>- Address: 400 SW Kingston Ave, Portland, OR 97205-5883<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d126570-Reviews-International_Rose_Test_Garden-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#30. International Rose Test Garden

- Rating: 4.5 / 5 (5,647) - Type of activity: Gardens - Address: 400 SW Kingston Ave, Portland, OR 97205-5883 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (6,280)<br>- Type of activity: Gardens<br>- Address: 611 SW Kingston Ave, Portland, OR 97205-5886<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d126571-Reviews-Portland_Japanese_Garden-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#29. Portland Japanese Garden

- Rating: 4.5 / 5 (6,280) - Type of activity: Gardens - Address: 611 SW Kingston Ave, Portland, OR 97205-5886 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (2,540)<br>- Type of activity: Gardens<br>- Address: 239 NW Everett St, Portland, OR 97209-3957<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d196850-Reviews-Lan_Su_Chinese_Garden-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#28. Lan Su Chinese Garden

- Rating: 4.5 / 5 (2,540) - Type of activity: Gardens - Address: 239 NW Everett St, Portland, OR 97209-3957 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (1,556)<br>- Type of activity: Zoos • Parks<br>- Address: 4033 SW Canyon Rd, Portland, OR 97221-2760<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d102995-Reviews-Washington_Park-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#27. Washington Park

- Rating: 4.5 / 5 (1,556) - Type of activity: Zoos • Parks - Address: 4033 SW Canyon Rd, Portland, OR 97221-2760 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (2,562)<br>- Type of activity: Points of Interest & Landmarks • Architectural Buildings<br>- Address: 3229 NW Pittock Dr, Portland, OR 97210-5099<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d126572-Reviews-Pittock_Mansion-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#26. Pittock Mansion

- Rating: 4.5 / 5 (2,562) - Type of activity: Points of Interest & Landmarks • Architectural Buildings - Address: 3229 NW Pittock Dr, Portland, OR 97210-5099 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (1,327)<br>- Type of activity: Forests • Religious Sites<br>- Address: Northeast Sandy Blvd. & 85th St. (GPS 8840 NE Skidmore), Portland, OR 97220<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d144023-Reviews-The_Grotto_National_Sanctuary_of_Our_Sorrowful_Mother-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#25. The Grotto - National Sanctuary of Our Sorrowful Mother

- Rating: 4.5 / 5 (1,327) - Type of activity: Forests • Religious Sites - Address: Northeast Sandy Blvd. & 85th St. (GPS 8840 NE Skidmore), Portland, OR 97220 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (897)<br>- Type of activity: Scenic Drives • Valleys<br>- Address: not available<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d264362-Reviews-Willamette_Valley-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#24. Willamette Valley

- Rating: 4.5 / 5 (897) - Type of activity: Scenic Drives • Valleys - Address: not available - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (726)<br>- Type of activity: Parks • Hiking Trails<br>- Address: NW 29 & Upshur to Newberry Road, Portland, OR 97210<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d532090-Reviews-Forest_Park-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#23. Forest Park

- Rating: 4.5 / 5 (726) - Type of activity: Parks • Hiking Trails - Address: NW 29 & Upshur to Newberry Road, Portland, OR 97210 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (2,601)<br>- Type of activity: Zoos<br>- Address: 4001 SW Canyon Rd, Portland, OR 97221-2799<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d138147-Reviews-Oregon_Zoo-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#22. Oregon Zoo

- Rating: 4.5 / 5 (2,601) - Type of activity: Zoos - Address: 4001 SW Canyon Rd, Portland, OR 97221-2799 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (1,656)<br>- Type of activity: Speciality Museums<br>- Address: 1945 SE Water Ave, Portland, OR 97214-3356<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d123169-Reviews-Oregon_Museum_of_Science_and_Industry-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#21. Oregon Museum of Science and Industry

- Rating: 4.5 / 5 (1,656) - Type of activity: Speciality Museums - Address: 1945 SE Water Ave, Portland, OR 97214-3356 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (1,161)<br>- Type of activity: Speciality Museums<br>- Address: 1219 SW Park Ave, Portland, OR 97205-2430<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d126564-Reviews-Portland_Art_Museum-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#20. Portland Art Museum

