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30 Things to Do in Gloucester, Massachusetts (MA)

Gloucester, Massachusetts, located on the picturesque Cape Ann in the northeastern part of the state, is a historic seaport that attracts visitors with its rich maritime heritage, scenic beauty, and vibrant arts scene. Whether you're an adventure seeker, a history enthusiast, or an art lover, Gloucester offers a variety of attractions and activities that cater to every taste.

Unique Facts About Gloucester

America's Oldest Seaport

Established in 1623, Gloucester is one of the oldest and most important fishing ports in the United States. This long history of maritime activities has shaped much of the city's identity, and it remains a hub for the fishing industry to this day.

Artistic Legacy

Gloucester is home to the Rocky Neck Art Colony, the oldest working art colony in America. The city has served as an inspiration for renowned artists like Winslow Homer and Edward Hopper. Its stunning coastal landscapes and historic charm have drawn artists for generations, making it a perfect addition to your list of things to do in Newburyport, Massachusetts (MA).

Maritime Traditions

Gloucester’s fishing heritage is celebrated every year at the St. Peter's Fiesta. This lively festival includes traditional events such as the Greasy Pole contest, where contestants try to walk across a wooden pole above the harbor. If you're looking for more activities, check out the exciting things to do in Cambridge, Massachusetts (MA), which offer a rich blend of history, culture, and unique experiences.

Infographic - 30 Things to Do in Gloucester, Massachusetts (MA)

30 Things to Do in Gloucester, Massachusetts (MA)

Gloucester, located on the scenic coast of Massachusetts, is known for its rich maritime history, stunning beaches, and vibrant arts scene. Whether you're a beach lover, history buff, or art enthusiast, Gloucester offers a variety of activities that cater to every interest. Here’s a guide to the top things to do in this charming coastal town.

1. Relax at Good Harbor Beach

Short Description of Activity
Good Harbor Beach is one of Gloucester’s most popular beaches, offering soft sands, clear waters, and stunning views of the Atlantic Ocean. It’s the perfect spot to relax, sunbathe, or take a refreshing swim.

Pros and Cons
Pros:

  • Beautiful, clean beach with great views

  • Less crowded during off-peak hours

  • Family-friendly with gentle waves for swimming

Cons:

  • Can get crowded during peak summer months

  • Parking can be difficult to find during weekends in high season

Key Attractions and Events:

  • Sunset views over the Atlantic

  • Annual sandcastle competition in the summer

2. Visit Wingaersheek Beach

Short Description of Activity
Wingaersheek Beach is another stunning beach in Gloucester, known for its calm waters and scenic beauty. The beach is perfect for families and offers a great place for a day of relaxation or a peaceful walk along the shore.

Pros and Cons
Pros:

  • Calm and shallow waters, ideal for children

  • Less crowded compared to Good Harbor Beach

Cons:

  • Limited amenities, so bring your own food and drinks

  • Can have limited parking spaces

Key Attractions and Events:

  • Ideal for kayaking and paddleboarding

  • Great place to spot local wildlife, such as seals

3. Tour Hammond Castle Museum

Short Description of Activity
Step back in time by visiting the Hammond Castle Museum. Located on the beautiful Gloucester coastline, this medieval-style castle offers a unique blend of history and architecture.

Pros and Cons
Pros:

  • Fascinating history and architecture

  • Gorgeous ocean views from the castle

Cons:

  • Admission fee required

  • Some areas of the castle can be hard to access for those with mobility issues

Key Attractions and Events:

  • Year-round guided tours

  • Special events like medieval festivals

4. Go Whale Watching

Short Description of Activity
Gloucester is one of the best spots for whale watching on the East Coast. Take a boat tour from the harbor to spot humpback, finback, and minke whales, along with other marine wildlife.

Pros and Cons
Pros:

  • Incredible opportunity to see whales up close

  • Experienced guides provide insightful commentary

Cons:

  • Tours can be pricey

  • Weather conditions may affect tours

Key Attractions and Events:

  • Best whale watching months are from April to October

  • Special tours focused on other marine life, including dolphins

5. Walk the Gloucester HarborWalk

Short Description of Activity
The Gloucester HarborWalk is a scenic waterfront trail that winds around the city’s historic harbor. It’s perfect for a leisurely walk while enjoying stunning views of the harbor and local ships.

