places to visit in gloucester ma

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15 Best Things to Do in Gloucester (MA)

Dubbed “America’s Oldest Seaport”, Gloucester was first settled by Europeans more than 400 years ago, and for all this time has been a center for the fishing industry.

From the 19th century, the moody seascapes at Cape Ann began to attract painters like Winslow Homer, and the longest-operating art colony in the United States can still be found here at Rocky Neck.

Modern Gloucester is a world-renowned summer vacation destination, and a favored place for day trips just over 30 miles from downtown Boston.

To go with a quaint downtown area, some of the best whale watching in the world, and authentic maritime heritage, Gloucester is blessed with white sandy beaches that have to be seen to be believed.

1. Good Harbor Beach

At places like Good Harbor Beach it’s easy to see what has brought artists to Gloucester for the last 170+ years.

This is most likely the best beach on the North Shore, with low rolling waves and a vast and gently pitching curve of white sand.

Just offshore is the granite mass of Salt Island, and the water recedes so far at low tide that you can walk to it across the sand. When the tide is up conditions are perfect for swimming, wading in the surf and bodyboarding.

As with Gloucester’s other premier beaches, Good Harbor Beach has lifeguards on duty from Memorial Day Weekend to Labor Day, and of course is open for you to swim at your own risk at other times of the year.

Although the beach is public, Gloucester has recently introduced an online parking reservation system for non-residents.

2. Fisherman’s Memorial Monument

A stately boulevard arcs around the harborfront on the west side of downtown Gloucester, and the promenade is an apt place for some contemplation.

Erected here in 1923 on Gloucester’s 3rd centennial is the Fisherman’s Memorial Monument, dedicated to the fisherman lost at sea.

This iconic work, by the English sculptor Leonard Craske (1880-1950), depicts a man in oilskins at the helm, evidently trying to steer through rough seas.

On a crescent of granite in front are plaques with the names of Gloucester fishermen lost at sea over the years, along with other drownings, in a list including women, children, dockworkers, engineers and vacationers.

3. Hammond Castle Museum

One interesting character from Gloucester was the inventor John Hays Hammond Jr. (1888-1965), remembered as “The Father of Remote Control”.

As well as being credited with more than 800 domestic and foreign patents, Hammond was an extensive traveler and had an eye for historic architecture.

In the 1920s he commissioned the Allen & Collens architectural firm to build the whimsical Hammond Castle as his home and laboratory.

Perched on a cliff overlooking the harbor, there are sections inspired by a 13th-century castle, a 13th-century French Gothic cathedral (Chartres) and a 15th-century chateau.

As well as being a place of work, this was all a fitting canvas for Hammond’s large collection of artifacts from Ancient Rome through the Renaissance.

Today this spellbinding complex is open to the public daily throughout the summer season, and on weekends in November and December. You can soak up the coastal views, see room after room of historic treasures and peruse Hammond’s many inventions.

4. Historic Downtown Gloucester

Tracing the Inner Harbor along the meandering Main St, Gloucester has a downtown area that is at once quaint and vibrant.

In a city famed for fishing you can bet that there are world-class seafood restaurants here, but that isn’t the limit of downtown’s dining selection, far from it.

Coffee shops and casual eateries are interspersed with antique stores, galleries, boutiques, museums and other cultural mainstays like the Cape Ann Community Cinema.

One way to get to grips with downtown’s present and past is on the Gloucester HarborWalk, a trail with 42 granite story posts throughout the historic center and along the waterfront.

If you’d like to witness Gloucester’s community spirit in full bloom be here for one of the Downtown Block Parties, shutting down Main Street for three summer nights, in July, August and September.

5. Whale Watching

Gloucester’s location, within miles of the Stellwagen Bank National Marine Sanctuary, and even closer to key feeding grounds, like Tillies Bank and Jeffreys Ledge, makes it the best place in Massachusetts, and one of the best places in the world for whale watching.

The most commonly sighted species are humpbacks, growing up to 60 feet, but you’ll also stand a great chance of seeing Minke whales (20 feet), and enormous fin whales, which are second only to blue whales in size, and have been known to reach more than 80 feet.

Sightings are pretty much guaranteed between May and October, and the main operators are Cape Ann Whale Watch (415 Main St) and 7 Seas Whale Watch (63 Rogers St).

6. Wingaersheek Beach

There’s an extraordinary public beach in western Gloucester on the northern coast of Cape Ann. Wingaersheek Beach traces the Annisquam River at its mouth for just over half a mile, giving it warm, sheltered waters that are perfect for children to splash in.

Halfway along the sandy shoreline there’s a set of granite outcrops that are easy to climb and have tidepools that kids will love to explore.

Meanwhile low tide exposes a huge sand bar that reaches out for hundreds of yards. The beach is patrolled by lifeguards every day from Memorial Day weekend to Labor Day, and as with Good Harbor Beach, parking reservations are required for non-residents.

7. Stage Fort Park

In the Western Harbor, Stage Fort Park is the site of a fishing outpost, established as early as 1623 by the Dorchester Fishing Company.

There was a fort here 1635 to 1898, and this was rebuilt for tourism in 1930, and armed with cannons, some of which are historic and some reproductions.

Stage Fort Park is now home to the Gloucester visitor center, and is a place for recreation, with a variety of sports facilities, dreamy harbor views and extensive beachfront.

One of the best public beaches in Gloucester Half Moon Beach, is right here, in a craggy and secluded cove, with shallow, rippling waters and lifeguards on duty daily from Memorial Day weekend to Labor Day.

8. Eastern Point Lighthouse

On a promontory on the east side of Gloucester Harbor there’s an active lighthouse, built in 1832 and occupied for a time by painter Winslow Homer in 1820.

Eastern Point Lighthouse is owned by the U.S. Coast Guard and is closed to the public, but it’s the location that makes a visit so worthwhile.

Shielding the entrance to the harbor here is a 2,250-foot granite jetty that is open to the public and has its own light at the end.

From here you can survey the harbor, look across the channel to grand residences like Hammond Castle, and gaze southwest to the Boston skyline.

Gloucester’s connections to the fishing industry go back 400 years and are still strong, with an annual catch worth tens of millions of dollars, and several wholesalers based in the town.

You could not hope to find a better place to enjoy seafood direct from the Atlantic, and it’s such a part of Gloucester’s identity that the town has created the self-guided Seafood Trail.

This is a curated assortment of restaurants, museums and activities to help you get in touch with the industry in Gloucester.

For dining, a few spots running the gamut from high-end to laidback are Gloucester House Restaurant (63 Rogers St), The Dining Rooms at The Castle (141 Essex Ave), Turner’s Seafood Market & Fish n’ Chips Shoppe (4 Smith St), The Studio (51 Rocky Neck Ave), Causeway Restaurant (78 Essex Ave) and Seaport Grille (6 Rowe Sq).

10. Beauport, the Sleeper-McCann House

In 1907, one of the country’s first professional interior designers, Henry Davis Sleeper (1878-1934) built this Shingle Style house in Eastern Point as a place for entertaining and a showcase for his skills.

Beauport has a magical setting, posted on a rocky ledge overlooking the harbor, and appeared in numerous early home design and architecture publications in the first decades of the 20th century.

The interior is still suffused with Sleeper’s creative flair—no two of the 40 rooms are alike, and all are enriched with his massive collection of decorative arts, from china to folk art to colored glass.

Visiting Beauport you’ll get to know Sleeper, his housekeeper, Mary Wonson, and the many interesting characters who came through these doors.

11. Cape Ann Museum

Cape Ann has been closely associated with the arts since the 19th century.

Rocky Neck in Gloucester Harbor has been the site of an art colony for more than 170 years, bringing the likes of Edward Hopper and Winslow Homer, while in the mid-20th century the Folly Grove Designers, a group of block printers, rose to prominence in Gloucester.

This heritage is documented at the Cape Ann Museum, with works by Winslow Homer, Fitz Henry Lane, Cecilia Beaux, John Sloan, and a collection of sample books and display hangings by those printers.

The museum also covers other facets of the area’s history, with rich collections for granite quarrying, and the maritime and fishing industries.

12. Maritime Gloucester

On the harborfront by Gloucester Center you’ll come across the campus for a museum preserving the town’s rich maritime heritage.

Purchased in 2000, Maritime Gloucester is on a previously neglected industrial property, including forgotten treasures like the oldest operating Marine Railway in the United States.

You can cast your eye over several historic wooden boats, and the dory shop where these traditional fishing vessels are made by hand.

Requiring a small admission fee, there are gallery spaces dedicated to the 842-square-mile Stellwagen Bank National Marine Sanctuary, maritime science education, maritime art, as well as the outdoor Seapocket Aquarium, which has interactive touch tanks.

13. Ravenswood Park

For some quiet time you could escape to this 600-acre wooded property managed by the Trustees of Reservations.

Ravenswood Park was purchased as a patchwork of woodlots by the shipowner and merchant Samuel Sawyer (1815-1899), and was left to the town to be turned into a park when he died.

The reservation has more than ten miles of broad and mostly level carriage paths to travel, with some interesting changes in topography that give far-reaching views over Gloucester Harbor.

The landscape is dotted with granite boulders, reaching impressive sizes, and low-lying areas have swamp and vernal pools.

14. Cultural Center at Rocky Neck

The Rocky Neck Art Colony (RNAC) continues to thrive, and has an evocative home, at a Carpenter Gothic meetinghouse built in 1877.

This was purchased by the colony in 2012, and now has two levels of galleries, displaying exhibitions curated by the RNAC’s Cultural Center Exhibitions Committee.

There’s a tightly packed calendar of themed and solo exhibitions that tend to run for about five weeks, while the annual juried show for RNAC members takes place at the end of the year.

The unique building is also a stage for talks, workshops, concerts and a variety of other activities.

15. Fishermen’s Wives Memorial

For hundreds of years, Gloucester’s fishing community was held up by the resilient women who were given no choice but to remain on land and keep everything together.

In tribute, the Gloucester Fishermen’s Wives Association (GFWA) erected this affecting memorial as a counterpoint to the more famous Man At the Wheel, depicting a woman looking out to the entrance of the harbor, with a boy at her waist and an infant in her left arm.

This monument was dedicated in 2001, and stands at the north end of Stage Fort Park at 107 Western Ave.

15 Best Things to Do in Gloucester (MA):

• Good Harbor Beach
• Fisherman’s Memorial Monument
• Hammond Castle Museum
• Historic Downtown Gloucester
• Whale Watching
• Wingaersheek Beach
• Stage Fort Park
• Eastern Point Lighthouse
• Beauport, the Sleeper-McCann House
• Cape Ann Museum
• Maritime Gloucester
• Ravenswood Park
• Cultural Center at Rocky Neck
• Fishermen’s Wives Memorial

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40+ Best Things To Do In Gloucester Massachusetts

Looking for the absolute best things to do in Gloucester Massachusetts? Known as “America’s Oldest Seaport,” Gloucester is an incredible town with so many wonderful activities, and today we’re sharing our favorites!

Gloucester Massachusetts is located on Cape Ann and has been one of the top fishing towns in New England for basically ever. It’s a premier summer destination (especially if you like fresh seafood!) but there are lovely parts of Gloucester any time of year.

With its rich history, stunning natural beauty, and thriving arts scene, Gloucester offers a wide range of activities and attractions for visitors to enjoy. Whether you’re interested in exploring the city’s maritime heritage, immersing yourself in the arts, or simply enjoying the picturesque landscapes, Gloucester has something to offer for everyone. It’s one of the cutest small towns in Massachusetts for a reason!

Here are some of our absolute favorite things to do in Gloucester Massachusetts!

35. Visit Gloucester Harbor:

Start your journey in Gloucester by exploring its iconic harbor, which serves as a hub of maritime activity. Stroll along the waterfront, watch fishing boats come and go, and enjoy the fresh ocean breeze. Take a boat tour or a harbor cruise to get a closer look at the city’s seafaring traditions.

The harbor is such a gorgeous place to hang out! I like to sit here with my coffee in the mornings and watch as the seaside activities begin.

34. Discover Maritime History at the Gloucester Maritime Heritage Center:

Immerse yourself in Gloucester’s seafaring past at the Gloucester Maritime Heritage Center . Learn about the city’s history as a major fishing port, explore exhibits on boatbuilding and navigation, and see artifacts from Gloucester’s fishing industry.

This is a small center but totally worth a visit if you want to get a true feel for small-town Gloucester! This is one of the best things to do in Gloucester for history buffs and is a must-do.

33. Explore Rocky Neck Art Colony:

Known as one of America’s oldest continuously operating art colonies , Rocky Neck is a vibrant neighborhood that is home to numerous art galleries, studios, and shops. Take a leisurely walk along the streets, browse unique artworks, and engage with local artists. If you want a taste of New England art then this is the place to come!

32. Visit Cape Ann Museum:

Delve into the rich history and culture of Cape Ann at the Cape Ann Museum . Discover exhibits on the area’s art, history, and maritime heritage, including the famous Gloucester Fisherman’s Memorial Statue.

With a diverse collection of artwork, including paintings, sculptures, and photographs , the museum celebrates the region’s vibrant artistic community and highlights the contributions of renowned artists associated with Cape Ann.

Its exhibits explore topics such as the area’s maritime history, the fishing industry, and the lives and works of influential artists.

31. Relax on Good Harbor Beach:

Gloucester boasts several picturesque beaches, and Good Harbor Beach is one of the most popular. Enjoy a day of sunbathing, swimming, and beachcombing on its pristine shores. The beach is also known for its stunning sunsets.

Good Harbor Beach offers ample space for sunbathing, picnicking, and playing beach games.

Good Harbor Beach is also favored for its clear and inviting waters, making it an ideal spot for swimming and boogie boarding. Lifeguards are on duty during the summer months.

Whether you’re looking to relax under the sun, take a refreshing dip in the ocean, or simply enjoy the natural beauty of the New England coastline, Good Harbor Beach offers a quintessential beach experience that captivates visitors year-round. It’s one of the best well-known beaches in the area!

30. Take a Whale Watching Tour:

Gloucester offers fantastic opportunities for whale watching due to its proximity to Stellwagen Bank National Marine Sanctuary , a prime feeding ground for whales. Hop on a whale-watching tour and witness these magnificent creatures up close.

29. Visit Hammond Castle:

Step back in time at the Hammond Castle Museum , a medieval-style castle built in the 1920s by inventor John Hays Hammond Jr. Explore the castle’s unique architecture, marvel at its collection of medieval artifacts, and enjoy panoramic views of the ocean from its towers.

28. Rent a Boat at Gloucester Boat Rental:

Explore the scenic coastline and enjoy the freedom of the open water by renting a boat from Gloucester Boat Rental . Whether you prefer a powerboat, sailboat, or kayak, you can embark on your own maritime adventure and discover hidden coves and charming islands.

27. Check out Cape Ann Marina, Home of the Wicked Tuna Fishermen:

Visit Cape Ann Marina , known for being a hub of activity for the fishermen featured on the TV show “Wicked Tuna.” Watch the fishing boats come and go, learn about the local fishing industry, and maybe even spot some of the famous tuna fishermen.

You can also grab lunch at the Mile Marker , a delicious waterfront restaurant with a lively atmosphere that overlooks the marina.

26. Tour Beauport, the Sleeper-McCann House:

Explore the historic Beauport, the Sleeper-McCann House , a beautifully preserved mansion known for its eclectic architectural styles and stunning views of Gloucester Harbor. Take a guided tour to discover the fascinating history and unique design of this remarkable house.

25. Hike in Ravenswood Park:

Nature enthusiasts will appreciate the beauty of Ravenswood Park , a 600-acre nature reserve with miles of scenic trails. Enjoy a peaceful walk through wooded areas, along babbling brooks, and around tranquil ponds. Keep an eye out for wildlife and diverse plant species.

24. Attend a Performance at Gloucester Stage Company:

Experience the vibrant performing arts scene in Gloucester by catching a play at the Gloucester Stage Company . Known for its high-quality productions, this theater company showcases a diverse range of theatrical works throughout the year.

23. Explore Dogtown Common:

Dogtown Common is a fascinating area in Gloucester that was once a settlement in the 17th and 18th centuries. Today, it is a wooded landscape with hiking trails that lead to the remnants of old cellar holes and eerie stone structures. It offers a unique blend of history and natural beauty.

22. Grab Dinner at the Beauport Hotel:

Treat yourself to a delicious meal at the Beauport Hotel’s restaurant . Enjoy waterfront dining with panoramic views of the Atlantic Ocean while indulging in a delectable menu featuring fresh seafood and other culinary delights.

21. Stroll Through Downtown Gloucester:

Take a leisurely stroll through downtown Gloucester and soak in the city’s vibrant atmosphere. Discover charming shops, art galleries, and boutiques along Main Street . Enjoy a cup of coffee at a local café, browse unique treasures, and immerse yourself in the local culture.

20. Visit the Eastern Point Lighthouse:

Make your way to the Eastern Point Lighthouse , a historic landmark perched on the rocky shores of Gloucester. Take a guided tour or simply enjoy the breathtaking views of the Atlantic Ocean. The lighthouse offers a picturesque backdrop for memorable photographs.

19. Dine on Fresh Seafood:

Gloucester is renowned for its fresh seafood, and a visit to the city wouldn’t be complete without indulging in a delicious seafood meal. Whether you’re craving lobster, clam chowder, or freshly caught fish, you’ll find plenty of excellent seafood restaurants to satisfy your appetite. Here are some of our favorite seafood restaurants on the water:

1. The Gloucester House : Situated right on the waterfront, The Gloucester House offers not only stunning views of the harbor but also a fantastic dining experience. Enjoy fresh seafood dishes while watching the boats come and go.

2. The Lobster Pool : Nestled near Folly Cove, The Lobster Pool provides outdoor seating with panoramic ocean views. Savor their delicious lobster rolls and other seafood specialties while enjoying the coastal breeze.

3. Seaport Grille : Located in downtown Gloucester, Seaport Grille offers waterfront dining along the picturesque Harbor Loop. Indulge in their seafood-focused menu while taking in the scenic views of the harbor and boats passing by.

4. Mile Marker One : Situated at the Cape Ann’s Marina Resort, Mile Marker One features a waterfront patio where you can dine overlooking the Annisquam River. Their menu offers a wide range of options, including fresh seafood, burgers, and salads.

5. The Studio Restaurant : Positioned in the Rocky Neck Art Colony, The Studio Restaurant provides waterfront dining overlooking Smith Cove. Delight in their creative menu that combines seafood and international flavors.

18. Explore Stage Fort Park:

Discover Stage Fort Park , a scenic waterfront park with stunning views of Gloucester Harbor and the Atlantic Ocean. Enjoy a picnic, go for a walk along the promenade, and explore the historic remnants of the park’s fortifications, including the famous “Balance Rock.”

17. Take a Fishing Charter:

Embrace Gloucester’s fishing heritage by chartering a fishing boat and trying your hand at catching some fish . Whether you’re an experienced angler or a beginner, the local fishing charters offer a variety of trips to suit all skill levels.

16. Take a Sunset Dinner Cruise:

Treat yourself to a romantic and unforgettable experience by embarking on a sunset dinner cruise . Cruise along the coastline, savor a delicious meal and witness the stunning colors of the sky as the sun sets over the water. It’s a perfect way to celebrate a special occasion or create lasting memories.

15. Visit the Sargent House Museum:

Step inside the beautifully preserved Sargent House Museum , a Federal-style mansion built in 1782. Learn about the life and times of one of Gloucester’s prominent families through guided tours of the elegantly furnished rooms.

If you’re looking to get a real taste of Federalist history then this is the place to come!

14. Explore Halibut Point State Park:

Just a short drive from Gloucester, Halibut Point State Park offers breathtaking coastal scenery and picturesque walking trails. Explore the park’s rugged coastline, granite quarries, and enjoy panoramic views of the Atlantic Ocean.

13. Boat Watch at the Cut Bridge:

Find a spot near the Cut Bridge, also known as the Blynman Canal Bridge, and watch as boats pass through the opening. The bridge separates the Annisquam River from Gloucester Harbor and offers a unique vantage point to observe the comings and goings of various vessels, from small fishing boats to majestic yachts.

12. Attend the Gloucester Schooner Festival:

If you happen to visit Gloucester during the Labor Day weekend, don’t miss the Gloucester Schooner Festival. This annual event celebrates the city’s seafaring heritage and features a spectacular parade of schooners, maritime exhibits, live music, and fireworks.

11. Indulge in Art and Music Festivals:

Gloucester, Massachusetts, is a vibrant hub for art and music festivals, showcasing the region’s creative spirit and cultural diversity. The city hosts a variety of festivals throughout the year, attracting both local talent and renowned artists from around the world.