- Rating: 4.5 / 5 (1,161) - Type of activity: Speciality Museums - Address: 1219 SW Park Ave, Portland, OR 97205-2430 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (367)<br>- Type of activity: Nature & Wildlife Areas • Parks<br>- Address: 4000 SW Fairview Blvd Fisherlane, Portland, OR 97221-2706<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d137881-Reviews-Hoyt_Arboretum-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#19. Hoyt Arboretum

- Rating: 4.5 / 5 (367) - Type of activity: Nature & Wildlife Areas • Parks - Address: 4000 SW Fairview Blvd Fisherlane, Portland, OR 97221-2706 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (582)<br>- Type of activity: Bridges<br>- Address: U.S. Highway 30, Portland, OR 97210<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d562020-Reviews-St_Johns_Bridge-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#18. St. Johns Bridge

- Rating: 4.5 / 5 (582) - Type of activity: Bridges - Address: U.S. Highway 30, Portland, OR 97210 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (1,111)<br>- Type of activity: Flea & Street Markets<br>- Address: 108 W Burnside St, Portland, OR 97209-4008<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d126746-Reviews-Portland_Saturday_Market-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#17. Portland Saturday Market

- Rating: 4.5 / 5 (1,111) - Type of activity: Flea & Street Markets - Address: 108 W Burnside St, Portland, OR 97209-4008 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (445)<br>- Type of activity: Gardens<br>- Address: 5801 SE 28th Ave, Portland, OR 97214<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d138002-Reviews-Crystal_Springs_Rhododendron_Garden-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#16. Crystal Springs Rhododendron Garden

- Rating: 4.5 / 5 (445) - Type of activity: Gardens - Address: 5801 SE 28th Ave, Portland, OR 97214 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (229)<br>- Type of activity: Farmers Markets<br>- Address: 240 N Broadway Suite 129, Portland, OR 97227-1879<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d1146567-Reviews-Portland_Farmers_Market-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#15. Portland Farmers Market

- Rating: 4.5 / 5 (229) - Type of activity: Farmers Markets - Address: 240 N Broadway Suite 129, Portland, OR 97227-1879 - Read more on Tripadvisor

<p>- Rating: 4.0 / 5 (988)<br>- Type of activity: Trams<br>- Address: 3303 S Bond Ave, Portland, OR 97239<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d653867-Reviews-Portland_Aerial_Tram-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#14. Portland Aerial Tram

- Rating: 4.0 / 5 (988) - Type of activity: Trams - Address: 3303 S Bond Ave, Portland, OR 97239 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (1,020)<br>- Type of activity: Public Transportation Systems<br>- Address: Gresham to Hillsboro east-west through downtown, Portland, OR 97209<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d565283-Reviews-Metropolitan_Area_Express_MAX-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#13. Metropolitan Area Express (MAX)

- Rating: 4.5 / 5 (1,020) - Type of activity: Public Transportation Systems - Address: Gresham to Hillsboro east-west through downtown, Portland, OR 97209 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (201)<br>- Type of activity: Parks • Gardens<br>- Address: 700 N Rosa Parks Way, Portland, OR 97217-2064<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d563196-Reviews-Peninsula_Park_and_Rose_Gardens-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#12. Peninsula Park and Rose Gardens

- Rating: 4.5 / 5 (201) - Type of activity: Parks • Gardens - Address: 700 N Rosa Parks Way, Portland, OR 97217-2064 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (1,131)<br>- Type of activity: Neighborhoods<br>- Address: 404 NW 10th Ave # LL1, Portland, OR 97209-3184<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d146839-Reviews-Pearl_District-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#11. Pearl District

- Rating: 4.5 / 5 (1,131) - Type of activity: Neighborhoods - Address: 404 NW 10th Ave # LL1, Portland, OR 97209-3184 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (258)<br>- Type of activity: Parks<br>- Address: Southeast 39th Avenue, Portland, OR 97214<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d565310-Reviews-Laurelhurst_Park-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#10. Laurelhurst Park

- Rating: 4.5 / 5 (258) - Type of activity: Parks - Address: Southeast 39th Avenue, Portland, OR 97214 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (452)<br>- Type of activity: History Museums<br>- Address: 1200 SW Park Ave, Portland, OR 97205-2483<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d126565-Reviews-Oregon_Historical_Society-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#9. Oregon Historical Society

- Rating: 4.5 / 5 (452) - Type of activity: History Museums - Address: 1200 SW Park Ave, Portland, OR 97205-2483 - Read more on Tripadvisor