Pros and Cons
Pros:

  • Free and open to everyone

  • Great for sightseeing and photography

Cons:

  • Can be crowded during peak tourist season

  • The walk can be long for those not used to walking

Key Attractions and Events:

  • Waterfront views and historic ships

  • Access to various seafood restaurants along the way

6. Explore Rocky Neck Art Colony

Short Description of Activity
Rocky Neck Art Colony is a renowned area in Gloucester where artists create and exhibit their work. It’s a vibrant hub of creativity, offering galleries, workshops, and stunning views of the harbor.

Pros and Cons
Pros:

  • Offers a glimpse into the local art scene

  • Beautiful views of the harbor

Cons:

  • Some galleries may be closed during off-peak seasons

  • Not all galleries are free to enter

Key Attractions and Events:

  • Regular art exhibitions

  • Annual Rocky Neck Art Colony Open House

7. Visit the Cape Ann Museum

Short Description of Activity
The Cape Ann Museum celebrates the history, art, and culture of Gloucester and its surrounding areas. This museum houses impressive collections of local artwork, maritime history, and cultural exhibits.

Pros and Cons
Pros:

  • Insightful exhibits about Gloucester’s maritime history

  • Great for history and art enthusiasts

Cons:

  • Small museum, may not take more than a few hours to explore

  • Admission fee

Key Attractions and Events:

  • Art exhibitions focusing on local painters and sculptors

  • Annual cultural events

8. Stroll Downtown Gloucester

Short Description of Activity
Take a stroll through Gloucester's charming downtown area, filled with local shops, restaurants, and historical landmarks. The area offers an authentic New England experience with its cobblestone streets and cozy ambiance.

Pros and Cons
Pros:

  • Great for shopping and dining

  • Quaint, historic atmosphere

Cons:

  • Limited parking

  • Some shops may be closed on Sundays

Key Attractions and Events:

  • Local art galleries and artisan shops

  • Annual arts and food festivals

9. See the Gloucester Fishermen’s Memorial

Short Description of Activity
The Gloucester Fishermen’s Memorial is a tribute to the brave fishermen who lost their lives at sea. It’s an emotional and respectful spot to honor the local fishing community.

Pros and Cons
Pros:

  • Moving and meaningful historical landmark

  • Beautiful views of the waterfront

Cons:

  • May not be of interest to all visitors

  • Limited amenities nearby

Key Attractions and Events:

  • Memorial services held on significant dates

  • Located near other historic sites

10. Take a Schooner Sail on the Thomas E. Lannon

Short Description of Activity
The Thomas E. Lannon is a classic wooden schooner that offers scenic sailing tours around the harbor. It’s a great way to see Gloucester from the water while learning about its maritime history.

Pros and Cons
Pros:

  • Unique, historical sailing experience

  • Beautiful views of the harbor and coastline

Cons:

  • Limited seating and availability during peak seasons

  • Requires booking in advance

Key Attractions and Events:

  • Sunset sailing tours

  • Educational tours on Gloucester’s maritime history

11. Hike in Ravenswood Park

Short Description:
Ravenswood Park is a peaceful natural reserve known for its extensive network of trails. Located just outside the city, it offers a serene escape where you can explore lush forests, tranquil ponds, and rolling hills.

Pros and Cons:

Pros:

  • Beautiful forested trails

  • Peaceful and quiet environment

  • Perfect for birdwatching and photography

Cons:

  • Some trails can be muddy after rainfall

  • Limited signage on certain routes

Key Attractions and Events:

  • The park offers an annual nature walk led by park rangers

  • Several scenic spots perfect for a peaceful picnic

12. Tour the Beauport Sleeper-McCann House

Short Description:
The Beauport Sleeper-McCann House, also known as Beauport, is a historic mansion overlooking Gloucester Harbor. It was once the home of designer Henry Sleeper and is now a museum showcasing early 20th-century decorative arts.

Pros and Cons:

Pros:

  • Beautiful historical architecture

  • Great views of the harbor

  • Rich in history and design

Cons:

  • Admission fee required

  • Limited hours of operation

Key Attractions and Events:

  • Guided tours available to learn about the history and design of the house

  • Special events like lectures and seasonal exhibitions

13. Attend the St. Peter’s Fiesta

Short Description:
The St. Peter’s Fiesta is one of Gloucester's biggest and most beloved celebrations, held annually in honor of the city’s patron saint. It’s a lively event featuring traditional Italian-American food, music, games, and a colorful parade.

Pros and Cons:

Pros:

  • A true local cultural experience

  • Fun for all ages with games, food, and entertainment

  • The parade is vibrant and full of energy

Cons:

  • Can get crowded, especially on weekends

  • Parking may be difficult to find during peak times

Key Attractions and Events:

  • The famous Greasy Pole contest

  • The parade featuring local bands and floats

14. Explore Dogtown Common

Short Description:
Dogtown Common is a fascinating historical site filled with old stone walls, rock carvings, and an intriguing past. It’s a great spot for hiking, photography, and discovering the town’s early history.