Art festivals like the Gloucester HarborWalk Public Art Challenge and the Cape Ann Artisans Studio Tour provide opportunities to explore and engage with the thriving art community, showcasing works in various mediums and styles.

Music festivals such as the Gloucester Blues Festival and the Rockport Jazz Festival bring the city alive with soulful tunes and captivating performances, drawing music enthusiasts from near and far.

10. Visit Essex Shipbuilding Museum:

Located nearby in Essex, the Essex Shipbuilding Museum is one of the coolest nautical museums in the area . Explore exhibits on traditional wooden boat construction, visit the museum’s working boatyard, and learn about the craft of shipbuilding.

Housed in a historic shipyard building, the museum offers visitors a glimpse into the traditional art of wooden boatbuilding.

The museum also features a working boatyard , where visitors can witness the process of boatbuilding firsthand and even participate in workshops. With its focus on preserving the seafaring traditions of Essex, the Essex Shipbuilding Museum provides an immersive and educational experience for all ages!

9. Explore the Backshore:

The Backshore is a rugged coastal area in Gloucester known for its beautiful rocky beaches and scenic landscapes. Take a leisurely drive along Atlantic Road and stop at spots like Bass Rocks and Good Harbor Beach to enjoy the dramatic ocean views.

8. Head to Wingaersheek Beach:

Located just a short drive from Gloucester, Wingaersheek Beach is a stunning sandy beach known for its tranquil waters and natural beauty . Spend a day relaxing on the beach, building sandcastles, or taking a refreshing swim. The beach also features a scenic walking trail along the marshland.

The beach is flanked by rocky outcrops that add to its scenic charm, and during low tide, visitors can explore tidal pools and check out the marine life.

Alternatively, you can take a boat to the backside of Wingaersheek Beach for a really packed, party atmosphere!

7. Go Kayaking or Stand-Up Paddleboarding:

Experience Gloucester’s coastline from a different perspective by renting a kayak or a stand-up paddleboard . Explore the calm waters, coves, and hidden corners of the city’s shoreline while enjoying a peaceful and active adventure.

6. Visit Nearby Rockport:

Looking to visit another quaint New England town? Check out Rockport Massachusetts, only a 5-10 minute drive from Gloucester. Rockport is one of the best towns for walking around, so we recommend heading here for an afternoon of fun. But it’s even gorgeous just to drive through!

Check out our favorite things to do in Rockport here.

5. Explore the Annisquam Village:

Venture into the charming Annisquam Village, a historic district within Gloucester. Admire the picturesque New England architecture, explore quaint shops and art galleries, and enjoy a leisurely stroll along the Annisquam River.

4. Visit the Gloucester Fishermen’s Wives Memorial:

Pay homage to the brave women of Gloucester’s fishing community by visiting the Gloucester Fishermen’s Wives Memorial . Located on Stacy Boulevard, this statue honors the resilience and strength of the women who have supported their families and loved ones in the fishing industry.

3. Attend the Gloucester Block Party:

If you happen to visit Gloucester during the summer, don’t miss the Gloucester Block Party.

This lively event takes place in downtown Gloucester and features live music, food vendors, local artisans, and family-friendly activities. It’s a great opportunity to immerse yourself in the local culture and enjoy a vibrant street festival atmosphere.

2. Go Fishing off the Breakwater:

Grab your fishing gear and cast a line off the breakwater, a long stone structure that extends into Gloucester Harbor.

This popular fishing spot offers opportunities to catch a variety of fish, from striped bass to bluefish, while enjoying panoramic views of the harbor.

1. Explore the Halibut Point Reservation :

Extend your adventure beyond Halibut Point State Park and explore the adjacent Halibut Point Reservation. This scenic coastal area features walking trails that wind through wooded areas and granite quarries, offering unique perspectives of the rugged shoreline and the surrounding ocean.

FAQs about visiting Gloucester Massachusetts:

What’s the best time of year to visit.

Personally, I would always visit in the summer. There are just  so many things to do in Gloucester Massachusetts in the summer! However, each season has its perks.

Spring (March to May): Spring brings milder temperatures to Gloucester, with average highs ranging from the 50s to 60s Fahrenheit (10-20 degrees Celsius). This season is ideal for exploring outdoor attractions, such as hiking in Ravenswood Park or enjoying the blossoming scenery. Spring is also a great time to visit if you prefer fewer crowds and lower accommodation rates.

Summer (June to August): Summer is a popular time to visit Gloucester, thanks to its pleasant temperatures ranging from the 70s to 80s Fahrenheit (20-30 degrees Celsius). It’s the perfect season for enjoying Gloucester’s beautiful beaches, going on boat tours, and participating in outdoor activities like whale watching. Keep in mind that summer is also the peak tourist season, so expect larger crowds and higher accommodation rates.

Fall (September to November): Fall in Gloucester is a stunning season, as the foliage transforms into vibrant shades of red, orange, and yellow. Temperatures gradually cool down, ranging from the 50s to 70s Fahrenheit (10-20 degrees Celsius), making it comfortable for outdoor exploration. Fall is a great time to enjoy scenic drives, visit local farms for apple picking, and experience the autumnal charm of Gloucester.

Winter (December to February): Winter in Gloucester brings colder temperatures, with average highs ranging from the 30s to 40s Fahrenheit (0-10 degrees Celsius). While it may be chilly, winter can be a magical time to visit Gloucester, especially if you enjoy cozy indoor activities. You can explore museums, enjoy seafood by the fireplace in local restaurants, or witness the winter beauty of the coastal landscapes.

What Are The Best Hotels In Gloucester Massachusetts?

Gloucester, Massachusetts offers a variety of accommodations to suit different preferences and budgets. Here are some of the best hotels in Gloucester:

1. Beauport Hotel Gloucester : Located on the waterfront, Beauport Hotel offers luxurious accommodations with stunning views of the ocean . The hotel features elegant rooms, an on-site restaurant, a rooftop pool, and easy access to the beach. It’s a top choice for those seeking a high-end and picturesque stay.

2. Bass Rocks Ocean Inn : Situated on the rocky shores of Gloucester, Bass Rocks Ocean Inn offers comfortable rooms with ocean views . The inn features a private beach, a heated outdoor pool, and a continental breakfast. It’s an ideal option for a peaceful and scenic getaway.

3. Vista Motel : The Vista Motel is a budget-friendly option that provides clean and comfortable rooms. It’s conveniently located near Good Harbor Beach and offers easy access to downtown Gloucester. The motel is known for its friendly service and affordability.

4. Atlantis Oceanfront Inn : Overlooking the Atlantic Ocean, Atlantis Oceanfront Inn offers spacious rooms with balconies and ocean views . The hotel features a private beach, a heated outdoor pool, and a complimentary breakfast. It’s a popular choice for those seeking a relaxing beachfront experience.

5. Castle Manor Inn : Housed in a historic building, Castle Manor Inn offers charming accommodations with modern amenities . The inn features cozy rooms, beautiful gardens, and a complimentary breakfast. It’s located a short distance from downtown Gloucester and offers a tranquil atmosphere.

6. The Inn at Babson Court : Set in a restored 1870s Victorian mansion, The Inn at Babson Court offers elegant rooms and a warm, welcoming ambiance. The inn features a garden, a wraparound porch, and a complimentary breakfast. It’s a popular choice for its historic charm and attentive service.

7. Cape Ann’s Marina Resort : Located on the Annisquam River, Cape Ann’s Marina Resort offers comfortable accommodations with scenic water views. The resort features an outdoor pool, a marina, and waterfront dining options. It’s a great choice for those interested in boating and water activities.

What’s The Best Way To Get To Gloucester?

By Car: If you have access to a car, driving to Gloucester is a convenient option. The city is located approximately 40 miles north of Boston, and the journey takes about an hour depending on traffic. Major highways such as Route 128 and Route 1A provide direct routes to Gloucester.

By Train: The MBTA Commuter Rail offers a convenient train service from Boston’s North Station to Gloucester. The Newburyport/Rockport Line connects Boston with Gloucester, and the journey takes about an hour. Trains run regularly throughout the day, providing a comfortable and scenic way to reach Gloucester.

By Bus: Several bus companies operate routes to Gloucester from various locations. Greyhound and Peter Pan Bus Lines offer service to Gloucester from Boston’s South Station, as well as other nearby cities. Bus travel times and schedules may vary, so it’s advisable to check the specific routes and timetables in advance.

By Air: If you’re coming from a more distant location, flying to a nearby airport is an option. The nearest major airport is Boston Logan International Airport (BOS), located approximately 35 miles away from Gloucester. From the airport, you can rent a car or take public transportation to reach Gloucester.

By Boat: Gloucester is a popular destination for boaters. If you have access to a private boat or yacht, you can sail into Gloucester Harbor and dock at one of the marinas or yacht clubs. The Cape Ann Marina and Gloucester Harbormaster’s Office can provide information on docking facilities and services. You’ll definitely want to make a reservation ahead of time – boat spaces fill up fast in the summer months.

What Are The Best Towns Near Gloucester Massachusetts?

Rockport: Just a short drive from Gloucester, Rockport is known for its quaint New England charm. The town features narrow streets lined with colorful buildings, art galleries, and specialty shops. Bearskin Neck, a bustling pedestrian area filled with boutiques and seafood restaurants, is a must-visit spot. Rockport’s picturesque harbor, Motif No. 1 (a famous fishing shack), and stunning coastal landscapes make it a popular destination for visitors seeking a delightful coastal retreat. There are just too many things to do in Rockport!

Essex : Located along the Essex River, the town of Essex exudes a charming small-town atmosphere. It is renowned for its historic shipbuilding heritage and is home to the Essex Shipbuilding Museum. Visitors can explore the town center’s antique shops, art galleries, and local eateries. Don’t miss out on trying fresh seafood at one of the renowned restaurants specializing in clam shacks and seafood joints.

Salem: Salem is a historic and enchanting town known for its rich history, witch trials, and maritime heritage. Explore the charming streets of downtown Salem, lined with beautiful historic homes and unique shops. Visit the Salem Witch Museum or the House of the Seven Gables to learn about the town’s infamous past. Discover the picturesque Salem Harbor, where you can enjoy waterfront dining, take a harbor cruise, or simply soak in the scenic beauty. Salem also offers a vibrant arts and culture scene, with numerous museums, galleries, and seasonal events that attract visitors from all over. Check out some of our favorite things to do in Salem here.

Manchester-by-the-Sea : Situated along the North Shore of Massachusetts, Manchester-by-the-Sea is a quaint coastal town with elegant architecture and stunning ocean views. Stroll along the tree-lined streets, admire the beautiful homes, and explore the charming downtown area with its unique shops and cafes. The town’s picturesque Singing Beach, known for its squeaky sand, is a favorite spot for locals and visitors alike.

Ipswich : With its rich colonial history and scenic beauty, Ipswich offers a delightful mix of historical charm and natural landscapes. Explore the well-preserved historic homes along High Street, visit the renowned Crane Estate and its breathtaking gardens, or take a stroll along Crane Beach, one of the most stunning beaches in the region. Ipswich is also known for its local clam shacks, where you can savor freshly caught seafood.

Newburyport : Located at the mouth of the Merrimack River, Newburyport is a charming coastal town with a vibrant downtown area. Its brick-lined streets are filled with boutique shops, art galleries, and restaurants. Visitors can enjoy waterfront views at the picturesque boardwalk, explore the historic district with its Federal-style homes, or take a boat cruise along the river. There are plenty of things to do in Newburyport during every season.

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32 fun things to do in gloucester, massachusetts.

So, the warmer weather and longer days have you thinking about a coastal escape. We’re with you 100%. Whenever St. Patrick’s Day starts rolling around we start getting restless and start thinking of beaches, boating and consuming copious amounts of crustaceans.

If you’re thinking of heading up to Cape Ann for a little rest and relaxation this Summer or Winter/Fall for that matter, then this article is for you. Here are 32 fun things to do in Gloucester, Massachusetts.

1. Good Harbor Beach

So, we think a logical place to start a discussion about things to do in Gloucester, MA is to talk about its incredible beaches. Gloucester is home to some world class beaches that are truly some of the best in New England. One of our favorite Gloucester beaches is Good Harbor Beach.

With beautiful soft white sand, a large area to spread out, incredible views of the Thacher Island lighthouse , and the ability to walk out to Salt Island during low tide, Good Harbor is a fantastic spot to spend a Summer day.

In the off-season you can still enjoy the beach and even bring your dog out for a run to burn off some of that extra energy. To learn more about Good Harbor you can read our Definitive Guide To Good Harbor Beach

2. Take an Historic Sail

Take a step back in time and set sail out of Gloucester Harbor aboard the 65-foot Schooner Lannon. Get a feel for what life was like aboard this authentic fishing schooner. You can even book a private charter or have a wedding aboard the ship!

The striking schooner was built in 1997 in Essex, MA. Framed with local white oak and black locust, the schooner has a length on deck of 64.5 ft and overall length of 90 ft.

The Schooner Lannon offers a variety of food options as well as beer, wine and other drinks to enjoy during the sail. It’s a fantastic way to get a different look at Gloucester harbor.

3. Get Some Fresh Seafood From A Fishmonger

Gloucester is a working fishing port and home to some of the freshest seafood that you can buy. Whether you are looking for some fresh lobster, cod, tuna, or stuffed quahogs Gloucester has you covered! 

A few of our favorite local shops include:

Connolly Seafood: http://www.steveconnollyseafood.com/ Captain Joe & Sons Lobster: http://www.wholesalelobster.com/ Turners Seafood: https://www.turners-seafood.com/gloucester-market/

4. The Perfect Stop, For The Record

We miss record shops. The process of finding the perfect album or discovering a hidden gem and the tangible community experience. And, if you think we are the same people that still like actual books better than e-books, consider us guilty as charged.

If you’re looking to take a step back in time and find the perfect record or that CD that you used to love you have to take a trip over to Mystery Train Records .

Located right on Main Street in Gloucester, Mystery Train has a great selection of rare & collectible vinyl from just about any genre you can imagine. Heck, they even have eight track tapes!

If you’re up in Gloucester, it’s definitely worth a stop!

5. Shop at Independent Bookstores

Speaking of actual books, Gloucester has some incredible independent bookstores where you can peruse the stacks and find some incredible beach reading. A couple of stores that we love are Dogtown Books and The Bookstore of Gloucester

Dogtown Books offers a wide selection of preowned books, certified pre-owned books, and just general used books to choose from. They topics range from culinary adventures to space exploration and the owners are very friendly and welcoming.

The Bookstore of Gloucester on the other hand has been serving Cape Ann readers for over 45 years and offers the perfect local alternative to Amazon. It’s a great spot to pick up the latest releases and browse the curated collection.

If you are interested in Independent Bookstores take a closer look at our article on 5 Great Independent Bookstores on Cape Ann .

6. Step Back Into Medieval Times

If you are a fan of history and architecture, you have to make a point to stop at Gloucester’s Hammond Castle. Constructed by the eccentric inventor John Hays Hammond in the 1920’s, Hammond Castle serves as a beautiful showcase for Hammond’s impressive collection of Roman, Medieval, and Renaissance artifacts.

John Hays Hammond was a legendary inventor, holder of over 400 patents and is known as “The Father of Remote Control.” Visitors can tour the courtyard, great halls, secret passageways and war room and marvel at the beauty of the castle grounds.

In October, Hammond Castle even gets in the Halloween spirit with special haunted tours. If you fall in love with the castle you can even decide to host your wedding on site! It’s such a cool venue that it made our list of the Top 5 Gloucester MA Wedding Venues .

7. Rent Some Toys

We all know the common sayings about boats: “a hole in the water you throw money in” and “break out another thousand.” Of course there is some truth in the sayings, but enjoying Cape Ann on the water gives you a whole new appreciation for this incredible landscape.

Instead of buying a boat, paying for a slip, paying for fuel, registration, maintenance etc. why not just rent a boat? Well, at Gloucester Boat Rental you can do just that! They have a nice selection of boats from Key West, Striper, Sea Pro and Grady White that you can rent for 4 hour and 8 hour increments.

So grab a couple friends, a couple fishing poles, and something to sip on and hit the open ocean for the day.

8. If You Get Confused Listen To The Music Play

Covid has had us all itching to get back out and see some live music. A great local spot in Gloucester to catch music is Minglewood Harborside. Owned by the Serenitee Restaurant Group, they have a Jam Session every Monday night as well as other musical acts throughout the week.

Recently remodeled, Minglewood offers a large bar area adorned with some hearty nods to Jerry and the Boys. The menu at Minglewood truly has something for everyone from burgers and pizza to sushi and fresh seafood dishes.

So knock back a couple more shots of whiskey and head on down to Minglewood.

9. Visit Eastern Point Lighthouse

Cape Ann has no shortage of lighthouses and one of the best around has to be the Eastern Point lighthouse. This iconic lighthouse was originally built back in 1832 and reconstructed a couple of times.

The current 36 foot tower was built in 1890 and has an attached 2 story keepers quarters. Eastern Point You will see images of Eastern Point in publications about Gloucester and the lighthouse was even home to Winslow Homer back in 1880.

You can drive out to the light, park and take the half mile walk out on the dog bar breakwater to the Dog Bar Lighthouse. It’s a beautiful area and a great spot for a sunset or sunrise. If you want to see some incredible footage of the lighthouse you have to check out this Kenny Chesney video that was shot in Gloucester . 

10. Get Some Tasty Ice Cream

We love Ben & Jerry’s. They were the hearty pioneers that took it upon themselves to open an ice cream shop in Burlington, VT, of all places. But they had a vision and they paved the way for ice cream as we know it today.

Following in their footsteps is Holy Cow Café in Gloucester, MA. We think Holy Cow can best be described as Ben & Jerry’s meets Christina Tosi’s Milk Bar. One bite of this ice cream will have you invoking their name.

With cereal infused flavors like Gold Rush (Frosted Flakes steeped ice cream loaded with Golden Oreos!) and Cereal Milk (Fruity Pebble steeped ice cream mixed with colorful cereal marshmallows! Colored with all natural Blue Spirulina!) you are sure to be transported back to your 11 year old self.

Holy Cow also does exclusive flavor collaborations with local businesses such as the Taste The Rainbow collaboration with Gloucester’s Cafe Sicilia (pictured above). If you have a sweet tooth then you should definitely put Holy Cow Ice Cream on your list of things to do in Gloucester, MA. 

11. Head To The Theatre

The Gloucester Stage Company, founded in 1979, is an award-winning company that is a vital part of the fabric of Gloucester.

Since 1987, the Company has called East Gloucester home. Their performance center is housed in a former Gorton’s Fish Company Warehouse that Gorton’s kindly donated to the Company. It doesn’t get much more Gloucester than that!

The intimate but comfortable venue includes a refreshment bar and foyer and is a fantastic spot to catch a show. We’d recommend grabbing a bite at nearby Duckworth’s Bistrot before the performance.

12. A Whale Of A Time

One of the most popular activities on Cape Ann is whale watching and we would highly recommend it. Sign up with Seven Seas or Cape Ann Whale Watch and head out to marvel at these mammoth mammals.

The most common whales that you will find off the coast of Gloucester include the Humpback, Minke and Finback but you may also get a chance to see dolphins, sharks, and sperm whales.

On the three hour tour you will likely see the whales dive, breach, lay on their back and slap their fins and if you’re lucky you may even witness a bubble net! Learn more here: Gloucester Whale Watch Discount . 

13. Relax, They’ve Got Your Back

If you’re looking to relax and unwind, there’s no better medicine than a good massage. Gretchen and skillful team at Saltwater Massage in Gloucester are second to none and you can rest assured that you will come out of Saltwater feeling calmer and happier than when you arrived.

Whether you are looking for CBD Massage Therapy, Therapeutic and Deep Tissue Massage, Prenatal Massage, or you’re into hot stones and cupping, they have you covered.

14. When In Rome…Light One Up

So recreational marijuana is now fully legal in Massachusetts. You can now walk right into a dispensary and acquire the devil’s lettuce and a variety of other products that can heighten THC levels in your body.

Whether you prefer to smoke, vape, munch on edibles or drink an elixir, Happy Valley Dispensary in Gloucester has your cannabis needs covered.

Whether you are a regular user or are just looking for a flashback to the glory days, a stop at Happy Valley is sure to make your journey to Cape Ann a little more interesting.

15. Take A Sunset Dinner Cruise

Set sail aboard the Beauport and take a sunset cruise while enjoying a delicious seafood feast of lobster, corn, and clams. Enjoy the views of Gloucester Harbor including the downtown, Eastern Point, Rocky Neck, Stage Fort Park and Hammond Castle.