<p>- Rating: 5.0 / 5 (192)<br>- Type of activity: Historic Sites • Theaters<br>- Address: 128 NW 11th Ave Portland Center Stage, Portland, OR 97209-4160<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d1513658-Reviews-Portland_Center_Stage_at_The_Armory-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#8. Portland Center Stage at The Armory

- Rating: 5.0 / 5 (192) - Type of activity: Historic Sites • Theaters - Address: 128 NW 11th Ave Portland Center Stage, Portland, OR 97209-4160 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (177)<br>- Type of activity: Bridges<br>- Address: Crosses the Willamette River, Portland, OR 97201<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d8687470-Reviews-Tilikum_Crossing-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#7. Tilikum Crossing

- Rating: 4.5 / 5 (177) - Type of activity: Bridges - Address: Crosses the Willamette River, Portland, OR 97201 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (282)<br>- Type of activity: Mountains • Parks<br>- Address: SE 69th and Belmont Street, Portland, OR 97215<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d137885-Reviews-Mount_Tabor_Park-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#6. Mount Tabor Park

- Rating: 4.5 / 5 (282) - Type of activity: Mountains • Parks - Address: SE 69th and Belmont Street, Portland, OR 97215 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (216)<br>- Type of activity: Monuments & Statues<br>- Address: Washington Park, Portland, OR 97207<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d1626551-Reviews-Oregon_Holocaust_Memorial-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#5. Oregon Holocaust Memorial

- Rating: 4.5 / 5 (216) - Type of activity: Monuments & Statues - Address: Washington Park, Portland, OR 97207 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (306)<br>- Type of activity: Libraries<br>- Address: 801 SW 10th Ave, Portland, OR 97205-2520<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d532080-Reviews-Multnomah_County_Central_Library-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#4. Multnomah County Central Library

- Rating: 4.5 / 5 (306) - Type of activity: Libraries - Address: 801 SW 10th Ave, Portland, OR 97205-2520 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (176)<br>- Type of activity: State Parks<br>- Address: 11321 SW Terwilliger Blvd, Portland, OR 97219-7704<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d137924-Reviews-Tryon_Creek_State_Natural_Area-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#3. Tryon Creek State Natural Area

- Rating: 4.5 / 5 (176) - Type of activity: State Parks - Address: 11321 SW Terwilliger Blvd, Portland, OR 97219-7704 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (162)<br>- Type of activity: Neighborhoods • Historic Walking Areas<br>- Address: Northwest 23rd Avenue and Northwest 21st Avenue NW Everett St to NW Thurman St, Portland, OR 97210<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d102992-Reviews-Northwest_Nob_Hill-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#2. Northwest (Nob Hill)

- Rating: 4.5 / 5 (162) - Type of activity: Neighborhoods • Historic Walking Areas - Address: Northwest 23rd Avenue and Northwest 21st Avenue NW Everett St to NW Thurman St, Portland, OR 97210 - Read more on Tripadvisor

<p>- Rating: 4.5 / 5 (217)<br>- Type of activity: Neighborhoods • Points of Interest & Landmarks<br>- Address: 1722 NE Alberta St, Portland, OR 97211-5802<br>- <a href="https://www.tripadvisor.com/Attraction_Review-g52024-d4559709-Reviews-Alberta_Street-Portland_Oregon.html">Read more on Tripadvisor</a></p>

#1. Alberta Street

- Rating: 4.5 / 5 (217) - Type of activity: Neighborhoods • Points of Interest & Landmarks - Address: 1722 NE Alberta St, Portland, OR 97211-5802 - Read more on Tripadvisor

More for You

FILE - Kentucky Senate President Robert Stivers presides over a session at the Kentucky State Capitol in Frankfort, Ky., Tuesday, March 26, 2024. Kentucky lawmakers on Thursday, March 28, gave final approval to a bill stripping the state's Democratic governor of any role in picking someone to occupy a U.S. Senate seat if a vacancy occurred in the home state of 82-year-old Senate Republican leader Mitch McConnell.(AP Photo/Timothy D. Easley, File)

Republican-passed bill removes role of Democratic governor if Senate vacancy occurs in Kentucky

Putin Issues F-16 Warning

Putin Issues F-16 Warning

travel blog portland oregon

Jerry Seinfeld's Star-Studded “Unfrosted” Trailer Presents a Silly Pop-Tarts Origin Story

Ginormous dogs!