The boat comes equipped with a full bar so you can enjoy your beverage of choice. The cruise lasts a couple of hours and it’s a great way to cap off a beautiful day up in Gloucester, Massachusetts. In addition to dinner cruises, Beauport Cruiselines also offers lunch cruises, live jazz Sunday brunches and you can even book a deck or the entire boat for your wedding.

16. Acai Bowling 

Food trends come and go but acai bowls are forever. The acai bowl is essentially a healthy smoothie with tasty toppings that is the perfect way to start your day. Acai berries (annoying guy says that technically they are drupes) are a superfood that come from the rainforest that are loaded with antioxidants, boost brain function and lower cholesterol levels.

In Gloucester, you can get your acai on at Castaways Vintage Café . 

Castaways is an adorable café that offers acai, some delicious coffee beverages as well as vintage clothing. The vibe at Castaways is an island vibe that is mix between tiki hut and surf shop. When that Acai craving hits, Castaways is your destination. 

17. Revel In The Cut Bridge Carnage

The Blynman Bridge, also known as the “cut bridge” is a bridge that was built back in 1907 to honor Richard Blynman, the first minister and a prominent citizen of Gloucester. Blynman’s efforts were pivotal in digging the canal connecting the Annisquam with Gloucester Harbor.

Blynam’s cut through the isthmus took place in 1643. The bridge is now a popular spot for locals and tourists to loiter and watch the boats head in and out.

Some of the boats from Wicked Tuna dock at nearby Cape Ann Marina so you can sometimes catch celebrity boats like FV Tuna.

To get a taste of the carnage you can watch the Captains navigating the tight canal on the Cut Bridge Craziness Instagram page . It’s a fun take for a few laugh and some questionable navigation decisions.

18. Get Your Vitamin Sea at Wingaersheek

If you are itching for some beach time and some of that thick salt air it’s always a great plan to head over to Wingaersheek Beach. One of our favorite Gloucester beaches, Wingaersheek offers a beautiful beach that runs along Annisquam River and Ipswich Bay.

Known for its long sand bar at low tide, Wingaersheek is a great spot to spend a Summer day in Gloucester and that’s why it had to be on our list for the best things to do in Gloucester, MA. If you want to learn more about Wingaersheek, check out this Definitive Guide to Wingaersheek Beach .

19. Hop On A Foodie Tour

What better way to explore the coastal cuisine of Gloucester, Massachusetts than on a foodie tour! Try a little bit of everything and learn about some of Gloucester’s hidden gems on the Cape Ann Foodie Tour.

From thick and tasty claim chowder to homemade olive oil and delicious Italian sandwiches, Cape Ann Foodie tour will expose you to the culinary delights of the area.

Learn more about their schedule and some of the stops here – Cape Ann Foodie Tours

20. That’s What’s SUP

Want to get out on the water and try something a little different? How about stand up paddle? Cape Ann SUP has you covered. With locations at Pavillion Beach in Gloucester, Long Beach and on the Essex River.

Cape Ann SUP offers stand up paddle tours, surfboard rentals, and yoga classes.

The staff are all super friendly and knowledgeable and will provide you the necessary instruction so that you can get out there and have some fun on the water. We’re not saying you’ll become Kelly Slater by the end of the day, but we promise that you will have some fun and make some memories.

21. Scuttle Across The Rocks at Rafe’s

If you are looking for a short hike that takes little effort but offers a big reward, then Rafe’s Chasm is the hike for you! Located at 138 Hesperus Ave in the Magnolia neighborhood of Gloucester, Rafe’s Chasm provides a great cliff top view after a short flat hike through the woods.

Rafe’s Chasm has an interesting history death and shipwrecks and is a popular spot for adventurous divers.

Click here to l earn more about Rafe’s Chasm and it’s history .

22. Fishing For A Good Time

Embrace your inner angler with a trip out into the historic Atlantic on a deep-sea fishing charter. Set out on the same waters as Captain’s Courageous, and the Perfect Storm and try your hand at hauling in some stripers, cod, halibut, and haddock.

You can choose from a half day (4.5 hours), full day (9 hours), or a fishing marathon (12 hours). You will head out to the deeper waters and fish anywhere between 100 and 300 feet.

The Yankee Fleet offers 3 fantastic vessels to choose from: The Yankee Freedom, a 100 foot vessel that can accommodate 135 passengers, The Yankee Clipper, a 75 foot vessel that can accommodate 113 people and The Yankee Patriot II.

23. A Perfect Storm

After you get back from fishing, knock a few back at the Crow’s Nest. Featured in the blockbuster hit, The Perfect Storm, the Crow’s Nest is the perfect embodiment of Gloucester’s working waterfront.

The Crow’s Nest has offered Gloucester fisherman, locals and tourists drinks and accommodations for over 40 years. The walls are full of memorabilia from the movie and pictures of the actual crew from the Andrea Gail. It’s a local dive, but the folks are friendly and the drinks prices are fair.

You can check out some pictures from their gallery here: Crow’s Nest Gallery  

24. Rocky Neck Art Colony

One of the oldest continuously operating art colonies in the United States, Rocky Neck is a great place for a summer visit. Over the years, the unique landscape, beautiful light, and rich culture has drawn many artists to the shores of Gloucester. Some famous plein air artists include Winslow Homer, Edward Hopper, and Childe Hassam. The area was also frequented by writers Rudyard Kipling and Louisa May Alcott.

The art colony is still a vibrant community with a large membership , many of which still have studios on Rocky Neck.  It’s a beautiful place for a stroll and there are some great restaurants like The Studio and Duckworth’s Bistrot nearby should you need some sustenance.

25. Stay At A Local Inn

One of the great things about traveling to Cape Ann is that there really are not any chain hotels in the area. All the lodging properties are privately owned and offer a unique staying experience.

One popular lodging option for travelers to Gloucester is the Blue Shutters Inn . Located right off of the shores of Good Harbor Beach, Blue Shutters provides guests a comfortable and convenient location for their coastal escape.

Another option for Gloucester travelers is the stay at one of the historic inns in Rockport, Massachusetts. Rockport offers a great variety of inns including the stylish and charming, Addison Choate located right in the heart of the coastal village.

Regardless of where you choose to hang your hat, you are sure to be treated to hospitality that is second to none.

26. Outdoor Concert In The Park

Every year in August, Stage Fort Park in Gloucester turns into a mini-woodstock when the Riverfest Seaside Music Festival comes to town. The festival was cancelled in 2020 due to Covid, but in 2019 the festival featured Tall Heights, Mt Joy, Noah Kahan, and was headlined by good old Guster.

The best part is that the festival is open to the public, free of charge!

In addition to music, the festival also includes food trucks, a beer garden and other tasty refreshments to keep you cool on a hot summer day. If you need to cool off you can also walk right over to beautiful Half Moon Beach and jump on in!

27. St Peters Fiesta

A long-time Gloucester tradition, St. Peter’s Fiesta is a 5-day festival that honors St. Peter, the patron saint of fishermen. The annual festival takes place in late June every year and features parades of statues, boat races, masses and prayer.

The highlight of the event; however, is the weekend long Greasy Pole Competition. The Greasy Pole Competition traces its roots back to Sicily in the 1800’s and was brought to Gloucester by Italian immigrant fishermen.

The spectacle involves a 40ft piling that is raised up 30ft above Gloucester harbor, greased up with bacon fat, Crisco and fish guts to create a slippery surface, and contestants must then run to the end of the piling and grab flag.

Winners will treated to adulation, complimentary libations and memorialization on the St Peter’s Fiesta Wikipedia Page. You can check out the list of past Greasy Pole Winners Here . 

28. Visit Fisherman’s Memorial Monument

It’s no secret that Gloucester has a rich seafaring tradition. Home to one of America’s oldest fishing ports comes with its ups and downs. Over the years, the town has lost many mariners to the Atlantic and in 1925 the iconic man at the wheel was constructed to honor their legacy.

The eight-foot-tall bronze statue rests upon a five-foot base and is inscribed “They That Go Down To the Sea In Ships, 1623 – 1923. It’s a powerful reminder of the power of the ocean, human mortality and the brevity of our time. Being tossed at sea in a modern vessel can be nerve-wracking, it’s frightening to imagine being miles off shore in an old schooner.

The Fisherman’s Memorial is located right off Stacy Boulevard and if you are visiting Gloucester, it’s an absolute must stop.

29. Interior Design Mecca

Perched on a ledge overlooking Gloucester Harbor is the home of one of America’s first interior designers, Henry Davis Sleeper. Beauport, the Sleeper-McCann House, was Sleeper’s summer retreat and the 40 room mansion houses Sleeper’s diverse collection of folk art, pottery, antiques and other artifacts.

A National Historic Landmark, each room is distinguished by a historical or literary figure and no two rooms are the same. The property even features a beautiful garden and a secret staircase. The Sleeper McCann House is open from late May to Mid-October and is definitely one of the best things to do in Gloucester.

30. A Day At The Museum

Another great stop for visitors to Cape Ann and Gloucester is the Cape Ann Museum . The museum is a celebration of art, history, and culture of Cape Ann.

The museum features a fine art collection which boasts some fantastic marine art from artists such as Fitz Henry Lane as well as other talented painters and sculptors who called Gloucester home.

It is also home to the Fresnel Lens from Rockport’s Thacher Island that dates back to 1861. Designed by French physicist August-Jean Fresnel, the lens cast a beam for 22 miles keeping Cape Ann mariners safe for many years.

In addition to its permanent exhibits, the Cape Ann museum has a fantastic rotation of special exhibits and other programs and events throughout the year.

31. Trek Through The Dogtown Wilderness 

Dogtown Common provides hikers with an incredible 3,600 acres of mysterious woods, large boulders and carved stone to explore. Originally settled back in 1693, settlers chose the location due to its rocky inland landscape that offered protection from pirates and combative natives. The settlement was abandoned back in the early 19th century and has not been inhabited since. 

With some incredible trails, Dogtown offers a great opportunity for hiking, biking, running, cross country skiing and an outing with you furfriend. Along the paths you will find large boulders with sayings carved into them. These boulders were carved by unemployed Finnish quarrymen during the Great Depression who were commissioned by local entrepreneur Roger Babson.  There are 36 boulders that were carved with inspirational sayings such as “Never Try Never Win” and “When Work Stops Values Decay.” 

The name Dogtown is said to date back to the American Revolution and is derived from the dogs that the women kept while their husbands fought in the war. At one point it was estimated that there were anywhere from 60 to 80 homes in the area.  But after the war, the ports became safer, the fishing industry returned and so too did the settlers to the coastline. 

So if you’re in the mood for a journey off the beaten path, Dogtown is a great thing to do in Gloucester. Here is a link to a great Dogtown Guide . 

32. Get Your Omega 3 Fix 

While you are in one of America’s oldest fishing ports, you are probably going to consume some of that fresh bounty. Well, as you can imagine, there is no shortage of local restaurants serving up delicious seafood dishes.

If you are looking for a nice sit down meal with creative cuisine prepared by a talented chef, we would recommend Tonno , right on Main Street in Gloucester. If, one the other hand, you are thinking about getting a classic seafood platter with fried clams, haddock, shrimp and fries, then you should visit The Causeway . It’s a no-frills Gloucester institution that cranks out some really good eats.

Another excellent restaurant with a menu that runs the gambit from Sole Meuniere to Paella is Lobsta Land ! Located right of 128 it has old school fish shack vibes, a nice marsh view, and some tasty cuisine. There are many other great places to stop as well, but these are a few that we love. 

32 Things To Do In Gloucester 

Well, we hope that you enjoyed our 32 Suggestions! This is really just scratching the surface of all of the things that there are to do and explore on Cape Ann. If you enjoyed this article you may also enjoy our article about 40 fun things to do in Rockport, Massachusetts ! We hope that you enjoyed your trip up to Cape Ann, it’s truly a special place. 

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30+ Things To Do In Gloucester, MA

From dining on fresh seafood and wandering historic streets to relaxing on the beach or getting out on the water, there are endless things to do in Gloucester, MA. You’ll never run out of things to do in this North Shore town.

Once a small fishing town, Gloucester is now one of the largest towns on the North Shore. Located on Massachusett’s Cape Ann, Gloucester has direct access to Boston via the Commuter Rail and is home to some of the best beaches on the North Shore.

But there’s so much more to this Cape Ann town than the beaches (though you should definitely check them out).

Below are 30 of the best things to do in Gloucester, with something for everyone no matter your interests.

Table of Contents

The Best Things To Do In Gloucester

Go whale watching.

The area just off Massachusett’s coast is populated by some truly incredible marine life. So what better way to take advantage of Gloucester’s beautiful New England surroundings than by going on a whale watching trip?

Not only can you enjoy a scenic boat ride and have an opportunity to spot some wildlife along the way, but you’re also able to learn more about whales. There will be a naturalist on board with the captain and crew, and you will receive guided commentary to teach your group about the animals.

This journey will take approximately four hours, and you are guaranteed to have sightings of the whales!

You can also sign up for a similar four-hour whale watching experience here . Prices start at $48 per person!

Take a self-guided driving tour

If you’d rather stick to land, but still want to explore what the Cape Ann area has to offer, a driving tour might be just what you’re looking for! Plus, if you go the self-guided route, you’ll get to enjoy the comfort and privacy of your own vehicle without sacrificing the insights that can only come from a narrated tour.

You can learn a great deal of local history and explore the beautiful lighthouses and quaint villages that line this part of the shore. Plus, since you will not be beholden to a structured tour, you can go at your own pace and stop to explore anything that catches your eye.

This experience starts at $14.99. The best part is that you only need to pay per car, instead of per person, which makes this a very affordable activity for any group.

Explore on electric bikes

If you don’t have a car available, or you’d like to explore with the wind on your face and no guide in your ear, electric bikes are the perfect option. You can rent a bike for the day and feel connected to the scenery that surrounds you as you ride around Cape Ann.

Go wherever moves you, even if it is off the beaten path. E-bikes give you the freedom to discover more because they won’t tire you out the way that traditional bicycles can. You will only be restricted by the 8 hour time limit on the bike rental, but that gives you plenty of time to explore!

Rentals can be booked here , and they start at $61.54 a person. The bike can be dropped off at any hotel or home in the area!

Go to some of the best beaches on the North Shore

New England’s coastline is home to many beautiful beaches . In Gloucester, you’ll find that are some particularly stunning areas to enjoy the white sand and salty sea air.

Wingaersheek Beach is one of the best spots for a seaside stroll, though technically this beach is on the shore of the Annisquam River (which feeds into Ipswich Bay). There are tons of tidal pools to investigate, as well as sandbars, dunes, and rocks aplenty. Plus, there are lifeguards from 9-5, except during the off-season. There are also showers and bathrooms available.

If you’re in the area, you also won’t want to miss Good Harbor Beach. This is one of the region’s most popular destinations for surf and sand, for good reason. It’s incredibly scenic with stunning views of the sea, as well as the twin lighthouses that can be found on Thacher Island. There are also lifeguards in the summer here, as well as bathrooms and showers year-round.

Just a short way over in Rockport, you can find another incredible beach. Long Beach doesn’t have the same amenities as the Gloucester beaches, but this quant beach-house-lined stretch of sea and sand makes up for it with stunning views of the twin lights on Thacher Island.

Buy fresh seafood from a fishmonger

If you love lobster, crab, or fish, you might just mistake Gloucester for heaven. That’s because this little Massachusetts town is an active fishing port. In fact, Gloucester is the oldest fishing port in the country.

This means that you won’t be able to find seafood fresher anywhere else! So it would be a crime to visit Cape Ann and not taste the local fare, especially since eating out is one of the best parts of traveling.

A few local favorite fish mongers include Turner’s Seafood Market, The Fresh Lobster Company, and Connolly Seafood. However, you’re sure to find plenty of other options if you just explore!

Shop at independent bookstores

When you’re on vacation, especially at the beach, it can be nice to dig into a good book. There’s nothing more relaxing than setting up a towel or chair on the sand and getting lost in a story. So if you’re in the market for a good book while you’re in Gloucester, why not shop small and support a local bookshop?

Even if you’re not a reader, you can still appreciate that Dogtown Books is one of the coolest stores in town. This shop specializes in “used and unusual” books and has been providing Gloucester with books since 1997. They also frequently host book clubs, open-mic nights, author events, and readings, so it’s worthing checking their schedule for the dates that you’ll be around!

Another great option is The Bookstore of Gloucester . This historic shop has been operating since 1974, and offers an incredible and curated selection of stories. If you’re looking for a great read, they have you covered.

Wander the Hammond Castle Museum

If you’re looking for something truly unique, the Hammond Castle Museum offers a really special experience. After all, how many European Castles can you find in the American Northeast?

The museum is a great place to learn about the life and creations of the inventor, John Hays Hammond Jr. He was a bright man who is most known for his work on radio control and there are numerous exhibits that cover his contributions to technology.

However, the real draw of this museum is the stunning architecture that can transport you in time. In the 20s, Hammon commissioned a residence to be built on a bluff that looks out onto the Atlantic Ocean. His goal was to recreate a Medieval Castle for himself.

The building’s stunning architecture features design components from every century from the 1400s on, and it’s truly a sight to behold. Hammond was inspired by his love of history, and this also drove him to amass a huge collection of artifacts from the Renaissance, Middle Ages, and earlier periods as well. Many of these are on display at the Hammond Castle Museum, so it can be a beautiful place to learn about art and times that have passed, as well.

Tickets can be purchased on the museum website . They are $20 for those 12+, $15 for senior citizens, and $10 for children between 5-12. Kids under 5 can get in for free!

Rent a boat

If you’re looking to explore Cape Ann, don’t feel limited to land! There are tons of opportunities to get out on the water and enjoy the ocean. And if you’re over 21 and have a driver’s license, renting a boat can be one of the most amazing ways to experience the sea.

Gloucester Boat Rental offers a variety of different boats that can be taken out by groups with up to 8 passengers. The boats can be rented for a full or a half day, and you’ll be able to assume the Captain’s role and tour the area however you would like to.

Prices vary depending on the boat you select, but you can learn more about the options here . For a full-day, an inflatable boat can be rented for as little as $500!

If you’re in New England for the seafood, what better way to enjoy fresh fish than to catch it yourself? Plus, fishing isn’t just rewarding for your stomach, it’s a really fun and relaxing way to pass the time and enjoy the water.

Yankee Fleet Deep Sea Fishing has been offering fishing excursions since 1944, so there is no company more seasoned and qualified to take you out on the sea. Plus since there is a captain and full crew on board, you won’t need to worry about anything besides your catch.

There are many different packages available for different trip lengths. However, half days start at $50 a person for 4.5 hours, and a full 9 hour trip is $74. There are also longer excursions available, including overnights.

Sail on the Schooner Thomas E. Lannon

Since Gloucester is America’s oldest fishing port, it’s a town steeped in history. It can be fascinating to take a step back in time and learn about what life was like for previous generations. One particularly fun way to explore the local history is to charter the Schooner Thomas E. Lannon.

Taking a ride on this sailboat will allow you to simulate the experience of fishermen in the early 1900s. Plus, it’s just a beautiful way to get out on the water. The Thomas E. Lannon can hold up to 49 passengers. This vessel also comes equipped with snacks and a bar so that you can have a perfect time aboard.

Public sails last around 2 hours and start at $48 for adults. There are also sunset cruises and private charters available too. You can find more info here .

Visit the Eastern Point Lighthouse

The lighthouses that decorate the New England coastline are a sight to behold. These charming structures draw in tons of tourists, as they are found in scenic surroundings and offer a fascinating window into the past.

The Eastern Point Lighthouse in Gloucester is one of the top attractions in the area, so if you’re in Cape Ann, it’s worth checking it out. This lighthouse was first built in 1832 and makes for a beautiful photography subject.

Unfortunately, as the lighthouse is now operated by the United States Coast Guard, it is not currently open to the public. However, it is still worth exploring the area so you can get a glimpse of it, even if you can’t go inside.

Indulge your sweet tooth at Holy Cow Ice Cream

If you get a hankering for something sweet while you’re exploring Gloucester, you’ll definitely want to stop into the Holy Cow Ice Cream Cafe . It’s a fun little joint with a great atmosphere and even better desserts.

Holy Cow offers really high-quality ice cream that is entirely homemade. On top of that, they have an eclectic menu that includes some really fun and exciting gourmet flavors. Cinnamon Churro Dough, Pineapple Upside Down Cake, and Cold Brew Oreo are just a few of the delicious flavors that you may not find elsewhere. If you want something really special, their ice cream sandwiches can’t be beaten either.

Holy Cow is also great if you are vegan, lactose-intolerant, or traveling with someone with one of these dietary restrictions. They have a separate menu that is entirely vegan and dairy-free, so everyone can enjoy a cone!

See a performance at the Gloucester Stage Company

For some culture and a chance to support the local arts, look no further than the Gloucester Stage Company. This professional theater company is also a non-profit that works to enrich the local community with engaging performances throughout the year.

Past performances have included classic shows like Spring Awakening and Shakespeare’s Hamlet. However, the Gloucester Stage Company makes a point to put on productions that are lesser-known as well. Furthermore, they are committed to diversity in their programming and take representation to heart when selecting a piece to perform and when they are casting.

Tickets start at $54 for adults, but package deals are available if you want to attend every play in a season.

Sunset cruise dinner (Beauport Cruiselines)

When you’re in a town known for its fishing, what could be more fitting than to indulge in some seafood on the water? A dinner cruise is a wonderful way to experience the sea. You’ll be able to really feel luxurious as you drink and dine on lobster while aboard a beautiful ship.

Beauport Cruiselines offers numerous fun trips, but the Sunset Dinner Cruise might be the most exciting. You’ll enjoy a New England Lobster Bake Dinner and be able to appreciate a full bar, live entertainment, and of course, the ocean.

Tickets start at $69 per person. There are also lunch cruises and special events that are available as well.

Stop by the “Cut Bridge”

Blynman Bridge is referred to almost exclusively as the “Cut Bridge” by the locals of Cape Ann. This little drawbridge is one of the most active on America’s eastern shore. In fact, some days, it is raised as many as 60 times.

It goes across the Blynman Canal, which is the connector between Gloucester Harbor and the Annisquam River. The Canal dates back to 1643, but the bridge was not constructed until 1907. There’s a lot of local history wrapped up in this little waterway, which is part of why a visit to the Cut Bridge can be so nice.

The Cut Bridge is also just a lovely sight for bridge enthusiasts or anyone looking to take in some of the quaint charm of New England. If you’re in the area, it’s definitely worth just taking a stroll by and snapping some photos of the bridge.

Go on a food tour

There are a lot of great things about traveling. There are new sights, cultures, history, and people to explore, which can be really exciting. However, without a doubt, one of the most enticing parts of going somewhere new is trying the local food.

New England is home to some phenomenal seafood, as well as many other great cuisines. In fact, there’s such an abundance of good food that you might not know where to begin. That’s the beauty of a food tour: a seasoned guide will take you to the best spots and let you sample a little bit of everything.

The Gloucester Food Tour from Cape Ann Foodie Tours will lead you to five to six different spots. You’ll be able to taste a classic chowder, some authentic cannolis, and many other delicious dishes. The tour is $59 per person, which covers all of the food. However, this does not include gratuity.

Go paddleboarding

Want an active way to enjoy your vacation and get out on the water? Paddleboarding can be just what you’re looking for. Stand-up paddleboarding can be a great workout, and it’s also a lot of fun. It’s the perfect activity for anyone looking for a little adventure while they’re in Gloucester!

Cape Ann SUP + Surf offers tons of different paddleboarding options that can accommodate all skill levels. If you’ve never tried it before, there are group or private lessons that you can sign up for. If you know the basics but would prefer a guided experience, you can also go on a paddleboard tour. There are also SUP Yoga classes and paddleboard rentals available if you’re ready for something more advanced.

Group lessons are $45 per person, and tours are $65 for each person. If you’re interested in renting a board and going off on your own, it’s $60 for 4 hours or $80 for a full day.

Attend a festival or special event

Depending on when you’re in town, there may be some exciting events happening. This is especially true in the summer when there is almost always something going on in Gloucester. Taking advantage of the local happenings can be a great way to have a unique experience and make some really special memories.

If your dates line up, the Riverfest Seaside Music Festival is one event that you won’t want to miss. There is always a great roster of live music to be found at this festival, plus lots of food trucks, entertainment for the kids, and plenty of booze for the adults.

If you’re able to, you should also check out St. Peter’s Fiesta. This is a five-day festival that happens every year in Gloucester to celebrate St. Peter, who is known to be the patron saint of fishermen. It’s one of the most exciting events in the Cape Ann area, and it brings in visitors from all over. There will be boat races, a carnival, a greasy pole contest, and much more!

Go to the Fisherman’s Memorial Monument & Fisherman’s Wives Memorial

As you may have gathered, Gloucester is a city that is pretty big on fishing. It’s America’s oldest fishing port, and the local economy still actively relies on this industry.

However, fishing can be a lonely and hard profession since much of the fisherman’s life is spent on the water, away from land, creature comforts, and his family. It can also be a dangerous career path, especially in the deep sea.

The Fisherman’s Memorial Monument seeks to honor and thank all of the fishermen who have sacrificed for their community. This statue commemorates the significance of this industry to Gloucester, and acknowledges the men who have sustained it.

But the burdens of the fishing industry don’t rest on the fishermen alone. They are also leaving behind wives who have to carry on in their absence. This can be a difficult burden to bear, especially when there are children. That’s why the Fisherman’s Wives Memorial honors the women behind the fishermen.

Spend an afternoon at the Cape Ann Museum

The Cape Ann Museum showcases the art and history of the region in a historic building that has become a shining beacon for the community. 

The museum was established in 1875 as the Cape Ann Scientific and Literary Association, but it has since evolved into a thriving cultural hub. The main site is located in downtown Gloucester. It has an auditorium, Library & Archives, children’s activity center, two sculpture gardens, a captain’s home from the 19th century, and various galleries housing both permanent and temporary exhibits. The Cape Ann Museum Green was inaugurated in 2020 as the new location of the Museum. Three historic buildings, open green space, and a brand new, state-of-the-art Collections Center can all be found at 13 Poplar Street in Gloucester, where CAM Green is housed. The Collections Center also has more space for displaying and storing CAM’s collections.

Get Spooky in Dogtown Common

Part of the Essex National Heritage Area, Dogtown Common is a legit ghost town. Its history is both strange and exciting. This area has rumors of suspicious drifters, wolves, witches, werewolves, curses, and scary dolls. 

Settlers first arrived in the region in 1693, drawn there by the relative safety afforded by the area’s interior location from both pirates and the native peoples, who were naturally displeased by the influx of strangers. Approximately one hundred households called Dogtown home during its heyday (1750-1800).

Dogtown, formerly known as the Common Settlement, received its name from the free-roaming pack of strays often seen in the area. Many women who had lost husbands at sea or in battle kept dogs for self-defense and company. These animals grew wild when their owners died and now roam the adjacent grasslands.

During the Great Depression, Roger Babson, founder of Babson College, hired unemployed stonecutters in Dogtown to carve uplifting messages on boulders and stones left behind by the glaciers melting. 36 of these mysterious and oftentimes unnerving writings are strewn throughout the landscape.

Dogtown in Massachusetts is now a rocky 3,000-acre park where tourists may explore the trails and tangled trees that once covered the town and discover the village’s abandoned cellar holes. However, many visitors have complained that the region is difficult to navigate due to its hazardous terrain and crumbling ancient farmstead foundations. The curious traveler hankering for a ghost town experience must visit Dogtown – with caution.

Stage Fort Park 

When the first immigrants arrived in Gloucester in 1623, they established fishing stages in this area. Half Moon and Cressy beaches may be found at Stage Fort Park , along with a sand volleyball court, a brand new playground, a baseball field, a basketball court, and tennis courts. There are public facilities, a visitor center with maps and information, a privately operated restaurant serving food, and many picnic tables and grilling sites (bring your own grill). There are various festivals, farmer’s markets, fireworks displays, concerts, and storytimes for kids throughout the summer. 

Ravenswood Park 

The environmentalist ideals of the park’s creator are reflected in Ravenswood Park’s 600 acres of calm space for reflection. Businessman and philanthropist Samuel Sawyer of the nineteenth century bought more than twenty-six parcels of land near his home on Freshwater Cove, including woods, pastures, and a swamp. Upon his death, Sawyer bequeathed this land to be developed into a park, which would be called Ravenswood, after the castle in Sir Walter Scott’s The Bride of Lammermoor. Snow-covered hemlocks, the fresh scent of spring, and relief from the sweltering heat of summer all await you here.

Rafe’s Chasm

The Trustees of the Reservation sold Rafe’s Chasm Park , a 10-acre space, to the City of Gloucester for a dollar in 1959. 

Views of Norman’s Woe rock to the northeast and Kettle Island to the southwest may be enjoyed from this beachfront park that stretches from Hesperus Avenue to the rock.

About fifty yards away from Rafe’s Chasm Park is private property where the chasm itself may be found. Please respect any signs that read “Private Property.”

This massive rock fissure, once known as Rafe’s Crack, was renamed Rafe’s Chasm on maps in the 1850s.

Legend has it that a formerly enslaved man called Ralph resided in the area around the Chasm and constructed many of the rock walls that can still be seen today along Hesperus Avenue, thus the name.

After the end of the Civil War, the chasm was discovered and quickly became a major tourist attraction.

Visit Beauport, the Sleeper-McCann House

Sleeper-McCann House in Beauport is a National Historic Landmark because it was the vacation home of Henry Davis Sleeper, one of the first professional interior designers in the United States. Beauport, which Sleeper built on a rock outcrop overlooking Gloucester Harbor, served as his haven, stage for social gatherings, and professional display.

The McCanns bought Beauport after Sleeper’s death and substantially preserved it. Travel to Beauport to explore every nook and cranny of Sleeper’s lifelong collection of oddities, colorful glass, folk art, ceramics, and silhouettes. There are forty unique rooms, each with its own theme, color scheme, decorative accent, or literary or historical character. In this hotel, there is no room that is like any other, and all of them are absolutely stunning. Meet Sleeper, a gay man who lived in the early 20th century, his housekeeper Mary Wonson, his interesting neighbors, and the house’s numerous eccentric visitors.

Visit the Cape Pond Ice Company

In 1848, blacksmith Nathaniel R. Webster founded Cape Pond Ice Company, then known as Gloucester Co., in response to the growing need for a consistent supply of ice by the fresh fish business. Fish, especially halibut and cod, were preserved in salt and brine prior to then.

Webster’s first ice house was constructed by damming a nearby creek.

Within four years, Webster constructed ice houses on Upper and Lower Day’s Ponds, near Foster’s Serv Station, and on Cape Pond in Rockport; the latter is now the company’s primary location.

In 1858, Webster’s son succeeded to the family’s ice monopoly in Cape Ann. 

These days, The business is available for commercial appointments at any time of day or night, all year round. In addition to filling tractor trailers and trucks with block ice or blown crushed ice, Cape Pond Ice can pump at a rate of one ton per minute on up to three fishing boats simultaneously. Pallets of bagged ice ranging in weight from 30 to 40 pounds are transported all throughout Cape Ann and New England.

The business caters to a wide variety of customers, including commercial fishing boats and processors, broccoli and poultry growers, redi-mix concrete builders, and customers who want unique ice sculptures. 

A viewing window in the office looks out on the 150-ton-per-day ice block manufacturing area. Tours of the facility are no longer available, but visitors may hear a free history talk in the gift shop, watch historic video footage, or take a peek at the wharf. 

Explore downtown Gloucester

Gloucester, Massachusetts, is the oldest continuously operating seaport in the United States and is known for its nautical heritage, delicious seafood, bustling waterfront, and stunning beaches. Experience the finest of New England’s coastal natural splendor while on land and marine activities. Downtown Gloucester has award-winning restaurants, chic stores, fun events, and a lively arts and culture scene.

Small Business Saturday, November 26, marked the beginning of the third annual Winter Lights on Cape Ann celebration, which continues until New Year’s Day, January 1.

Businesses in Essex, Gloucester, Ipswich, Manchester-by-the-Sea, and Rockport are joining up this year to decorate their establishments with more than one hundred holiday lights displays. Lights and elaborate window decorations are being set up in stores as a way for owners to get into the Christmas mood.

Rocky Neck Art Colony & Cultural Center

One of the earliest art colonies in the US may be found at Rocky Neck. Rocky Neck, a small peninsula in Gloucester’s working harbor, is well-known for its scenic beauty, its distinctive light, its rich cultural past, and its lively, supportive community.

Some of the most influential figures in American art history, such as Winslow Homer, Edward Hopper, Frank Duveneck, and Childe Hassam, were among the Plein air painters who called Rocky Neck home in the late 19th and early 20th centuries.

Many other modernists, such as Stuart Davis, Milton Avery, Adolph Gottlieb, Nell Blaine, and Mark Rothko, were also drawn to Cape Ann by its picturesque scenery and active waterfront.

Rocky Neck galleries host the works of dozens of local artists every summer, from painters and potters to textile designers, photographers, and even jewelry makers.

There is a wide selection of dining options to suit every palate, and on the weekends, many establishments provide live music to enhance the atmosphere further.

The Rocky Neck Art Colony, located in Gloucester’s Rocky Neck Cultural District, is a terrific area to take a walk on a sunny summer day, stop by on the way to or from the beach, or have a delicious dinner.

Visit Rockport 

A nearby town to Gloucester, Rockport is striking in its seaside beauty. Rockport played the role of a small Alaska village in the 2009 film The Proposal, starring Sandra Bullock, Ryan Reynolds, and Betty White.

I recommend watching the movie the night before you head to Rockport! It’s fun pointing out all the locations, from Motif No. 1 to the Fudgery and noticing the CGI mountains in the background.

There are a few things everyone visiting Rockport must do — explore Bearskin Neck, enjoy a lobster roll, and explore Halibut Point State Park.

You can grab a lobster roll at several locations, but I recommend Roy Moore Lobster Company and The Lobster Pool.

Roy Moore is in Bearskin Neck, so you can grab a lobster roll and take a short walk on the long beach there, hitting Motif No. 1 and checking out the other sites.

There are also breweries, beaches, art galleries, and much more. Check out my post all about Rockport here.

Visit Essex 

Essex is next door to Gloucester and is great for antiquing and seafood. It is known as the “Restaurant Capital of New England” due to the high concentration of eateries per resident.

Many of its traditional and innovative dining establishments are situated on the riverbanks of the Essex, with picturesque views of the estuary and Great Marsh. 

Essex is a great year-round destination for foodies because of its abundance of restaurants serving anything from freshly caught seafood to classic New England specialties with a creative twist. 

Sit back with a craft beer or beverage and watch the boats go by while you soak up some sun on an outdoor deck. When the weather outside is chilly, you may warm yourself by dining next to a fire.

Gloucester is jam-packed with rich cultural and historical sites, delicious food, beautiful art, and stunning scenery. When will you visit?

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Top 21 Best Things to Do in Gloucester Massachusetts

Our travel recommendations are based on personal experiences and research.

You’ll find plenty of things to do in Gloucester MA, including exploring the city’s maritime history, visiting a museum built to look like a castle, and soaking in nature on land and the water.

Nestled along the Massachusetts coast on Cape Ann, Gloucester beckons with a captivating blend of maritime charm and historical allure. At its core lies its historic harbor, thriving since 1616 and considered America’s oldest seaport.

With just over 30,000 people, Gloucester is much larger than its small-town peers. You’ll notice a bit of a city feel here as you stroll through the downtown, explore its shops and restaurants, and wander along the harbor-side promenade.

But with bigness comes cultural treasures, and Gloucester has many that dig into its seafaring roots. It’s impossible to leave Gloucester without a better sense of the risks and challenges faced in the open ocean and the sacrifices made at sea to make a living.

Beyond the harbor, Gloucester unfolds cultural treasures and scenic wonders. You can explore a museum resembling a castle perched dramatically overlooking the harbor. Or take a scenic drive that reveals coastal vistas, sandy shores, and expansive ocean views.

The best things to do in Gloucester MA

The following are 21 of the absolute best things to do when visiting Gloucester, Massachusetts.

Explore historic Gloucester Harbor

A focal point of Gloucester MA is its long stretch of harbor. Steeped in maritime history, the harbor is a living testament to Gloucester’s seafaring heritage.

Throughout the city, you’ll find multiple places that provide glimpses of the harbor, but one of the more popular areas is Stacy Esplanade, adjacent to Western Avenue (pictured above).

As you wander along the Stacy Esplanade you’ll come across the Gloucester’s Fisherman’s Memorial , an iconic symbol in the city that memorializes the many Gloucester fishermen lost at sea. The statue reads: “The That Go Down to the Sea in Ships. 1623 – 1923”.

Discover the Hammond Castle Museum

One of the more unique things to do in Gloucester MA is to visit the Hammond Castle Museum , a medieval-style structure overlooking Gloucester Harbor.

Built by inventor John Hays Hammond Jr., the castle features an impressive collection of artifacts, including medieval armor, artwork, and antique furnishings.

Explore the castle’s unique architecture and picturesque grounds for a captivating glimpse into Gloucester’s architectural and cultural history.

The museum’s available days and times fluctuate. Check the website for up-to-date details.

Take a scenic drive along the coast

Taking in coastal views is one of the best things to do in Gloucester MA, and driving is a great way to explore this scenic section of Cape Ann.

Starting at Hammond Castle, follow Route 127 north through downtown Gloucester toward Rockport. Along the way, you’ll be able to take in views of Stage Fort Park and Gloucester Harbor.

As you drive down Main Street, keep your eyes open for a right-hand turn onto Route 127A. This route continues closer to the coast, passing by Good Harbor Beach and Long Beach with views of the ocean in the distance.

Eventually, you’ll arrive in Rockport, a popular small town teeming with art galleries, stores, and its own beautiful coastal views.

Experience Good Harbor Beach

A popular thing to do in Gloucester MA in the summer is to relax and unwind at Good Harbor Beach, one of Gloucester’s most beloved sandy shores.

Visitors can bask in the sun, swim in the Atlantic Ocean, or simply enjoy a beachcombing stroll. The beach’s pristine beauty and family-friendly atmosphere make it a popular destination for locals and visitors alike.

Climb the Annisquam Lighthouse

Lighthouse lovers will want to carve out time in their itinerary for visiting the Annisquam Lighthouse , perched on the scenic Annisquam River.

The lighthouse’s location makes it the perfect spot to take in views of the surrounding harbor.

While the lighthouse isn’t open to the public, it is possible to wander around the exterior. Beware that parking is limited.

Discover maritime history at the Gloucester Maritime Heritage Center

Anyone interested in learning more about Gloucester’s seafaring legacy will want to visit the Gloucester Maritime Heritage Center .

Housed in an old icehouse, the museum provides a captivating journey into the town’s maritime history through exhibits, interactive displays, and an aquarium. You’ll learn about the lives of Gloucester’s fishermen, their challenges, and the enduring spirit that defines a coastal community.

Outside you’ll also find the Harriet Webster Pier, the oldest operating marine railway in the country, and have the opportunity to sail on the Schooner Ardelle .

Hours are generally Thursday through Monday from 10 AM – 4 PM. Admission is $12 for adults with special pricing for qualified individuals.

Go on a whale watching excursion

One of the most popular things to do in Gloucester MA is to experience a whale-watching cruise. The city features the closest port to two major feeding grounds for whales off the Massachusetts coast – making it an ideal locale for viewing these majestic creatures.

Onboard one of these cruises, you’ll have the chance to witness whales breaching against the backdrop of the open sea, creating unforgettable memories. Knowledgeable guides enhance the experience with insights into the marine life that inhabits the waters off Gloucester’s coast.

Cruises typically last about 3-4 hours and prices tend to be between $50-$100 a person.

Here are a few of the more popular cruise lines operating out of Gloucester Harbor:

• Cape Ann Whale Watch
• 7 Seas Whale Watch
• Windfish Private Tours and Fishing Charters

Stroll through Stage Fort Park

Outdoor enthusiasts will want to make time to visit the lovely Stage Fort Park , nestled against the coast with panoramic views of Gloucester Harbor and the Ten Pound Island Lighthouse.

The park features scenic walking trails, a long boardwalk along the water, lush green spaces, a playground, and picnic areas. And the park’s historical centerpiece, the Stage Fort, provides a glimpse into the colonial past of the region.

If you’re visiting Gloucester in the summertime, be sure to check the calendar for outdoor concerts, festivals, farmer’s markets or storytelling events for children.

Visit the Cape Ann Museum

Cape Ann, the peninsula that includes Gloucester and Rockport Massachusetts, has a rich and fascinating history that includes seafaring explorers and legendary artists.

A stop at the Cape Ann Museum tells these rich and interesting stories with its diverse collection of art and artifacts. You’ll also be able to explore exhibits that showcase the region’s maritime heritage and famed art colonies and view the works of local artists.