25 Large Dog Breeds That Make Great Pets

Woman banned from Planet Fitness for photographing trans member takes stand s firm: 'Here for the long haul'

Woman banned from Planet Fitness for photographing trans member stands firm: 'Here for the long haul'

Shaquille O’Neal trolls Ben Simmons: “I want to learn how you can make $80 million and play 55 games”

Shaquille O’Neal trolls Ben Simmons: “I want to learn how you can make $80 million and play 55 games”

Frank Meeink, once a white supremacist gang leader, is now an observant Jew who studies the Torah

Neo-Nazi who inspired American History X is now an orthodox Jew

Chinese Coast Guard Sprays Philippine Supply Boat

Injured Allied Navy Sailors Given Combat Medals After China Clash

Section 31: First Image of Michelle Yeoh in New Star Trek Movie Released

Section 31: First Image of Michelle Yeoh in New Star Trek Movie Released

Two Dogs Playing In The Park,hakadal,norway

52 Fun Facts About Dogs You Never Knew

Pet owner has 13 golden retrievers: 'Happiness is an understatement'

Biden's surprise campaign boost has changed 2024 race

Windows 10 update stress

How to speed up your computer without spending money or upgrading hardware

Photo: Russian Federation uses chemical weapons on the battlefield (facebook.com)

Russians employ chemical weapons on battlefield in Ukraine

This Country Icon Is Joining The Voice as Season 25 Mega Mentor

This Country Icon Is Joining The Voice as Season 25 Mega Mentor

‘A Gentleman in Moscow' Review: Ewan McGregor and Mary Elizabeth Winstead Shine in Showtime's Gently Restrained Period Drama

‘A Gentleman in Moscow' Review: Ewan McGregor and Mary Elizabeth Winstead Shine in Showtime's Gently Restrained Period Drama

Missing a doctor's appointment may trigger a 'no-show' fee of up to $100. Is that fair? Experts weigh in

I was charged $150 for missing a doctor's appointment. Turns out these fees are on the rise

Condensation forms around a US Air Force F-22 Raptor fighter in flight. The fighter, probably the most sophisticated and powerful in the world, is to receive a final upgrade to ensure it remains dominant against 'near peer' enemies such as China

World’s best fighter jet gets an upgrade for war against China

We're paws-itive you'll love these cute white dog breeds

20 Beautiful White Dog Breeds—and How to Keep Them Clean

Ryan Clark: Steelers Are Operating in Un-Steelers-Like Way

Ryan Clark: Steelers Are Operating in Un-Steelers-Like Way

Liz Cheney Donald Trump Supreme Court

Liz Cheney Gives Warning to Supreme Court

  • Enable Accessibility

User Picture

  • 00800 0310 21 21 1-855-577-9489 1-877-288-3037 1-877-288-3037 1-877-474-2969
  • | NCL Travel Blog">11-Reasons to Cruise to Alaska this Summer | NCL Travel Blog
  • | Norwegian Cruise Line">14-Day Authentic Alaska - Northbound Cruise Tour | Norwegian Cruise Line
  • | Deck Plans | Norwegian Cruise Line">14-Day Authentic Alaska - Southbound Cruise Tour | Deck Plans | Norwegian Cruise Line
  • | Norwegian Cruise Line">20-Day Transpacific from Tokyo (Yokohama) & Alaska | Norwegian Cruise Line
  • | NCL Travel Blog">11 Reasons to Cruise to Alaska this Summer | NCL Travel Blog
  • View All Results
  • Preferences
  • Latitudes Rewards
  • Special Offers
  • Personalised Recommendations
  • Make reservations before you cruise
  • 1 (current)

* Terms & Conditions Package not available on sailings less than 5 days or charter sailings.

Norwegian Escape

Explore Canada & New England: 2024 Cruises from Boston

Boston skyline and harbor at night

Boston, Massachusetts, with a history stretching back to the 1600s, is one of the oldest cities in the United States, offering plenty to see and do . It's also a tremendous port of call from which Norwegian Cruise Line provides numerous opportunities to embark. So, if you're looking into cruises in 2024, let us guide you through all the itineraries and ports you could incorporate into your family vacation when departing from Boston .