Two locations comprise the Cape Ann Museum. The downtown campus includes numerous exhibit spaces to explore. Admission is $15 for adults. ( 27 Pleasant Street ) The museum also has a newly acquired space called Cape Ann Museum Green – an outdoor space with three historic structures. ( 13 Popular Street )

Dine at Waterfront Restaurants

The spirit of Gloucester is bound with the sea, so it’s only natural you’ll want to enjoy a meal at one of the city’s waterfront restaurants.

Grab a meal of fresh seafood and other culinary delights with the scent of the salty sea breeze as your dining companion. From lobster rolls to clam chowder, the local eateries along the waterfront offer a feast for seafood enthusiasts. Each of these restaurants combines savory sensations with seaside scenic views.

• Minglewood Harborside – This restaurant offers modern American cuisine, focusing on fresh seafood. Its location on Rogers Street provides waterfront views.
• The Gloucester House – Overlooking the harbor, The Gloucester House is known for its seafood and New England specialties. It provides a classic waterfront dining experience.
• Seaport Grille – Situated at Cruiseport Gloucester, Seaport Grille offers waterfront dining and a menu featuring locally sourced seafood and other regional dishes.
• Beauport Hotel’s 1606 Restaurant & Bar – Located at the Beauport Hotel, 1606 Restaurant & Bar provides beautiful views of Gloucester Harbor and a diverse menu.

Shop local at Gloucester’s boutiques

While Gloucester may not have the quaint appeal of neighboring Rockport, you’ll still find your fair share of artisan boutiques, showcasing a variety of locally crafted treasures.

From handmade jewelry to unique artwork, these boutiques offer a shopping experience that reflects the creativity and craftsmanship of the local community.

• The Brass Monkey – Situated at 85 Main St, The Brass Monkey offers a curated selection of artisan gifts, jewelry, home décor, and accessories.
• Pop Gallery : Located at 67 Main St, Pop Gallery showcases contemporary art, jewelry, and unique gifts from local and international artists.
• Pauline’s Gifts : Found at 512 Essex Ave, Pauline’s Gifts is known for its collection of handmade and locally crafted items, including jewelry, home décor, and accessories.

Visit Rocky Neck Art Colony

Art lovers will want to immerse in the vibrant arts scene at the Rocky Neck Art Colony . Stroll through charming galleries and studios, where local artists showcase their talents against the picturesque backdrop of Gloucester’s rocky coastline. The colony’s creative energy and diverse artworks make it a must-visit destination for art aficionados and those seeking inspiration from the scenic surroundings.

Rocky Neck is a peninsula that juts into Gloucester’s harbor. You can access it by driving south on East Main Street and turning right on Rocky Neck Avenue. These are a few of the destinations you’ll find on Rocky Neck:

• Cape Ann Artisans Gallery – this gallery features a variety of works by local artists, including paintings, sculptures, jewelry, and more. ( 25 Lexington Avenue )
• The Cultural Center at Rocky Neck : This center, located at 6 Wonson Street, hosts galleries and studios where you can find a range of artworks, including paintings, ceramics, and crafts created by local artists. ( 6 Wonson Street )

Visit the Eastern Point Lighthouse

To fully bask in the seafaring history of Gloucester, visit the city’s Eastern Point Lighthouse . Built in 1832, a stop here allows you to take in maritime views and listen to the rhythmic crashing of waves as you explore the area surrounding this historic light.

A fun thing to do when visiting Eastern Point is to navigate the oceanfront path to the Dog Bar Breakwater. Walking down this narrow strip not only provides a different perspective of the lighthouse but also provides fantastic views of the harbor and sea.

From a distance, you can take in the full glory of the lighthouse, and admire the Gothic Revival keeper’s dwelling. Artist Winslow Homer lived here in 1880 along with Lighthouse Keeper, Charles Friend, and painted seascapes and the everyday life of the harbor.

Explore the Essex Shipbuilding Museum

One fun thing to do in Gloucester MA is to delve into the shipbuilding heritage of the city at the Essex Shipbuilding Museum .

Learn about the town’s role in the shipbuilding industry through exhibits, artifacts, and captivating stories. The museum provides a fascinating insight into the craftsmanship and maritime history that shaped Gloucester’s identity, making it a compelling destination for those interested in the town’s seafaring legacy. ( 66 Main Street )

Attend a Gloucester Stage Company Production

Immerse yourself in the world of theater by attending a production at the Gloucester Stage Company .

This local theater company, known for its intimate and engaging performances, showcases a diverse range of theatrical works. From thought-provoking dramas to lighthearted comedies, the Gloucester Stage Company contributes to the town’s vibrant cultural scene. ( 267 East Main Street )

Explore Dogtown Common

Hiking through the enchanting landscapes of Dogtown Common , an ancient settlement turned wooded wilderness, is among the best outdoorsy things to do in Gloucester MA.

Discover the mysterious boulders, cellar holes, and scenic trails that wind through this historic area. Dogtown Common offers a peaceful retreat for nature enthusiasts, providing a connection to Gloucester’s past while surrounded by serene natural beauty.

Dogtown  is an area in central Gloucester of about five square miles, or 3600 acres, stretching from the Riverdale section of the city, north of Route 128, into Rockport, and including the Goose Cove and the Babson Reservoirs.

Kayak or Paddleboard on the Annisquam River

Another way to experience Gloucester’s waters is by kayaking or paddleboarding along the Annisquam River.

This tidal, salt-water estuary, begins at Gloucester’s harbor and continues to the Annisquam Harbor in the north, dividing Cape Ann in two. As you paddle along the river, you’ll pass by lush landscapes and waterfront homes.

Whether you’re a seasoned paddler or a novice, the Annisquam River provides an idyllic setting for a peaceful and picturesque aquatic adventure.

Attend the Gloucester Schooner Festival

Celebrate Gloucester’s maritime heritage by attending the annual Gloucester Schooner Festival .

Witness the majestic schooners, both historic and modern, as they gather in Gloucester Harbor. The festival, complete with maritime-themed events and activities, pays homage to the town’s seafaring traditions and provides a unique opportunity to experience the charm of these classic sailing vessels.

Gloucester Schooner Festival is an annual event that takes place at the end of August and the beginning of September. Check the site for more details.

Attend the Gloucester Block Party

Join the vibrant community atmosphere at the Gloucester Block Party , a lively street festival that takes over downtown Gloucester, typically at the end of summer.

Experience live music, local art, food vendors, and a festive atmosphere as the town comes together to celebrate. The Gloucester Block Party offers a dynamic and entertaining experience, showcasing the town’s cultural diversity and creative spirit.

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Hike the Ravenswood Park Trails

Another outdoorsy thing to do in Gloucester MA is to escape into nature by exploring the trails of Ravenswood Park , a pristine wooded area with a network of hiking paths.

Wander through lush forests, cross wooden bridges, and discover scenic overlooks that provide breathtaking views of Gloucester’s landscapes.

Operated by Trustees of the Reservation. Admission is free, and it’s suggested to allow at least two hours to explore. ( 481 Western Avenue )

Discover Gloucester’s Literary Legacy at the Sargent House Museum

Step back in time at the Sargent House Museum and discover Gloucester’s rich literary legacy.

Explore the beautifully preserved historic house, once home to notable figures like Judith Sargent Murray. Delve into the town’s intellectual history, which played a significant role in shaping early American literature.

The Sargent House Museum offers a glimpse into Gloucester’s past, making it a must-visit for history and literature enthusiasts alike. The museum is open during summer and fall weekends starting on Memorial Day weekend. ( 49 Middle Street )

See related:

Top 23 Best Things to Do in Rockport MA

Top 29 Best Things to Do in Newburyport MA

Top 7 Best Things to Do on Plum Island

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About Kerry Flatley

Kerry Flatley has lived in New England for the past 26 years. She has roots in Maine & Massachusetts, family in New Hampshire, and grew up close to the Connecticut border. She loves all that this region has to offer – the ocean, mountains, islands, history, villages, and cities. When she’s not writing about New England, she’s relaxing at home in the Boston suburbs with her two teenage daughters and husband.

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10 Things to do in Gloucester MA on a Day Trip or Weekend Getaway

The historic fishing village of Gloucester, Massachusetts makes an excellent day trip from Boston or a perfect weekend getaway in New England . America’s oldest seaport, this charming New England coastal town oozes historic charm with an authentic mix of working fishermen, artists, and visitors.

While people used to visit to see the port made famous by the George Clooney movie The Perfect Storm , today TV fans visit to see the bluefin fishing boats featured in the Nat Geo show Wicked Tuna . There are plenty of fun things to do in Gloucester to fill a day or even a weekend, depending on how much time you might want to spend on the beach or the season when you are visiting.

Best Things to do in Gloucester, MA

Whether you have a day in town or you are splitting your weekend between Gloucester, Rockport, or Salem , here are the top things to do in Gloucester MA.

Take a Whale Watching Cruise

It is impossible to appreciate a historic, fishing village such as Gloucester without getting out on the water, following the path of so many that have come before. Luckily there are many options available, depending on your budget, interests, and time available.

Gloucester offers some of the best whale watching in the world, with humpbacks and minke whales making regular appearances. 7 Seas Whale Watch , which leaves right from downtown Gloucester, offers two sailings a day to Stellwagen Bank National Marine Sanctuary — with guaranteed whale sightings! This family-run business has been offering whale watching tours for three generations over seven decades.

7 Seas typically offers sailings from mid-April through mid-October but be sure to check the website for current schedules.

Whale watching is also available from Cape Ann Whale Watch aboard the largest, fastest ship in Gloucester.

Enjoy a Schooner Sail

There are a number of historic schooners that offer private or public sailings out of Gloucester, including the Schooner Thomas E. Lannon .

The Schooner Thomas E. Lannon runs a variety of sailings, including a two-hour sunset sail. Be sure to check the website for the schedule and any specials they might offer such as “Saturday morning kids sail free” or Tuesday’s “half off a second ticket” deals.

Explore Using the Harbor Shuttle

If you want a cheap way to get out on the water or you are taking an impromptu trip to Gloucester, the water shuttle is a perfect option. It leaves from two downtown ports and The Studio restaurant in Rocky Neck. Tickets provide all-day hop-on / hop-off privileges or you can stay on for a harbor tour as it moves from port to port.

Advance tickets are not required, you can check out the schedule at the dock at St. Peter’s Marina or Solomon Jacobs Public Landing in Harbor Loop.

Of course, if you really want to feel the connection to Gloucester’s fishing culture, you can go deep-sea fishing. Half and full-day public and private charters are available from Adventures at Yankee Fleet .

Fishing charters head out to Stellwagen Bank and Jeffrey’s Ledge, where you can catch haddock, pollock, cusk, hake and redfish, and halibut, and currently one cod per person.

Visit the Artist Colony on Rocky Neck

Located in Gloucester’s Inner Harbor, Rocky Neck is the oldest working art colony in the United States. You can visit to browse the shops and art galleries that line the streets or pop into the studios that might be open to watch the artists at work.

To get to Rocky Neck, you can take the water shuttle to the stop at The Studio restaurant (and have lunch before or after exploring the area.) If you are driving, free parking is available in a parking lot on Rocky Neck just after turning onto Rocky Neck Ave. Street parking is also available.

Walk Along the Harbor

When you arrive in Gloucester, stop by the Visitor Welcome Center at Stage Fort Park. You can then park along the road and walk along the Harbor Walk along Stacy Blvd. towards downtown. Kids especially will love watching the drawbridge go up and down to let through boats at the Cut Bridge.

This is also where you will find the iconic Gloucester Fishermen’s Memorial. Designed by English sculptor Leonard F. Craske, this eight-foot-tall, bronze statue of a fisherman dressed in oilskins stands braced at the wheel on the sloping deck of his ship and is looking out over Gloucester Harbor. The memorial is dedicated to “They that go down to the sea in ships” from 1623 to 1923. The plaques surrounding the memorial remember fishermen from Gloucester who were lost at sea.

Before you get to that more famous memorial, you will also come upon the Fishermen’s Wives Memorial . This statue honors the women who have been the soul of fishing communities.

Take a Foodie Tour

Without question, Gloucester is home to some of the freshest and tastiest seafood. But if you take some time to explore downtown Gloucester along both Rogers and Main Street, you will find cool coffee shops, an Italian bakery that will have you following your nose as your mouth waters, and all sorts of restaurants offering outdoor dining.

Either explore on your own or take a food tour with Cape Ann Foodie Tours. I always love a good food tour, and the Taste of Gloucester tour stops at five or six local vendors to try chowder, bacon-wrapped scallops, beer tastings, Italian cannoli, and a sandwich that is a favorite of locals. Along the way, you can learn more about the 400-year history of Gloucester.

Visit Cape Ice

Cape Pond Ice Company has been icing Gloucester’s fleet since 1848, producing up to 150 tons of ice a day, including 300-pound blocks. You can take a tour of the facility, purchase ice, or visit the gift shop. Plus, you can check out any fishing boats being loaded with ice and peek inside the refrigerated “icehouse”.

Sun Bathe on Good Harbor Beach

There are a number of small beaches accessible from the downtown area, including Half Moon Beach out by Stage Fort Park. However, the most famous and arguably nicest beach is Good Harbor Beach, located out of town. Keep in mind that parking is restricted to town residents with permit stickers only and streets are blocked off for parking to limit out-of-town visitors crowding local beaches.

However, if you are staying for the weekend, you may want to consider a vacation rental within walking distance to the beach or one that comes with a permit.

Drive Atlantic Rd. to Rockport

If you enjoy a scenic drive, or shopping, drive along the coast on Atlantic Road up to the nearby town of Rockport. The drive offers beautiful views of the rocky coast of Cape Ann, including lighthouses, and the houses that line the cliffs will give you serious house envy! Keep in mind that there is no street parking along this stretch.

Once in Rockport, there is plenty of paid parking throughout town (pay at the kiosk) for you to get out and explore. If you just have a short time, spend it in Bearskin Neck. This highly-touristic area offers so many cute shops, galleries, and restaurants. Grab some ice cream at Sunday’s (go early for their homemade waffle cones!) or pick up a lobster roll to go at Roy Moore Lobster Co.

Leave yourself time to walk to the end of Bearskin Neck and across the breakwater jetty for a great photo opp of the Rockport Harbor.

Where to Eat in Gloucester, MA

Blue Collar Lobster

If you are looking for a casual lunch option, eat on the deck at Blue Collar Lobster company for the freshest seafood. Order at the pickup window and then find a table on the covered patio on the water. Bar service is also available. Check for daily specials and pricing, but I can attest to the fried clams being excellent. The batter is very light but crispy, just the way I like it.

Blue Collar Lobster is located at 63 Rogers St, Gloucester, MA 01930 next to the Gloucester House.

Minglewood Haborside

If you want something a little more upscale, but still would prefer to dine outside on the water, Minglewood Harborside is the pick for seafood and sushi. Open for dinner during the week and lunch and dinner on the weekend, Minglewood offers live music, fun drinks, and a stylish setting.

Minglewood Harborside is located at 25 Rogers St, Gloucester, MA 01930.

When you are visiting Rocky Neck, stay for lunch or dinner on the outdoor patio at The Studio. Located right where the water shuttle picks up and drops off for your convenience, The Studio offers seafood, sushi, cocktails, and frequent half-price specials on appetizers.

The Studio is located at 51 Rocky Neck Ave, Gloucester, MA 01930.

Where to Stay in Gloucester

Note: This post contains affiliate links. If you click a link and make a purchase, I may receive a small commission at no cost to you.

If you decide to make a weekend out of your trip to Gloucester, there are many vacation rental options, some within walking distance to the beach. If you are looking for hotel options, you can’t beat the location of the Beauport Hotel . This upscale property is located right on the beach in downtown Gloucester, offering the best of both worlds in terms of water views and an easy walk through town.

For a romantic getaway, you may want to try the Harborview Inn located downtown. This small inn offers cozy charm with easy access to restaurants and shops in town.

Getting to Gloucester and Parking

Gloucester is 45 minutes north of Boston on Cape Ann. You can take an MBTA train from Boston’s North Station to Gloucester. From the train station, it is a five-minute walk into downtown.

However, if you are arriving by car, you will want to take Interstate 95 to Rt. 128 North to Gloucester. Make your first stop at the Visitor Welcome Center at Stage Fort Park to pick up maps and brochures, ask questions, and plan your day. There is short-term parking at the Visitor Center and a paid parking lot across the street for those who want to spend time on the beach or park. Keep in mind that currently beach parking around Gloucester is restricted to residents with permits only.

There are multiple places in town. Street parking is available along Western Avenue for one or two hours if you can find it. Street parking downtown requires you to pay at the kiosk. There is one small free parking lot downtown and another, larger paid lot off Rogers Street.

Visiting Massachusetts? You may also be interested in…

• Fun things to do on Cape Cod in the off-season
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• Things to do in the Berkshires with kids in the summer
• Things to do in Springfield MA
• Things to do in Plymouth
• Winter getaway in the Berkshires
• Things to do in Salem
• Massachusetts bucket list
• Christmas in Massachusetts

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Tamara Gruber is the Founder and Publisher of We3Travel. A former marketing executive and travel advisor, Tamara is an award-winning travel writer and recognized expert in family travel. Tamara is a member of SATW and the Adventure Travel Trade Association, and serves on the Board of the Family Travel Association. She is also the publisher of YourTimetoFly.com and the co-host of the Vacation Mavens travel podcast.

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Publish Date: August 7, 2024

2 thoughts on “10 Things to do in Gloucester MA on a Day Trip or Weekend Getaway”

What about the Gloucester House restaurant?

Well, it sounds like a dream vacation for me. Sailing with schooners, taking a walk along with the fresh breeze, and eating seafood than what else you need? Further, if you are recently coming out of lockdown because of COVID-19 then a visit a Gloucester is all you need.

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The 10 Best Things to Do in Gloucester, Massachusetts

Gloucester (pronounced "glaw-ster"), Massachusetts, is the oldest fishing port in America. Located on Cape Ann, just 40 miles north of Boston , the town is fiercely proud of its 400-year history and role in the fishing industry. Gloucester gained public attention in the Hollywood film "The Perfect Storm" and the reality TV series "Wicked Tuna." Despite the media attention, this fishing town stays close to its roots, making it the perfect destination for a look into authentic New England living.

See the Gloucester Fisherman's Memorial

Gloucester fisherman's memorial.

It's estimated that 10,000 Gloucester fishermen have died at sea. Those lost lives are commemorated by the Gloucester Fisherman's Memorial, commonly known as "The Man at the Wheel." Commissioned in 1923 during Gloucester's 300th-anniversary commemoration, the monument has since become the city's iconic symbol. The 8-foot-tall fisherman, cast in bronze, has looked out over Gloucester Harbor from his position on Stacy Boulevard since 1925.

Go Whale Watching

Gloucester's proximity to Stellwagen Bank and Jeffreys Ledge—two nutrient-rich areas on the ocean floor that are like banquet tables for whales—make it one of the best New England ports for a whale watching voyage. Several whale watching companies offer frequent departures from Gloucester during the season when whales are feeding: typically mid-April through October.

Both ​ Cape Ann Whale Watch and 7 Seas Whale Watch guarantee whale sightings, which means if you don't spy a whale, you'll be offered free tickets for a future trip.

Play on Good Harbor Beach

Good harbor beach.

While Gloucester has several beautiful beaches to explore, Good Harbor Beach is the prettiest. In addition to views of the Twin Lighthouses on Thacher Island and of smaller Salt Island (which you can walk to at low tide), you can surf the waves or walk the sand year-round. Good Harbor is an ideal spot to swim, boogie board, play beach volleyball, and build sandcastles in the summer.

If you book a stay at Blue Shutters Beachside Inn , you'll be steps from Good Harbor Beach with an incredible ocean view right from the living room couch.

Visit Rocky Neck Art Colony's Studios and Gallery

Courtesy of Discover Gloucester

The Cultural Center at Rocky Neck

There's something about the light in Gloucester and this rocky peninsula's natural beauty that has beckoned to artists for nearly two centuries. Don't miss the chance to see artists at work and shop for their one-of-a-kind creations at Rocky Neck Art Colony , the oldest continually working art colony in America. There are 15 galleries on this waterside strip of land where visitors can browse work by painters, photographers, potters, jewelry makers, and textile designers. Float Gallery is a new addition to the scene that features new work by local artists. The exhibitions change each month.

East Gloucester is home to five studios specializing in woodworking, ceramics, watercolor painting, sculpture, and more if you need more art in your life.

Feast on Fresh Seafood at Gloucester House

Courtesy of The Gloucester House

Blue Collar Lobster

You'd be missing out if you visited Gloucester and didn't sample some fresh-caught Atlantic seafood. Commercial boats catch haddock, cod, tuna, and New England's favorite crustaceans: lobsters. ​The Gloucester House, a fixture on Seven Seas Wharf since 1958, is a reliable place to satisfy your seafood cravings, from raw oysters to pan-seared tuna to lobster rolls, served either warm with butter or chilled with mayo and celery. Lobster pie, lobster carbonara, even lobster stuffed lobster—the menu is loaded with indulgences, and the service is warm and welcoming.

Be Amazed by the Wonders of Hammond Castle

Courtesy of Hammond Castle Museum

Hammond Castle

Gloucester is home, oddly enough, to a medieval-style castle. This fortress on the coast built with Cape Ann granite was completed in 1929 for prolific inventor and avid art collector John Hays Hammond Jr. Several of the castle's windows, stone archways, and wooden facades were a part of Hammond's collection and date as far back as the Classical period.

On a self-guided tour of Hammond Castle, you'll see marvels like the Great Hall's organ with its 8,200 pipes and a 30,000-gallon swimming pool that can be switched from fresh to saltwater with the switch of a lever. The attraction's season ends each year with Holidays at the Castle when Gloucester businesses and organizations deck the halls. Special events include a craft fair, holiday concerts, and a visit from Santa Claus.

Explore Maritime Art and History at Cape Ann Museum

Courtesy of Cape Ann Museum

Founded in 1875, this cultural institution documents centuries of maritime art inspired by Cape Ann and the rest of the region. It boasts the most extensive collection of Fitz Henry Lane (a Gloucester native), along with works by John Sloan, Katharine Lane Weems, and Milton Avery. The museum also highlights works from current-day Cape Ann artists.

Beyond fine art, the museum's campus is home to two sculpture gardens, a 19th-century captain's house, and a library.

Cape Ann Museum

Dine overlooking the water at the beauport hotel, beauport hotel gloucester.

Gloucester's swanky Beauport Hotel, which opened in 2016, offers a bit of luxury in this rough and tumble fishing town. Even if you don't stay overnight (the rooftop pool, whirlpool, and bar will sure make you want to in the summer), be sure to make a reservation for dinner. There are phenomenal water views at 1606 Restaurant & Bar and creative cocktails and a menu that features predominantly steaks and seafood, including raw bar selections. There's live music in the cozy bar every Wednesday and Thursday evening.

Walk Through the Home of a Famous Interior Designer

Courtesy of Beauport, the Sleeper-McCann House

Beauport, Sleeper-McCann House

Henry Davis Sleeper was one of the first professional interior designers in the U.S., and his Gloucester summer home offers a unique look into his life and interests. Beauport, the Sleeper-McCann House took decades to complete and evolved throughout Sleeper's life. After he died in 1935, the house was preserved much as he left it. Now a museum and a National Historic Landmark, visitors can tour the mansion and explore each of the highly-decorated rooms. There are more than 40, and no two are alike!

See Gloucester From the Water

Courtesy of Schooner Adventure

One of the best ways to truly experience life in Gloucester is on the water. Whether you want to take a scenic sail aboard a historic schooner , enjoy a narrated cruise through a tidal estuary, or charter a fishing excursion, there's a Gloucester boat for you. Many of Gloucester's boat operators offer private charters if a public tour isn't appealing.

Fans of the National Geographic show "Wicked Tuna" can join a charter fishing trip aboard F/V Hard Merchandise , Captain Dave Marciano's ship. Charters run from April 15 to July 10, and if you catch a giant tuna, you can get a cut of the sale.

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The 15 Best Things to do in Gloucester, Massachusetts

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Visiting Gloucester, Massachusetts isn’t what you might imagine for a beachside retreat. You won’t find luxury hotel chains here, nor will you find tropical cocktails on rooftop bars. Instead, you’ll find friendly, community-oriented people who love their home and are thrilled to be able to share it with you.

Gloucester is a strong fishing hub, so much so that many of the residents you meet likely are in the fishing industry or at least have family who have braved the rough sea. But in addition to being dedicated to maritime culture, you’ll find that Gloucester is filled with stunning art and architecture, delectable sweets and treats, and a multitude of ways for you to be at one with nature.

From beach days to evenings on the open sea, there are just so many fun things to do in Gloucester, MA. With so many options, you might not know where to begin. So we’ve compiled our list of the absolute best things to do in Gloucester for you. Stick to these fun and unique Gloucester bucket list recommendations, and there’s no doubt you’ll have a fantastic time exploring this friendly seaside haven!

Disclaimer: This post may contain affiliate links. If you make a purchase or booking through one of our links we may earn a small commission (don’t worry, it’s at no extra cost to you).

The 15 Best Things to do in Gloucester, MA

1. sail on the schooner lannon.

The Schooner Thomas E. Lannon has been a part of Gloucester’s history since 1997, but its origins date back further than that. The boat is named after the owner, Tom Ellis’ maternal grandfather, who fished out of Gloucester from 1901 to 1943. The Schooner Lannon was designed to make you feel like you were sailing on a fishing schooner a hundred years ago.

These days, the boat offers two-hour sails and private charters from mid-May to mid-October, and these sails are some of the most unique things to do in Gloucester. When you climb aboard, you’ll be delighted by the views of Gloucester’s working harbor and the rocky coastline. 

You’ll take in lighthouses, beautiful beaches, and even historic castles. Unlike some other boat tours, this isn’t designed to be an educational journey. There’s no narrator on board. Instead, it’s just meant to be a peaceful cruise where you can be at one with the sea.

In addition to the standard cruises, there are also featured events throughout the year. Be prepared to boogie on the water with the Sunset Music Cruises. Or enjoy the atmosphere on a Moonlight or Stargazing Sail. If you’re visiting around the Fourth of July or during Labor Day weekend, you can join for a dessert cruise and take in the show during the Fireworks Sails. 

There’s also one very special sail that happens during the Gloucester Schooner Festival Race, which is held every Labor Day weekend. The Schooner Lannon always takes part in this race, and you’re invited on board. Join in for a day of adventure, fun, and one-of-a-kind views!

2. Spend a Day on Good Harbor Beach

As a seaside town, it’s no surprise that Gloucester boasts plenty of beautiful beaches. But one of the area’s top spots is Good Harbor Beach. Here you’ll find powdery white sand and astounding views, with rocky shores overlooking the water.

During low tide, you can walk out to Salt Island, a natural wonderland with no real trail system that requires a bit of a sense of adventure. You can climb to the rocky summit to take in the view of the mainland. Then, during high tide, you can get back to relaxing as you bob in the clear blue water’s waves. 

3. Tour the Old-World-Style Hammond Castle

Open from April until the winter, the Hammond Castle Museum is a bit of an anomaly, which is what makes it one of the top things to do in Gloucester, MA. Most visitors to Gloucester don’t expect there would be a European castle on Cape Ann. But indeed, there is one, thanks to John Hays Hammond, Jr., a scientist, inventor, and art connoisseur who had a passion for the art and architecture of old European styles.

Today, Hammond’s Castle is a museum displaying the treasures he collected throughout his travels and showcasing the fine old-world-style architecture he so adored. You can book yourself a tour or take yourself on a self-guided journey into the past. 

But there are also special tours and events to join if you visit at the right time. During the summer and through Halloween, you can take a Thursday Night Spiritualism Tour, a candlelight tour that honors the American Spiritualism Movement, of which Hammond was a firm believer. You’ll learn all about cultural phenomena like spirit photography and more scientific achievements like Hammond’s work with ESP.

Or, if spiritualism isn’t your thing, you can take a Thursday Night Candlelight Tour instead, which is available from September to the end of December. You’ll learn more about the Hammond family itself and about how they built the castle.

During the summer, you can also have your own picnic on the ocean-facing lawn. And for those who love medieval history, the museum offers a lecture on the History of Medieval Arms and Armor.

4. Go Lighthouse Hopping

Up for a drive? Cape Ann is home to five iconic lighthouses, symbols of the area’s maritime history. And if you’re a lover of history and beautiful architecture, taking a lighthouse tour is a must-do thing to do in Gloucester.

To see Annisquam Harbor Lighthouse, head to Wingaersheek Beach and enjoy the view. Over on Ten Pound Island in Gloucester Harbor, you’ll find the aptly named Ten Pound Island Lighthouse. And over in the eastern part of Gloucester, you’ll see the Eastern Point Lighthouse. For the best view of this lighthouse, head to Dog Bar Breakwater.

Just a mile offshore of neighboring Rockport, you’ll discover Thatcher Island, which is home to the Thatcher Island Twin Lighthouses. The south tower has a red light flashing five times every 20 seconds. But the north tower has a steady amber light in honor of those who passed at sea. Also in Rockport, you’ll find the Straitsmouth Island Lighthouse, built upon what is now a 31-acre bird sanctuary.

5. See a Show at the Theater

Gloucester firmly supports the arts, and one of the top things to do in Gloucester, MA, is to take part in the arts and culture of the area. At the Gloucester Stage Company , you’ll find local actors perfecting their craft in intimate productions. This non-profit theater company puts on both contemporary plays and beloved classics inside a century-old warehouse on the Gloucester shore. 

These can’t-miss shows are a perfect way to spend an evening. From rousing comedies to heartbreaking dramas, every performance goes to show how much a night at the theater can affect you, whether you’ll be in tears from laughter or from the emotional performances of these talented actors. 

In addition to their lineup of plays, each year also brings about NeverDark, a series of one-night-only shows performed by world-class actors, comedians, writers, and directors.

6. Sample the Best Ice Cream in Town

Is there anything better than a day at the beach? Yup, it’s a day at the beach with an ice cream in hand. While Gloucester boasts plenty of ice cream shops that’ll help you satisfy your sweet tooth cravings, there’s one shop that you absolutely need to add to your Gloucester bucket list: Holy Cow Ice Cream Cafe .

This award-winning ice cream cafe specializes in ice cream for everyone. Want a childhood favorite mixed into your ice cream? How about an ice cream loaded with Little Debbie’s Cosmic Brownie chunks? Want a Massachusetts staple made in a new way? Try the Boston Cream Pie ice cream. Want to get a little tipsy? Try the whiskey-infused Tipsy Seagull!

It truly is a place for everyone to enjoy. There are plenty of allergen-safe flavors, as well as vegan options. There’s even plant-based peanut butter ice cream you can give to your pooch. So if you’re craving something sweet, you know that Holy Cow can provide you with exactly what you need.

7. Go Whale Watching

Going whale watching is a great way to see the best sights in Gloucester. You can spot whales anytime from May to October, but whale-watching boat captains in the area say that September may be the best month for sightings. 

What can you expect to see? According to Cape Ann Whale Watch , the most commonly spotted creatures are humpback whales, fin whales, minke whales, Atlantic white-sided dolphins, northern right whales, and harbor porpoises. Sei whales, blue whales, sperm whales, and long-finned pilot whales have also been spotted on occasion.

When you take a whale-watching tour with a company like Cape Ann Whale Watch, you’ll be led by naturalists with decades of experience who can take you to the top spots to see whales. In fact, this company so believes that you’ll see a whale that you are invited back on board for free for any number of trips until you do!

8. Take a Dinner Cruise

Want another way to get out on the water? Book your ticket on a dinner cruise. Beauport Cruiselines offers both lunch and dinner cruises that invite you to take in amazing views of downtown Gloucester, Ten Pound Island, Hammond Castle, and so much more. Sip wine on the upper deck as you admire the setting sun, then get ready to dine on upscale cuisine featuring locally-caught seafood. 

If you’re heading to Gloucester with a large group in tow, you can also book a private cruise. While public cruises typically happen during the summer or on special occasions, like their New Year’s Eve Cruise, private cruises are available all year round. When you book a Beauport Cruise, you’re guaranteed entertainment and a delicious meal on every journey.

9. Sample Local Fare On a Food Tour

Cape Ann Foodie Tours are walking culinary and cultural tours through cities located on Cape Ann, and that includes Gloucester. If you love trying the local cuisine everywhere you go, this is one of the best Gloucester activities.

You have two tour options in Gloucester. The first is the original “Taste Gloucester” tour. You’ll make your way on foot through downtown Gloucester as you sample food from five to six vendors. What can you expect to dine on? From local chowder to bacon-wrapped scallops to Italian cannolis, you’ll be in for some serious treats!

Another option is the “Ales & Tales” tour. You’ll be taken to several local Gloucester watering holes, where local fishing captains will thrill you with stories of the sea. From wild storms to run-ins with Russians, you’re guaranteed to be on the edge of your seat. With the fishing industry being so deeply entrenched in Gloucester’s culture, this tour is a perfect way to learn more about what it means to be at sea.

10. Enjoy the Art at Rocky Neck

Just like fishing is such a big part of Gloucester’s community, so too is art. And visiting the Rocky Neck Art Colony is one of the coolest things to do in Gloucester. 

Located on a peninsula in Gloucester’s harbor, Rocky Neck is known for its rich cultural history and spirited community. From plein air artists like Winslow Homer and Childe Hassam to modernists like Milton Avery and Nell Blaine, artists of all kinds have lived on, worked on, and were inspired by Rocky Neck. Throughout the year, you can find everyone from potters to painters to jewelry makers displaying their work here. 

Many of the galleries close for a winter break, so it’s often best to visit during the warmer months. During the summer, you’ll typically see all 16 galleries open, with eclectic pieces bringing vibrancy to the colony. You’ll also find places to eat with gorgeous views, one-of-a-kind boutiques, and a floating tiki bar available for charters.

To get to Rocky Neck during the summer, a water shuttle runs from downtown Gloucester, arriving at the dock 35 minutes past the hour every day from noon to 5 pm. In the spring and fall, the shuttle is only available on weekends and only between noon and 4 pm.

11. Celebrate the Patron Saint of Fishermen

Gloucester has a passionate Italian-American community, and that community is responsible for the creation of St. Peter’s Fiesta , held for five days every June. One of the most fun Gloucester activities, it’s a celebration of Gloucester’s fishing history and faith. St. Peter is the patron saint of all fishermen and was considered the Catholic Church’s first pope. 

This family-friendly festival is filled with all kinds of entertainment for every age. Watch the community parade through the city streets with statues honoring their heritage and history. See the commercial fishing fleet be blessed. During the annual Seine Boat Race, root for the Nina, the Pinta, or the Santa Maria. Take part in the Fiesta 5K. And take your kids to performances of storybooks that come to life. 

But likely the highlight of the festival is the annual Greasy Pole competition, where you’ll see one of the best sights in Gloucester. This truly unique contest takes place 200 feet off Pavilion Beach. 

A 45-foot telephone pole is attached to a platform and extended out over the water, with a red flag nailed to the end. Then, the pole is greased. And so begins an incredible performance where contestants do all that they can to, one by one, take on the pole and capture the flag.

12. Go for a Scenic Hike

Taking a hike offers a great chance for Gloucester sightseeing. And there are plenty of beautiful, scenic hikes to go on throughout the Cape Ann area.

One of the best spots for hiking in Gloucester is Ravenswood Park, which includes a 2.3-mile loop trail perfect for beginner hikers. But there are also more trails available for anyone of any skill level. No matter what season you visit this park, you’re bound to be enthralled by its beauty, from the vibrant leaves in fall to the wildflowers in bloom in the spring.

Over in Mount Ann Park, you can stroll past Dykes Pond and head up the hill to a granite summit, providing you with a stunning view of Cape Ann. Or, for a more seaside walk, you can head to Rafe’s Chasm, which offers two different experiences. New hikers should take the shorter trek to the ocean, where you’ll find clifftop views of the Atlantic. 

But if you’re a more experienced hiker, you may want to try to reach the chasm itself. It’ll require you to climb over several rocks, so you should only do this hike if the weather is fair and there’s no danger of slippery ice or water. But if you decide to take the more challenging road, you’ll be rewarded with breathtaking rock formations.

13. Tour Downtown During a Gloucester Block Party

Visiting downtown Gloucester is a must-do thing to do when you visit this historic little city. You can take the HarborWalk, which is marked by 42 story posts, the first being in St. Peter’s Square. 

The HarborWalk takes you through historical and cultural points around the city, like the beloved Fisherman’s Memorial statue, which honors all the fishermen lost at sea. Throughout downtown, you’ll find art galleries, restaurants, shopping, theaters, museums, historic homes, and so much more. 

There’s never a bad time to do the HarborWalk, but perhaps the best time to visit the downtown area is during the Main Street Block Parties. Occurring Friday nights throughout the summer, you’ll partake in live entertainment from local bands, street performers, children’s activities, and al fresco dining, in addition to seeing all that downtown has to offer throughout the year. 

It’s a perfect way to spend a summer evening with your family and a great way to take in some Gloucester attractions.

14. Explore Tide Pools at Wingaersheek Beach

Good Harbor isn’t the only gorgeous beach you can find in Gloucester. Wingaersheek Beach is a little further off the beaten path, but it’s worth the venture. Running along the Annisquam River and Ipswitch Bay, Wingaersheek Beach is perfect for spending a day soaking up the sun.

One of the best times to visit this beach, called Winga by locals, is during low tide when a long sandbar is exposed alongside different rock formations. As the water retreats nearly a mile, you’ll spot tons of tide pools, with sea creatures going about their days. You’ll need to be careful and leave them to what they’re doing, but you can observe them and marvel at their beauty.

Also on Winga are various larger rock formations, with boulders juxtaposed against the white sand. After you’re done tide-pooling, you can go for a climb and explore the rocky perches. 

15. Peruse the Independent Bookstore

Perhaps one of the best things about Gloucester is that it celebrates its residents and the things that they create. From art galleries to restaurants, you’ll find few places that aren’t locally owned. 

And just like you won’t find many hotel or restaurant chains, you also won’t find many giant, internationally-owned bookstores. Instead, you’ll find quaint, independent bookstores. And visiting these shops is one of the most perfect Gloucester activities if you’re a book lover! 

The Bookstore of Gloucester is one such shop. This bookstore, located on Main Street, has been a part of Gloucester for over 45 years. This bright and cheery shop is a family-owned business dedicated to serving its community. You can even find a section of books from local authors.

Another great place to stop is Dogtown Books . Opened in 1997, this bookstore is run by a couple that believes in the connecting and healing nature of the written word. More than a store, it’s a community meeting place, with events happening all the time that encourage locals and visitors alike to get to know each other and be a part of each other’s journeys.

There you have it! The 15 best things to do in Gloucester, MA. What’s your favorite thing to do in Gloucester?

Planning a trip to Massachusetts? Check out our favorite books and travel guides!

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Jacqueline is a writer and editor pursuing the freelance life to explore the world. Born and raised in New Jersey, she spent her college years in Boston before settling down with her partner and puppy in Monterey, California. When she’s not writing, you can often find her planning her next trip. Road trips are her favorite, whether it’s driving across the country or simply exploring a new city in her own backyard. She loves uncovering the history of every new place she goes. Jacqueline has a restless passion for learning and makes it a goal to pick up a new skill every year. She’s picked up embroidery, crocheting, knitting, and cross-stitching, but she’s hoping to master more languages to help her in her travels. She’s also a published author, with short stories and poetry appearing in several anthologies.

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32 Fun Things to do in Gloucester

Excerpt from 32 fun things to do blog | written by addison choate.

With the anticipation of the warmer weather on the horizon, you may be thinking of planning a day trip or a longer stay to visit Cape Ann this Spring or Summer. No matter what time of year it is, our friends at Addison Choate have compiled 32 fun things to do in Gloucester, Massachusetts.

Here are 10 of the 32 fun and safe activities and destinations to discover in our historic seaport city. Read the full article at https://addisonchoate.com/32-things-to-do-in-gloucester/ .

GOOD HARBOR BEACH

With beautiful soft white sand, a large area to spread out, incredible views of the  Thacher Island lighthouse , and the ability to walk out to Salt Island during low tide, Good Harbor is a fantastic spot to spend a Summer day.

In the off-season you can still enjoy the beach and even bring your dog out for a run to burn off some of that extra energy. To learn more about Good Harbor you can read our  Definitive Guide To Good Harbor Beach

TAKE AN HISTORIC SAIL

The striking schooner was built in 1997 in Essex, MA. Framed with local white oak and black locust, the schooner has a length on deck of 64.5 ft and overall length of 90 ft.

The Schooner Lannon offers a variety of food options as well as beer, wine and other drinks to enjoy during the sail. It’s a fantastic way to get a different look at Gloucester harbor.

GET SOME FRESH SEAFOOD FROM A FISHMONGER

A few of our favorite local shops include:

Connolly Seafood: http://www.steveconnollyseafood.com/ Captain Joe & Sons Lobster: http://www.wholesalelobster.com/ Turners Seafood: https://www.turners-seafood.com/gloucester-market/

THE PERFECT STOP, FOR THE RECORD

If you’re looking to take a step back in time and find the perfect record or that CD that you used to love you have to take a trip over to  Mystery Train Records .