Ready to start planning? Explore all Boston cruises .

Horseshoe Bay, Southampton, Bermuda

2024 Bermuda Cruises from Boston

Around 770 miles south of Boston and 900 miles north of The Caribbean, Bermuda is home to a wealth of beautiful pink-sand beaches, green spaces, and opportunities for golfing, diving, caving, and historical sightseeing.

Check out these exciting cruise vacations that Norwegian has to offer in 2024:

Explore Bermuda & Maine on Norwegian Gem

Norwegian Gem will take you from Boston to Bermuda before looping around to Maine and back to Boston during a seven-day cruise . Embark on a late Friday afternoon and cruise the stunning Atlantic Ocean on Saturday. On Sunday, around noon, disembark at the Royal Naval Dockyard on the West End, the marine hub of the island.

This marks the start of three days and two nights on this breathtaking island. You can start your exploration by sticking around the West End and taking advantage of the azure waters with many water sports around the harbor. Or, simply enjoy the crystalline environment as a backdrop while checking out the market and shops.

RELATED CRUISES: 7-Day Bermuda Cruise from Boston 7-Day Canada & New England Cruise: Boston to Quebec City 7-Day Canada & New England Cruise: Nova Scotia & Saint John

On day two, you have plenty of time to explore the pleasures of Bermuda, and Norwegian's shore excursions can ensure the experience is hassle-free. Feeling adventuresome? Check out the island's caves and explore a shipwreck. More the easygoing type? Enjoy a traditional English tea service, hear fascinating stories about Bermuda's history, and visit the many museums with centuries of tales to tell. With a free morning and early afternoon on the third day, you can easily fill in any gaps in your itinerary.

After another day at sea, you'll land in Bar Harbor, Maine, a coastal Northeast wonder. With its charming, tranquil scenery and fresh seafood, this port is the perfect setting to wind down from the thrills of the previous six days. Then Norwegian Gem will return to Boston that evening, capping a luxurious week in the North Atlantic.

Visit Bermuda on Norwegian Gem

If you want more time in Bermuda, Norwegian offers a seven-day, two-port-of-call cruise from Boston to the Royal Naval Dockyard and back again. Leaving on Friday, you'll reach Bermuda on Sunday morning to enjoy the first of four days and three nights on the island. With a relaxed itinerary, you'll have ample time to take in the sun, water, and luxurious surroundings at your own pace.

Aerial view of Halifax, Nova Scotia, Canada

2024 Canada & New England Cruises

In the heat of summer and the dragging humidity of early fall, many people choose to escape the heat for cooler climates. If you're one of them, a Norwegian cruise vacation to Canada and New England could be your perfect family getaway.

Explore Canada & New England on Norwegian Gem

Seven ports in seven days — are you up for it? After leaving Boston, spend a pleasant day among the natural opulence of Bar Harbor, Maine, before heading into Canadian waters, where the first stop is Halifax, Nova Scotia, remarkable for its thunderous rugged coastline as well as an affluence of wine, cider, and fresh seafood. From there, it's Sydney on the Nova Scotian island of Cape Breton and then Charlottetown on Prince Edward Island, both spectacular destinations for scenic tours.

After a day at sea, you enter Québec, beginning in Saguenay and culminating in Québec City. From there, you'll board a coach for the grand city of Montreal, where you can traverse the historic metropolis at your leisure.

Portland Lighthouse, Portland, Maine, United States of America

Discover Halifax & Portland on Norwegian Jade

On this seven-day cruise , Norwegian Jade embarks from Boston and disembarks at Portland, Maine, providing a morning and early afternoon to explore the city's stellar waterfront, arts districts, museums, and shops. This journey includes three days in Nova Scotia and Prince Edward Island, followed by a visit to the rugged beauty of Newfoundland. You'll find a wealth of historic sites, museums, and charming villages here, as well as opportunities to spot whales and icebergs.

As you can see, Boston is the perfect port to embark on an exciting adventure. Which cruise vacation will it be for you?

Be sure to sign up for Norwegian's cruise deals . You'll get the latest specials and offers delivered to your inbox.

IMAGES

  1. Portland, Oregon 2021: Top 10 Tours & Activities (with Photos)

    travel blog portland oregon

  2. The VERY BEST of What to Do in Portland, Oregon: 40 Fun Things to Do in

    travel blog portland oregon

  3. 36 HOUR TRAVEL GUIDE TO PORTLAND, OREGON

    travel blog portland oregon

  4. 25 Things To Do In Portland Oregon

    travel blog portland oregon

  5. Your Trip to Portland, Oregon: The Complete Guide

    travel blog portland oregon

  6. 15 Things To Do In Portland Oregon: The Ultimate Bucket List

    travel blog portland oregon

COMMENTS

  1. 3 Days in Portland, Oregon: The Perfect Weekend Portland Itinerary

    I've got the perfect 3 day Portland itinerary for you - including the best food, views, and some great nature spots outside the city! Portland, Oregon is best known for its delectable donuts, snobby coffee culture, orgasmic food, and, of course, for being weird. It is their slogan after all! 3 days in Portland will give you enough time to ...

  2. Ultimate Portland Travel Guide: The Best of What to do in Portland

    Columbia River Gorge. Columbia River Gorge is a designated National Scenic Area just 40 minutes from downtown Portland. There are plenty of hikes to be enjoyed, including scenic waterfalls and mountain bike trails. One of the most popular sights is the Multnomah waterfall, which can be seen from the roadside.

  3. The PERFECT 3 Days in Portland Itinerary (2024 Update)

    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.

  4. 14 Things to See and Do in Portland, Oregon

    There are permanent exhibitions, rotating temporary galleries, and an outdoor sculpture park. There's a lot of variety here, so be sure to check the website to see what's on during your visit. 1219 SW Park Ave, +1 503-226-2811, portlandartmuseum.org. Open Wednesday-Sunday 10am-5pm. Admission is $25 USD.

  5. Home

    Hey there. I'm Antonina and I'm glad you found your way to my website. Embrace Someplace is a Portland-based travel blog that provides helpful posts on Portland and Oregon's unparalleled natural wonders.

  6. 3 Days in Portland OR: The Ultimate Weekend in Portland Itinerary

    Table of Contents [ hide] 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.

  7. EPIC Portland Travel Guide (Budget Tips • 2024)

    1.Lower Macleay Trail, 2.Wildwood Trail, 3.Pittock Mansion, 4.Japanese Gardens, 5.Hoyt Arboretum. Today, we head for the hills! The West Hills to be exact. On the final leg of this Portland travel guide, we're going for a walk in one of the city's most adored places, Forest Park.

  8. PORTLAND Itinerary • MUST READ! (2024 Guide)

    Portland Itinerary: Day 3 and Beyond. 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.

  9. Portland Itinerary: Plan a Perfect Weekend in Portland, Oregon

    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.

  10. How to Spend 1 day in Portland,Oregon

    The history of the rose garden is equally fascinating. Originally started in 1915 by Jesse Currey, (an Oregon Journal editor and rose hobbyist), the rose garden was created in an effort to preserve roses susceptible to eradication during World War I. Location: 400 SW Kingston Ave, Portland, OR 97205.

  11. Top Things to Do in Portland in a Weekend • The Blonde Abroad

    Day Trip to Waterfalls. East of Portland is the stunning Columbia River Gorge, home to many beautiful hiking trails and waterfalls. Multnomah Falls is by far the local and visitor's favorite. This two-tiered cascade plunges 620 feet and is photo worthy all year long.

  12. Perfect Itinerary for One Day in Portland, Oregon

    International Rose Test Garden. The International Rose Test Garden is a free attraction in Washington Park that you can't miss during one day in Portland, Oregon. In this garden, you will find more than 10,000 rose bushes representing 600+ rose varieties.

  13. How to Spend One Perfect Day in Portland, Oregon

    Drinks. Dessert/Treats - DONUTS. One Day in Portland Itinerary. Start Your Day with Brunch at the Screen Door. Visit the Incredible Powell's City of Books. Explore Washington Park. Wander Around the Japanese Garden. Be Amazed by the International Rose Test Garden. Go Back in Time at the Pittock Mansion.

  14. The Ultimate Guide To Portland In A Weekend: Eat, Stay & Play

    Christy Woodrow is a travel photographer and professional blogger based in San Diego, California. She started this adventure travel blog in 2010 to provide trip ideas and helpful travel tips for people with limited vacation time. Follow her adventures by signing up for weekly emails or read more about her on our about page.