Located right on Main Street in Gloucester, Mystery Train has a great selection of rare & collectible vinyl from just about any genre you can imagine. Heck, they even have eight track tapes!

If you’re up in Gloucester, it’s definitely worth a stop!

SHOP AT INDEPENDENT BOOKSTORES

Dogtown Books offers a wide selection of preowned books, certified pre-owned books, and just general used books to choose from. They topics range from culinary adventures to space exploration and the owners are very friendly and welcoming.

The Bookstore of Gloucester on the other hand has been serving Cape Ann readers for over 45 years and offers the perfect local alternative to Amazon. It’s a great spot to pick up the latest releases and browse the curated collection.

If you are interested in Independent Bookstores take a closer look at our article on  5 Great Independent Bookstores on Cape Ann .

STEP BACK INTO MEDIEVAL TIMES

John Hays Hammond was a legendary inventor, holder of over 400 patents and is known as “The Father of Remote Control.” Visitors can tour the courtyard, great halls, secret passageways and war room and marvel at the beauty of the castle grounds.

In October, Hammond Castle even gets in the Halloween spirit with special haunted tours. If you fall in love with the castle you can even decide to host your wedding on site! It’s such a cool venue that it made our list of the  Top 5 Gloucester MA Wedding Venues .

VISIT EASTERN POINT LIGHTHOUSE

The current 36-foot tower was built in 1890 and has an attached 2 story keepers quarters. Eastern Point You will see images of Eastern Point in publications about Gloucester and the lighthouse was even home to Winslow Homer back in 1880.

You can drive out to the light, park and take the half mile walk out on the dog bar breakwater to the Dog Bar Lighthouse. It’s a beautiful area and a great spot for a sunset or sunrise. If you want to see some incredible footage of the lighthouse you have to check out this  Kenny Chesney video that was shot in Gloucester . 

HOP ON A FOODIE TOUR

What better way to explore the coastal cuisine of Gloucester, Massachusetts than on a foodie tour! Try a little bit of everything and learn about some of Gloucester’s hidden gems on the Cape Ann Foodie Tour.

From thick and tasty claim chowder to homemade olive oil and delicious Italian sandwiches, Cape Ann Foodie tour will expose you to the culinary delights of the area.

Learn more about their schedule and some of the stops here –  Cape Ann Foodie Tours

INTERIOR DESIGN MECCA

Perched on a ledge overlooking Gloucester Harbor is the home of one of America’s first interior designers, Henry Davis Sleeper. Beauport, the Sleeper-McCann House, was Sleeper’s summer retreat and the 40 room mansion houses Sleeper’s diverse collection of folk art, pottery, antiques and other artifacts.

A National Historic Landmark, each room is distinguished by a historical or literary figure and no two rooms are the same. The property even features a beautiful garden and a secret staircase. The Sleeper McCann House is open from late May to Mid-October and is definitely one of the best things to do in Gloucester.

TREK THROUGH THE DOGTOWN WILDERNESS 

With some incredible trails, Dogtown offers a great opportunity for hiking, biking, running, cross country skiing and an outing with your fur-friend. Along the paths you will find large boulders with sayings carved into them. These boulders were carved by unemployed Finnish quarrymen during the Great Depression who were commissioned by local entrepreneur Roger Babson.  There are 36 boulders that were carved with inspirational sayings such as “Never Try Never Win” and “When Work Stops Values Decay.” 

The name Dogtown is said to date back to the American Revolution and is derived from the dogs that the women kept while their husbands fought in the war. At one point it was estimated that there were anywhere from 60 to 80 homes in the area.  But after the war, the ports became safer, the fishing industry returned and so too did the settlers to the coastline. 

So if you’re in the mood for a journey off the beaten path, Dogtown is a great thing to do in Gloucester.  Here is a link to a great Dogtown Guide . 

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15 Best Things to Do in Gloucester, MA

By: Author Stefan Meyer

Posted on Published: February 14, 2023  - Last updated: May 28, 2023

Famous for the fishing industry, Gloucester is home to superb beaches and waterfront attractions.

With Gloucester Center as the highlight of the city, it is undeniably one of the most memorable trips you can have.

Make your travel planning a breeze by looking at the best things to do in Gloucester, MA, below.

1. Fishermen’s Memorial Monument (AKA Man at the Wheel Statue)

The Fishermen’s Memorial Gloucester, MA 01930

This 8-foot-tall memorial statue was designed by Leonard Craske and built in 1925.

Why You Should Go

Stopping by this historic cenotaph is one of the free things to do in Gloucester.

Learn about the fishermen who lost their lives at the sea while trying to provide for their families.

These anglers are the inspiration for the book, The Perfect Storm by Sebastian Junger and the film of the same name.

In addition, you can stroll along the beach and admire the scenic view surrounding the memorial sculpture.

If you’re traveling with your little ones, go whale watching by 7 Seas Whale Watch.

Sail through the waters with experts and witness these majestic creatures up close.

This iconic monument is also near numerous restaurants serving local and fresh seafood.

Head to Gloucester House, just a minute from the statue, by car for delicious lobster rolls, clam chowder, and other seafood meals.

2. Hammond Castle Museum

80 Hesperus Ave Gloucester, MA 01930 (978) 283-2080

Constructed in the late 1920s, this stately museum is the home and laboratory of the renowned inventor John Hays Hammond Jr.

Sited on a bluff overlooking the beautiful ocean, this medieval-style museum offers a fantastic view for visitors.

Not only that, but this castle also houses extraordinary exhibits from different centuries up to the present.

Don’t miss out on the collections and inventions of inventor Hammond for the unique things to see in Gloucester.

Check their website to know their schedule this season.

Since this castle is old, it’s not handicapped accessible.

There are a few steep, narrow, and spiral stairs to reach some parts of the museum.

So, avoiding these areas is best if you have mobility issues.

Moreover, ensure to take precautions if you’re visiting with kids.

Related: Best Restaurants in Gloucester

3. Beauport, the Sleeper-McCann House

75 Eastern Point Boulevard Gloucester, MA 01930 (978) 283-0800

Opened its doors to the public in 1942, Beauport, the Sleeper-McCann House was the summer home of prominent interior designer Henry Davis Sleeper.

Discover why this lovely estate is one of the cool attractions in Gloucester.

Experience a one-of-a-kind creation of Sleeper as you tour this impressive mansion with 40 rooms.

From avant-garde rooms to interesting historical artifacts, this fairy-tale-like property offers a unique experience for all visitors.

Look into their social media page to check their timetable.

You can also stop by Niles Beach, approximately three minutes from here, for a splendid sunset and Boston view.

However, you will need a resident sticker for parking.

Recommended Hotel Nearby: Beauport Hotel Gloucester

Also See: Falmouth: Things to Do What to Do in Cambridge

4. Wingaersheek Beach

Atlantic St Gloucester, MA 01930

Located in West Gloucester, this picturesque beach stretches to 0.6 miles long.

Because of its shallow tide, this pristine beach is one of the city’s wonderful places to go today.

Meet seagulls and other marine creatures, make sand castles, explore the waters during low tide, and play beach games.

Additionally, its soft and white sands are ideal for a relaxing walk along the beach.

Reservations are required for non-resident beachgoers.

Make reservations ahead of your visit to ensure your slot.

For a complete, fun experience, you can pack your food and picnic at the beach.

Recommended Hotel Nearby: Rockport Inn and Suites

5. Good Harbor Beach

99 Thatcher Rd Gloucester, MA 01930 (978) 281-9785

Situated in East Gloucester, Good Harbor Beach is a stunning beach that served as a fishing village in the past.

With its awe-inspiring view and exceptional swimming conditions, Good Harbor Beach is one of the nice places to visit in Gloucester.

From delicate white sands and several tidepools to incredible waves perfect for bodyboarding, this gorgeous beach has something for everyone.

To top that, you can walk to Salt Island, a small island of Cape Ann, during low tides.

If you are a non-resident visitor, you must make an online reservation at least a day before your visit.

Also, check their website to know when dogs are allowed within the premises.

Recommended Hotel Nearby: Atlantis Oceanfront Inn Gloucester

6. Stage Fort Park

24 Hough Ave Gloucester, MA 01930 (978) 325-5600

The first settlers of Stage Fort Park in 1623 built fishing stages upon their arrival, which led to the area being called Stage Head.

Don’t forget to swing by Stage Fort Park if you’re searching for downtown spots to visit in Gloucester.

It is the home to two beautiful beaches, Half Moon and Cressy, in the city.

Furthermore, it has tennis and basketball courts, baseball fields, playgrounds, and picnic areas.

You can even bring your four-legged friend to the dog’s park within the grounds.

It is perfect for an outdoor adventure with your partner, family, and friends.

While dogs are permitted in the park, your furry friend is not allowed on the beaches.

And remember to leash your dogs and clean up after them when visiting the park.

Although there are charcoal grills on the picnic benches, you can still bring your own picnic grill.

Related: Places to Visit in Massachusetts

7. Eastern Point Lighthouse

Gloucester, MA 01930

The construction of this historic lighthouse began in 1831 as a way for seafarers to navigate Boston Bay easily.

Do you have a knack for photography?

Capture the scenic view of the lighthouse and the ocean overlooking the horizon.

From sunrise to sunset settings, this tourist spot is phenomenal.

Plus, you can take a relaxing walk on the brick walls or fish on the jetty.

Seeing this spectacular attraction firsthand is a must to know why it is one of the well-known cheap activities to do near you.

You cannot enter the lighthouse because it is fenced and currently operated by the United States Coast Guard.

Don’t be discouraged by the private property signage at the entry point.

You can still drive ahead to the lighthouse, but remember to be within the speed limit.

Also See: Fun Things to Do in Truro, MA Activities in Sandwich

8. Long Beach Gloucester

Rockport Rd Gloucester, MA 01930

Befitting its name, Long Beach is a magnificent beach that extends to Rockport, a nearby town in Essex County.

With its stretchy shorelines, soft sand, and clear waters, this beach is a paradise for locals and tourists.

Not to mention the great waves that are perfect for bodyboarding.

This beach is also complete with restrooms, showers, and nearby restaurants.

Paid parking lots are available near the beach.

However, finding a space can be a hassle, especially if you arrive late.

On the other hand, a trip to Rockport can be one of your favorite things to do in Gloucester at night.

Approximately nine minutes from the beach by car, this neighboring town is filled with exciting nightlife and fun activities for every visitor.

Recommended Hotel Nearby: Addison Choate

9. Ryan & Wood Distilleries

15 Great Republic Dr Gloucester, MA 01930 (978) 281-2282

Founded by Bob Ryan and Dave Wood, this family-owned business has been producing top-notch spirits since 2006.

Witness how Ryan & Wood Distilleries craft their world-class spirits.

Learn from the experts and know their history.

To top that, you can sample some of their whiskeys, rums, and gins during your tour.

That’s why it’s one of the fascinating activities in Gloucester that will perk up your interest in liquors.

For a satisfying meal after your trip, head to Seaport Grille, just a five-minute drive from this shop.

This waterfront restaurant serves tasty, innovative seafood dishes like their signature lobster rolls.

10. Gloucester Fishermen’s Wives Memorial

107 Western Ave Gloucester, MA 01930 (508) 344-9225

Unveiled on August 5, 2001, this monument was dedicated to the mothers, wives, sisters, and daughters of Gloucester’s fishermen.

Take a relaxing walk on this iconic path to remember the lives of the fishermen’s families waiting for them at the shore.

The memorial statue, breathtaking ocean view, pretty flowers, and the flags surrounding the path make this site marvelous.

Indeed, its natural beauty and enriched history are why it’s one of the city’s noteworthy sights to see this weekend.

If you feel hungry after a stroll, drive to Mile Marker One, approximately two minutes from here.

With the combination of delectable seafood to steak meals and mesmerizing waterfront view, this women-owned restaurant is a prime eating spot for travelers.

Related: Things to Do in Massachusetts

11. Gloucester Stage Company

267 E Main St Gloucester, MA 01930 (978) 281-4433

This theater is located in the Twin Lights Garage, designed by Ezra Phillips in 1915.

Visiting the Gloucester Stage Company can be your all-time favorite indoor stuff to do when it’s raining or cold in the city.

This performing arts theater is a hit with its intimate yet spacious setting and sensational shows and performances.

It also has a refreshment bar offering light snacks and an excellent selection of beers, wines, coffees, teas, and sodas.

Parking lots can be an issue when visiting this quaint theater.

So, arrive early to secure a slot in nearby free parking spaces.

Additionally, keep in mind that seating may be crampy for big and tall visitors.

Also See: Chicopee Activities Fun Stuff to Do in Gardner

12. Main Street

Sited in Central Gloucester Historic District, Main Street is the city’s commercial downtown.

Having second thoughts on what to do in Gloucester?

Head to Main Street, home to numerous restaurants, specialty shops, antique stores, and other shopping boutiques.

Take a trip down memory lane as you scan the vinyl records and CDs in Mystery Train.

Meanwhile, you can visit the Dogtown Book Shop if you’re a book lover.

Expect a lot of walking as you traverse this bustling street and its nearby attractions.

Wear comfortable shoes and clothes to enjoy a fun-filled trip.

And don’t forget to pack extra clothes and towels when traveling with your young ones.

Recommended Hotel Nearby: The Wylie Inn and Conference Center at Endicott College

13. Maritime Gloucester

23 Harbor Loop Gloucester, MA 01930 (978) 281-0470

Maritime Gloucester has been providing maritime and environmental preservation since 2000.

Engaging with marine creatures is one of the fun things to do in Gloucester with kids.

And Maritime Gloucester is an ideal spot.

This museum is an excellent place for fun and learning, from hands-on activities to interesting maritime exhibits and aquariums.

What’s more, you can witness the epic annual race of schooners during the Gloucester Schooner Festival.

Since some of its attractions are not shaded, remember to wear hats and sunscreens when visiting this museum.

Also, restrooms are limited on the site.

So, it’s best to plan ahead of your visit.

Recommended Hotel Nearby: The Cabot Lodge

Related: Beaches in Massachusetts

14. Gloucester Fleet Deep Sea Fishing & Charters

75 Essex Ave Gloucester, MA 01930 (978) 559-1978

This family-run business boasts the “Lady Sea,” a boat originally constructed by A1 Construction in Florida.

Take your significant other on a cruise to experience one of the most romantic things to do in Gloucester for couples.

With a spectacular view and available amenities onboard, a trip to this excellent site is worth it.

You can also join their fishing trips or book your own charter for private events.

As you sail through the ocean, it’s best to wear comfortable clothes.

But don’t forget your windbreakers, sunglasses, hats, and sunscreens.

While refreshments are available onboard, you can bring your own food and drinks, except for alcohol.

Recommended Hotel Nearby: Harbor Light Inn

15. Schooner Adventure

23 Harbor Loop Gloucester, MA 01930 (978) 281-8079

Launched on September 16, 1926, the Schooner Adventure is a historical activity that represents American fisheries.

Experience what it’s like to sail through Gloucester Harbor with the help of an experienced captain and crew.

Hoist the sails and set off on a remarkable adventure in the city.

Even better, it is open 24 hours.

Truly, this must-see attraction can complete any list of the best things to do in Gloucester, MA.

Dress like a sailor to level up your maritime adventure.

Bring your own picnic lunch to satisfy your hunger during your two-and-a-half-hour journey.

Recommended Hotel Nearby: Harborview Inn

Related: Family Beaches in Massachusetts

Map of Things to Do in Gloucester

15 Best Things to Do in Gloucester, MA for [currentyear]

• Fishermen’s Memorial Monument (AKA Man at the Wheel Statue)
• Hammond Castle Museum
• Beauport, the Sleeper-McCann House
• Wingaersheek Beach
• Good Harbor Beach
• Stage Fort Park
• Eastern Point Lighthouse
• Long Beach Gloucester
• Ryan & Wood Distilleries
• Gloucester Fishermen’s Wives Memorial
• Gloucester Stage Company
• Main Street
• Maritime Gloucester
• Gloucester Fleet Deep Sea Fishing & Charters
• Schooner Adventure

13 Best Places and Things To Do in Gloucester, Massachusetts

Gloucester, Massachusetts, known as “America’s Oldest Seaport,” is a charming coastal city that offers a perfect blend of natural beauty, rich history, and vibrant culture.

1. Rocky Neck Art Colony

Image Source: https://www.tripadvisor.in/Attraction_Review-g41580-d108837-Reviews-The_Cultural_Center_at_Rocky_Neck-Gloucester_Cape_Ann_Massachusetts.html

Known as the oldest continuously operating art colony in the United States, Rocky Neck is a vibrant neighborhood brimming with art galleries, studios, and boutiques. Take a leisurely walk through this charming area and immerse yourself in the local art scene. The galleries showcase a diverse range of artwork, including paintings, sculptures, and photographs.

2. Cape Ann Museum

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Delve into Gloucester’s rich history and cultural heritage at the Cape Ann Museum. The museum features an impressive collection of artwork, artifacts, and exhibits that highlight the region’s maritime history, fishing industry, and artistic legacy. Don’t miss the iconic “The Man at the Wheel” statue, a symbol of Gloucester’s seafaring traditions.

3. Hammond Castle Museum

Image Source: https://www.tripadvisor.in/Attraction_Review-g41580-d260102-Reviews-Hammond_Castle_Museum-Gloucester_Cape_Ann_Massachusetts.html

Step into a medieval world at the Hammond Castle Museum. This unique attraction showcases the eccentric architectural and artistic vision of John Hays Hammond Jr., a prominent inventor and collector. Explore the castle’s stunning interiors, filled with medieval artifacts, a great hall, a courtyard, and a breathtaking view of Gloucester Harbor.

4. Essex Shipbuilding Museum

Image Source: https://www.tripadvisor.in/Attraction_Review-g41561-d2225988-Reviews-Essex_Shipbuilding_Museum-Essex_Cape_Ann_Massachusetts.html

Just a short drive from Gloucester, in the neighboring town of Essex, you’ll find the Essex Shipbuilding Museum. Discover the area’s shipbuilding heritage and learn about the construction of traditional wooden boats. The museum features interactive exhibits, historic photographs, and even boatbuilding demonstrations.

5. Eastern Point Lighthouse

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Take a scenic drive to Eastern Point and visit the Eastern Point Lighthouse. This iconic structure has guided ships since 1832 and offers spectacular views of the Atlantic Ocean. Enjoy a leisurely walk around the lighthouse, explore the surrounding park, and capture some memorable photos.

6. Stage Fort Park

Image Source: https://www.tripadvisor.in/Attraction_Review-g41580-d271966-Reviews-Stage_Fort_Park_and_Beach-Gloucester_Cape_Ann_Massachusetts.html

Explore Stage Fort Park, a historic site that offers a picturesque setting for outdoor activities. The park features walking trails, picnic areas, and panoramic views of Gloucester Harbor. Don’t miss the famous “Fisherman’s Memorial” statue, dedicated to Gloucester’s brave fishermen.

7. Fishermen’s Memorial Monument

Image Source: https://www.tripadvisor.in/Attraction_Review-g41580-d526430-Reviews-Fishermen_s_Memorial_Monument-Gloucester_Cape_Ann_Massachusetts.html

The Fishermen’s Memorial Monument, also known as the “Man at the Wheel” statue, is an iconic and poignant memorial located in Gloucester, Massachusetts. It stands as a tribute to the generations of Gloucester fishermen who have lost their lives at sea, honoring their courage and contributions to the city’s maritime heritage. The monument, created by sculptor Leonard F. Craske, was dedicated in 1925 and has since become an enduring symbol of Gloucester’s fishing community.

8. Beauport, the Sleeper-McCann House

Image Source: https://www.tripadvisor.in/Attraction_Review-g41580-d108829-Reviews-Beauport_the_Sleeper_McCann_House-Gloucester_Cape_Ann_Massachusetts.html

Beauport, the Sleeper-McCann House, is a captivating historic home located in Gloucester, Massachusetts. Built in 1907, it is renowned for its unique architectural design, eclectic interiors, and stunning views of Gloucester Harbor. The house was the lifelong project of its owner, Henry Davis Sleeper, a prominent interior decorator and collector of decorative arts.

9. Wingaersheek Beach

Image Source: https://www.tripadvisor.in/Attraction_Review-g41580-d3337040-Reviews-Wingaersheek_Beach-Gloucester_Cape_Ann_Massachusetts.html

Wingaersheek Beach is a stunning and popular beach located in Gloucester, Massachusetts. It is part of the larger Atlantic coastline on Cape Ann and is known for its natural beauty, family-friendly atmosphere, and unique tidal pool formations. Wingaersheek Beach offers a wide expanse of soft white sand, making it a perfect spot for sunbathing, picnicking, and beach games.

10. Good Harbor Beach

Image Source: https://www.tripadvisor.in/Attraction_Review-g41580-d108830-Reviews-Good_Harbor_Beach-Gloucester_Cape_Ann_Massachusetts.html

Good Harbor Beach is another beautiful and popular beach located in Gloucester, Massachusetts. It is widely regarded as one of the premier beaches in the area, offering a combination of natural beauty, wide sandy shores, and breathtaking ocean views.

11. Maritime Gloucester

Image Source: https://www.tripadvisor.in/Attraction_Review-g41580-d2173107-Reviews-Maritime_Gloucester-Gloucester_Cape_Ann_Massachusetts.html

Maritime Gloucester is a captivating maritime museum and educational center located in Gloucester, Massachusetts. It serves as a gateway to the city’s rich maritime heritage, offering engaging exhibits, educational programs, and interactive experiences that showcase Gloucester’s fishing industry, maritime history, and marine ecosystems. The museum is housed in a historic waterfront building, formerly the home of the Gloucester Sea Serpent newspaper.

12. Ravenswood Park

Image Source: https://www.tripadvisor.in/Attraction_Review-g41580-d2009020-Reviews-Ravenswood_Park-Gloucester_Cape_Ann_Massachusetts.html

Ravenswood Park is a scenic nature reserve located in Gloucester, Massachusetts. Spanning over 600 acres, it offers a tranquil and picturesque escape from the bustling city, providing visitors with an opportunity to connect with nature and explore its diverse ecosystems. The park is known for its lush woodlands, serene ponds, and well-maintained trails, making it a haven for hikers, nature lovers, and outdoor enthusiasts.

13. Sargent House Museum

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The Sargent House Museum is a historic house museum located in Gloucester, Massachusetts. It is named after its former resident, Judith Sargent Murray, a prominent writer, philosopher, and advocate for women’s rights during the late 18th century.

Gloucester, Massachusetts, offers a diverse range of experiences and attractions that cater to different interests and preferences. Whether you’re a nature lover, history enthusiast, art aficionado, or simply looking for a relaxing coastal getaway, Gloucester has something to offer.

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Our mission is to serve the 50+ traveler who's ready to cross a few items off their bucket list.

How To Spend A Perfect Weekend In Gorgeous Gloucester, Massachusetts

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• Weekend Getaway

Miles of rocky coastline peppered with lush green spaces, sandy beaches, and gorgeous vistas make Gloucester, Massachusetts, a perfect weekend getaway destination. Cape Ann newbies will be enchanted by the kick-back coastal vibe, and seasoned guests who have visited Gloucester before will head straight to their favorite beaches.

Gloucester’s history was built on the fishing industry, and it is still a thriving seafaring community.

Note: Some information in this piece was obtained during a sponsored press trip, but all recommendations are my own.

Things To Do In Gloucester

Gloucester’s northshore location makes it a great playground for escaping the workday worries, letting you shake them off for a few days or several weeks. The craggy coastline and numerous inlets, bays, and rivers offer fabulous on-the-water activities to keep you as busy or as relaxed as you choose.

Beaches Rule In Gloucester

The beach scene is what brings everyone to Gloucester for their summer vacation. You can read our Gloucester beach guide here.

Pro Tip: Beginning with the 2022 beach season, a new online non-resident beach parking reservation system will help reduce and streamline beach traffic. Yodel , a parking management app, allows non-resident beachgoers to reserve and pay for their parking space at Gloucester beaches up to 10 days in advance eliminating the first-come, first-serve parking system. 

Good Harbor Beach

Good Harbor Beach is a welcoming soft, sandy beach. It is a popular toes-in-the-sand spot for Gloucester visitors. At low tide, the beach is long and wide with plenty of room for everyone’s blanket.

Wingaersheek Beach

Wingaersheek Beach on the northern section of Gloucester is a gorgeous wide sandy beach punctuated by enormous boulders at low tide. It is out of the flow of downtown Gloucester Harbor, making it a wonderful spot to spend the entire day.

Pavilion Beach

Pavilion Beach is famous for the “Greasy Pole Challenge” held each year during the St. Peter’s Fiesta in June. St. Peter is the patron saint of netmakers, shipbuilders, and fishermen with this 5-day celebration that honors the fisherman saint.

Half Moon Beach

Half Moon Beach is a small, crescent-shaped beach accessed in Stage Fort Park . The rough sandy beach is reached by traversing carved stone steps leading down to the water.

Cressy’s Beach

Cressy’s Beach is another rocky beach in Stage Fort Park and offers wonderful views of Gloucester Harbor.

Tour Hammond Castle Museum

In the 1920s, John Hays Hammond, Jr. decided to build a medieval castle on the Gloucester coastline, now known as Hammond Castle Museum . During the ‘20s and ‘30s, Hammond made several trips to Europe to obtain remnants of crumbling castles securing stone archways, fireplaces, and religious artifacts. Hammond’s castle home is a showcase of eclectic pieces including the monstrous pipe organ that dominates one end of the Great Hall.

Known for his inventions and securing over 400 patents in his lifetime, Hammond was an engineering genius. He is renowned for his work with radio control equipment. The castle rooms showcase a life of wealth and eccentricity, leaving guests to wonder what it was really like to live in a modern medieval castle.

Explore Beauport, The Sleeper-McCann House

A National Historic Landmark and summer home of Henry Daivs Sleeper, Beauport is a decorator’s masterpiece. Sleeper was an interior designer who loved beautiful things. The rambling mansion is a series of one showstopping room after another.

The casual dining room with its long table and mismatched chairs, painted a seafoam green set off by the expansive windows overlooking the coastline, sits waiting for a party. You can envision the guests in light summer garb sipping sparking libations and nibbling on delicate appetizers while enjoying lively conversation. Conversely, the China Trade Room, decorated with Asia-inspired pieces including hand-painted Chinese wallpaper, gives off a completely different vibe.

Visiting the Sleeper-McCann House is a must for designers and others seeking a spark of inspiration. The McCann family purchased Beauport after Sleeper’s death and kept the home design unchanged.

Picnic At Stage Fort Park

Stage Fort Park is an inviting green space in the heart of Gloucester. Within the park, you can swim at Half Moon and Cressy’s Beaches, climb the enormous rocks for an impressive harbor view, and explore the remnants of the old fort. The park has a large number of picnic areas, fields, and walking paths for enjoying the outdoors. There are even on-site bins where you can deposit the coals from your barbeque — you need to bring your own grill.

Sail Away For A Whale Watching Trip

If you have never been out to Stellwagen Bank National Marine Sanctuary on a whale watching excursion, then it is time to put this on your must-do list. It is the spot in the northeast to view our whale population.

Several companies offer excellent trips including 7 Seas Whale Watch and Cape Ann Whale Watch .

Scope Out A Wicked Tuna Boat

National Geographic’s TV show Wicked Tuna is filmed out of Gloucester. Now in its 11th season, it has become a classic reality, one-bluefin-tuna catch at a time show.

Pro Tip: Want to catch a glimpse of one of the fishing boats on the show, or perhaps run into your favorite onscreen fisherman? Some of the show’s tuna boats are docked at Cape Ann’s Marina Resort .

Snap A Photo With The Fisherman

The Fisherman’s Memorial is synonymous with Gloucester. The patinanted statue gazes out to Gloucester Harbor intent on bringing his ship safely home. It is a poignant reminder of the perilous life of fishermen out on the ocean. Designed by sculptor Leonard F. Craske, the statue pays homage to the Gloucester fishermen lost at sea.

Restaurants In Gloucester

Fresh seafood, prepared simply, is a gift from the kitchen. You will find many dining options in the Gloucester area. Below are three favorites.

1606 Restaurant And Oyster Bar

When you are looking for a fine-dining experience with a beautiful ocean view, the 1606 Restaurant and Oyster Bar in the Beauport Hotel is an excellent choice. The dining room is dressed in elegant crystal and ocean blues bringing the brilliant colors and sparkle of the harbor indoors.

Starters set the tone for every meal, and the options here are perfect. The pan-seared crab cake with red cabbage and apple slaw is not only delicious, it is healthy too. Of course, the chowder is creamy and delicious. The fish fry and the baked haddock casserole shine on the entrée menu.

Mile Marker One Restaurant

When you put a modern twist on traditionally-classic dishes, you set the bar high. At the hip and casual Mile Marker One Restaurant , they offer the perfect storm: delicious food and outstanding views.

Nestled in the heart of the marina on the Annisquam River, you can watch the busy harbor comings and goings as you happily munch on delectable delights from the local waters. Starters like the sauteed mussels with sausage and garlic in a flavorful broth, or the carmelized pear and fresh burrata salad with greens and bacon are loaded with flavor. The signature horseradish-crusted haddock topped with super crispy leeks resting on herb mashed potatoes rivals the seared local tuna served with a mango, avocado, and macadamia nut salad and a silky cashew sauce. Add a chilled bottle of wine and you have marina dining perfection.

During the cooler seasons — everyone but summer — they have custom marina-made igloos for a semi-al fresco dining experience. The heated tents have window views of the harbor and create a private dining room for each party. The unique dining experience, enhanced by the water views, is the perfect addition to your Gloucester getaway.

George’s Restaurant And Bar

When you are in the mood for a charming neighborhood spot, George’s Restaurant and Bar fits the bill. Slightly off the main tourist area, George’s is open for breakfast, lunch, and dinner.

Their breakfast and brunch menu is extensive and hearty. There are eggs Benedict and scrambled, omelets, pancakes, and French toast options with something for everyone. The specialties like their buttermilk biscuits and gravy served with three eggs will feed the hungriest diner. A more healthful specialty, George’s Loaded Avocado Toast is a huge plate of avocado, bacon, spinach, onions, and two perfectly poached eggs topped with a tangy balsamic drizzle — it keeps guests coming back again and again.

Hotels In Gloucester

The key component to choosing a spot to rest your head in Gloucester is the view. Find a spot that offers you beautiful sunsets and sunrises that works for your weekend budget.

Cape Ann’s Marina Resort

Just outside of the hustle of the downtown area is Cape Ann’s Marina Resort . Cozy rooms with a coastal vibe are on top of the waterfront action. From the extended deck, you can dreamily watch the harbor boats come and go, hear the chatter of local fishermen, and look on enviously at the yachts slicing through the local waters.

Enjoy a relaxing long weekend stay and a room with a gorgeous view, perfect for relaxing after a day at the beach. You can dine on-site at Mile Marker One and then stroll along the docks to watch the picturesque sunsets on the rippling water.

The resort is undergoing a complete renovation of their guest rooms (several under restoration at a time), ushering in a modern and casual beachy resort feel.

Rental Home Near The Beach

When you are vacationing with extended family, a gang of friends, or your besties, this new home with private beach access is a great option. The 3,000 square foot house sleeps eight and offers amazing views, cozy nesting areas, and gathering spaces.

Cape Ann’s Gorgeous Gloucester

Gorgeous Gloucester on Cape Ann’s coastline is an escape destination where your daily dilemma is which beach and which restaurant. You will love the easy, laid-back atmosphere coupled with soothing on-the-water activities and the freshest local catch.

Don’t just stop at Gloucester. See everything that Massachussetts has to offer:

• A Trip Up The Coastline Of Massachusetts: Boston To Gloucester
• 10 Best Romantic Getaways In Massachusetts
• 11 Best Apple Orchards In Massachusetts

Sandi loves writing about culture, cuisine, adult beverages, cruising, golf, skiing, road trips, hiking, New England, and photography. Traveling solo, with hubby Chris, or the entire Barrett clan there is always a story waiting to be told.

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10 Things to Do in Gloucester This November

1. Holiday shopping on Main Street A stroll down Gloucester’s Main Street is equal parts New England charm and fantastic shopping. There’s two bookstores, several boutiques, art galleries, a toy store, gourmet shops, and a few places that defy categorization (check out bakery/vintage shop/quirky home goods store Alexandra’s Bread to see what we mean). When your shopping bags are full, grab a hot beverage at the Lone Gull Coffee House or wander down a block for a sweet treat at Cake Ann.

2. Distillery tour and tasting Ryan and Wood Distillery has been distilling small-batch spirits in Gloucester since 2006. Visit their facility to view the set-up, learn more about the process, and taste selections from their line-up of gins, rums, whiskeys, and vodkas. Then grab a bottle to enjoy at home. Details and contact information available on the distillery website .

3. History and heritage at the Cape Ann Museum Focused on both art and history, the Cape Ann Museum aims to use its exhibitions to tell the story of Cape Ann. A walk through the museum offers a peek at the work of groundbreaking Folly Cove designers, a chance to immerse in Gloucester’s fishing industry, and the opportunity to wonder at the breathtaking paintings inspired by the region. Visit on Nov. 13 and you can take a walking tour of the area to see some of the houses that appear in the work of famed artist Edward Hopper.

4. Look out at Eastern Point Light At the outer tip of Gloucester’s Eastern Point, this classic New England lighthouse watches over the entrance to the country’s oldest seaport. Visitors can walk out the Dog Bar, a breakwater made from locally quarried granite that runs nearly a half mile out from the lighthouse. On one side, watch the goings on in the historic working waterfront, while on the other, views of the open ocean stretch to the horizon.

5. Bundle up on the beach The weather might be too cold for bathing suits, but a walk on the beach is delightful any time of year. Watch waves roll in at Good Harbor Beach, scramble over rocks at Wingaersheek Beach, or take in a vibrant sunset at Niles Beach. Just don’t forget your hat and scarf.

6. Hammond Castle Museum Built by radio control pioneer John Hays Hammond Jr., Hammond Castle combines elements of medieval and Renaissance architecture to create a bit of fairy tale charm in Gloucester. Visitors can wander the grounds free of charge, or pay admission to tour the eclectic interior. From mid-November on, rooms will be decorated for the holidays by local designers, so this is the ideal time of year to be charmed by the castle. Details are available at the museum website .

7. A Ravenswood ramble At Ravenswood , 10 miles of trails meander through 600 wooded acres, for a woodsy walk just moments from the sea. Studded with glacial boulders, the Ledge Hill Trail is a fun place for kids to clamber (and includes a scenic overlook of Gloucester Harbor), while the wide, largely level Old Salem Road is perfect for a low-impact stroll. Ravenswood is very dog-friendly, so bring along your canine companions.

8. Live music Gloucester’s vibrant arts scene includes a healthy population of local musicians who perform regularly at local venues. Two of your best bets are The Rhumb Line, a casual neighborhood pub that hosts rock, reggae, blues, and acoustic performers almost every night of the week, and Minglewood Harborside, a popular restaurant where you can enjoy sushi, burgers, and creative tavern food while listening to live bands.

9. Dine in an igloo When COVID shut down indoor dining and winter made outdoor seating a chilly proposition, the folks at Cape Ann Marina’s Mile Marker One restaurant got creative: They built heated plastic igloos on their deck, allowing diners to enjoy breakfast, lunch, or dinner in cozy, well-ventilated privacy. And, as of the first weekend of November, the igloos are back. Visit the marina’s website for more information, to view menus, or to make reservations.

10. Feast on seafood It would be a shame to visit the country’s oldest fishing community and not try some of its wares. And there are plenty of ways to do so. Indulge in a heaping platter of fried clams at the Causeway Restaurant , sample the lobster and cod combo at the Seaport Grille , nibble salted cod fish cakes with Portuguese spices at the Azorean Restaurant and Bar , or visit Tonno for a simple-yet-delicious meal of tuna with white beans and escarole.

Massachusetts is filled with history. Here are 10 historic places you can visit

When looking to visit a historic site , to say you're spoiled for choice in Massachusetts is an understatement. Overwhelmed would be a better word. Inundated, would be another.

With over 400 years since the first settlers made landfall in what would become Massachusetts , it's no surprise that the state has accrued its fair share of historically significant locations. A lot can happen in four centuries, in a lot of different places.

Unfortunately, most of us don't have that kind of time. For each one place visited, there are two missed out on. So how's a traveling history buff to choose? A lot of it comes down to personal preference - what time period (pre-revolutionary era, Civil War, etc.) or sites (restored houses, parks, museums) that you're looking for.

That being said, some have a reputation that proceeds them. Here are ten of the most popular historic sites to visit in Massachusetts.

North Bridge, Concord

Open daily sunrise to sunsetFree admission

Why not start our list with the site of the "shot heard around the world." The question of who fired that first shot on April 19, 1775, in the confrontation between British troops and American colonists at North Bridge has been the subject of much debate - but what can be agreed upon is it started the American Revolution. Visitors can explore the Concord Museum, which features exhibits on the American Revolution, including Paul Revere’s lantern and other artifacts from the era.

Mayflower II, Plymouth

Open daily 9 a.m. to 6 p.m.Tickets: Adult - $19, Senior - $17.10, Children - $13

No one knows for sure what happened to the original  Mayflower . The last record of the ship was an assessment of her value in 1624. After that, she disappeared from maritime records. The Mayflower II is a replica of the original (aside from a few safety updates for visitors) that brough the first settlers to Massachusetts Bay, as well as a fully functional vessel. If you ever wondered what it was like to make the crossing from England back in the 1600s, exploring this floating museum will ensure you leave with a healthy appreciation for being born in the current era.

The Old State House and Old South Meeting House, Boston

Open daily 10 a.m. to 5 p.m.Tickets: Adult - $15, Senior - $13, Children (six to 12 years old) - $8

Two buildings deeply connected to the Revolution on one ticket. The Old State House was the sight of the Boston Massacre on March 5, 1770, a key propaganda piece for the revolutionary cause (the truth is, as always, far more complicated). The Old South Meeting House was where the iconic Boston Tea Party was planned, when colonists dressed as Native Americans tossed a fortune's worth of tea into Boston Harbor in protest British taxes. Both locations have exhibits and galleries. Tours cost extra.

Walden Pond, Concord

Open daily 5 a.m. to 7:30 p.m.Parking: Resident - $8, Non-resident - $30

Yes, another Concord sight but we can't help it if the area is just so historic. Walden pond combines history and recreation in a neat, scenic package. Explore where writer and philosopher Henry David Thoreau lived (including a replica of his one-room cabin). There is also a beach, but this year, flooding has shrunk it considerably.

Lizzie Borden's House, Fall River

House tours daily 10 a.m. to 4 p.m.Tickets: House tour - $30, Ghost Tour - $25

Purported to be one of the most haunted houses in America, visitors can explore the infamous site of the double murder and even spend the night if they're feeling brave. In addition to daytime tours, after dark you can book a ghost tour as well as a ghost hunt with specialized equipment. If you want to try staying over, be sure to book well in advance.

Salem Witch Museum, Salem

Open daily, 10 a.m. to 5 p.m.Tickets: Adult - $17.50, Senior - $16, Children (six to 14 years old) - $14.50

Want to dig deep into one of the most terrifying examples of the mass hysteria in the country's history? Don't say we didn't warn you. The Salem Witch Museum examines the phenomenon that saw between 150 to 200 people jailed for witchcraft, with at least 25 people killed through looking at the historical context and the evolving perceptions of witches.

Old Sturbridge Village, Sturbridge

Open Wednesday through Sunday, 9:30 a.m. to 5 p.m.Tickets: Adults - $30, Seniors (55+) - $28, Children (four to 17) - $15

A recreation of an 1830s rural New England settlement, this living museum is filled with activities, costumed historians, and a functioning farm complete with animals. On any day you can see the blacksmith, potter, cabinetmaker, and printer at work, catch special music or storytelling performances, smell the aroma of food cooking over the hearth, learn how textiles are processed from raw materials to finished clothing.

Nantucket Whaling Museum, Nantucket

Open daily 10 a.m. to 5 p.m.Tickets: Adult - $25, Senior - $23, Youth (six to 17) - $10

Whaling was an integral part of the coastal New England economy and Nantucket was one of the primary hubs. The museum provides an insight into what life was like both on a whaling vessel and for those left behind, as well as what different parts of the whales were used for across the state and beyond.

Boston Tea Party Ships and Museum

Open daily 10 a.m. to 5 p.m.Tickets: General admission - $35

Learn about and re-enact one of the most famous tax protests in American history. A fully guided experience by costumed interpreters telling the story of that fateful night in 1773 during a tour of a replica vessel. At the end, visitors can toss boxes of tea over the side for a satisfying splash.

The House of Seven Gables, Salem

Open daily 10 a.m. to 6 p.m.Tickets: Adult - $25, Senior - $20, Children - $17

Designated a National Historic Landmark District in 2007, The House of the Seven Gables is best known today as the setting of world-renowned American author Nathaniel Hawthorne’s 1851 novel. It's also the center of a number of Salem community events.