  15. Magical Oregon Road Trip: Steal this Itinerary!

    Less than 20 miles east of Portland, the Columbia River Gorge stretches over 80 miles through a canyon reaching up to 4,000 deep in places as it winds along the Columbia River, following the Oregon/Washington border. This stretch of canyon has been designated a National Scenic Area and is the largest in America.

  16. The Ultimate Oregon Road Trip: Itinerary Inspiration and Must-See Stops

    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.

  17. 23 Fun Things to Do in Portland, Oregon

    The Willamette Valley is known for its pinot noirs. Tillamook (73 miles away): Visit the famous Tillamook Creamery, go for a hike in the Tillamook Forest and more. Cannon Beach (80 miles away ...

  18. Things to do in Portland

    Cinema 21. Originally a single-screen theater and now a three-screen multiplex, Cinema 21 specializes in art-house, foreign and classic films and serves beer, wine and pizza along with concessions classics. There are hundreds of things to do in Portland. Our attractions - much like the city itself - are both unexpected and inspiring.

  19. Portland, Oregon

    Portland is known for having the amenities of a major city (such as an international airport, an efficient public transit system, major league sports teams and many museums and art galleries) and the charms of a small city (such as plentiful arts and crafts fairs, independent bookstores and local traditions like the annual Rose Festival Parade and the World Naked Bike Ride).

  20. A Perfect Weekend in Portland Oregon With These Tips From a Local

    Susan Stephens is a scientist-turned-travel-writer and a transplant from the Midwest. She has lived in Portland, Oregon for over twenty years. Her travel blog is dedicated to helping people discover the beauty of the Pacific Northwest. Please visit her website - Explorer Sue - to start planning your next Pacific Northwest adventure!

  21. Portland 6-Day Itinerary

    Escape to the indie city vibes of Portland, Oregon. From touring the sights to dining gourmet to exploring natural wonders, discover the best attractions, hotels, and things to do in Portland. ... stay, and itinerary options selected. Itineraries are only available through the reservations line at 1-833-794-1694. Travel + Leisure GO pricing is ...

  22. The Perfect 5 to 7 Day Pacific Northwest Itinerary

    Day 4 - Portland, Oregon. Portland is the other main city in the Pacific Northwest and well worth a visit. Though spending two days in Portland is probably most ideal, you can still cover quite a bit of ground in just one day, as well. The city's mantra "keep Portland weird" rings true as you explore everything the city has to offer ...

  23. The Ultimate 4-Day Oregon Coast Guide • The Blonde Abroad

    Drive carefully on Highway 101, it can be narrow and windy at times. Pack a picnic for scenic roadside meals. Avoid the crowds by planning your trip outside busy summer weekends. Be prepared for changing weather, from fog to sun to rain in a day. Bring layers including windbreakers and warm clothing.

  24. A Booklover's Guide to Portland

    While Portland is a city perhaps best known for its roses and stellar food scene, for the literary-inclined, we're noted for our celebration of independent bookstores, presses and all things writerly. Portland is even statistically more bookish than most cities, ranking higher than average when comparing bookstores per capita across the nation.

  25. Portland, Oregon

    Portland (/ ˈ p ɔːr t l ə n d / PORT-lənd) is a port city in the Pacific Northwest and the most populous city in the U.S. state of Oregon.Situated in the northwestern area of the state at the confluence of the Willamette and Columbia rivers, Portland is the county seat of Multnomah County, the most populous county in Oregon.As of 2020, Portland had a population of 652,503, making it the ...

  26. The 30 things everyone should do at least once in Portland, Oregon

    For example, if you're in a four-star hotel you can expect to pay €1.70 in tourist tax (£1.46), for rentals like Airbnb it will be €2.25 (£1.93) and for five-star hotels and luxury ...

  27. PDX to see over 800,000 spring break travelers

    Travel PDX will see more than 800,000 travelers during spring break Over 800,00 people will come through the Portland International Airport between March 22 and April 7.

  28. Explore Canada & New England: 2024 Cruises from Boston

    On this seven-day cruise, Norwegian Jade embarks from Boston and disembarks at Portland, Maine, providing a morning and early afternoon to explore the city's stellar waterfront, arts districts, museums, and shops. This journey includes three days in Nova Scotia and Prince Edward Island, followed by a visit to the rugged beauty of Newfoundland.