Pros and Cons:

Pros:

  • Unique historical significance

  • Great for hiking and outdoor exploration

  • Beautiful natural landscapes

Cons:

  • Some trails are difficult to navigate

  • The site may feel isolated for those seeking more amenities

Key Attractions and Events:

  • Old stone carvings left by early settlers

  • Annual guided historical tours of the area

15. Visit Eastern Point Lighthouse

Short Description:
Eastern Point Lighthouse is one of Gloucester’s most iconic landmarks. It’s located at the entrance of Gloucester Harbor and offers a picturesque view of the coastline and the ocean beyond.

Pros and Cons:

Pros:

  • Breathtaking views of the harbor and ocean

  • A historic lighthouse still in operation

  • Perfect spot for photography

Cons:

  • The lighthouse is not always open to the public

  • The area can be windy and cold, even in summer

Key Attractions and Events:

  • The lighthouse itself, offering a glimpse into maritime history

  • A great spot to watch boats and ships pass by

16. Stop by Stage Fort Park

Short Description:
Stage Fort Park is a beautiful waterfront park that has something for everyone. Whether you’re looking for a place to relax by the water, play sports, or explore local history, Stage Fort Park is the ideal spot.

Pros and Cons:

Pros:

  • Gorgeous waterfront views

  • Family-friendly with playgrounds and picnic areas

  • Historic significance with landmarks like the Fishermen’s Memorial

Cons:

  • Can be crowded during peak tourist seasons

  • Some areas may require a small parking fee

Key Attractions and Events:

  • Fishermen’s Memorial statue

  • Annual outdoor concerts and family-friendly events

17. Enjoy the Gloucester Schooner Festival

Short Description:
The Gloucester Schooner Festival is a maritime celebration showcasing beautiful tall ships and schooners. This event features races, tours, and various nautical-themed activities that highlight the area’s rich seafaring tradition.

Pros and Cons:

Pros:

  • Beautiful views of historic sailing ships

  • Educational for those interested in maritime history

  • Fun activities like boat tours and races

Cons:

  • Admission fees for some activities

  • Large crowds during events

Key Attractions and Events:

  • Schooner races in Gloucester Harbor

  • Public tours of the historic ships

18. Eat Fresh Seafood at The Causeway

Short Description:
For a quintessential Gloucester experience, The Causeway offers some of the freshest seafood around. Located near the water, it serves up lobster rolls, clam chowder, and other local specialties.

Pros and Cons:

Pros:

  • Fresh, high-quality seafood

  • Great local atmosphere with scenic views

  • Friendly, casual dining experience

Cons:

  • Can be expensive, especially for seafood dishes

  • Limited indoor seating during busy times

Key Attractions and Events:

  • Fresh seafood specials, including lobster rolls and fried clams

  • Local music performances in the warmer months

19. Paddleboard or Kayak the Harbor

Short Description:
Gloucester Harbor is the perfect spot for paddling adventures, offering calm waters and stunning views of the coastline. Whether you're into kayaking or paddleboarding, this is a fantastic way to experience Gloucester from the water.

Pros and Cons:

Pros:

  • Calm and scenic waters for beginners

  • Great exercise and fun for groups or solo adventurers

  • Incredible views of the city and its harborside attractions

Cons:

  • Rentals can be pricey during peak season

  • Not suitable for those unfamiliar with water sports

Key Attractions and Events:

  • Guided kayaking tours of the harbor

  • Sunset paddling excursions

20. Take a Sunset Cruise

Short Description:
For a truly magical experience, take a sunset cruise around Gloucester Harbor. This scenic boat ride offers panoramic views of the coastline as the sun sets behind the horizon, providing the perfect end to a day of exploration.

Pros and Cons:

Pros:

  • Gorgeous views of the harbor and coastline

  • A relaxing and romantic experience

  • Excellent opportunity for photography

Cons:

  • Cruises can be expensive, especially during peak season

  • Limited availability depending on the time of year

Key Attractions and Events:

  • Sunset cruises that highlight the beauty of Gloucester’s coastline

  • Opportunities to see local wildlife, including seals and seabirds

21. Snap Photos at Bass Rocks

Short Description:
Bass Rocks is one of the most iconic spots in Gloucester, known for its dramatic coastal views. It’s perfect for photography, offering breathtaking views of the Atlantic Ocean, rock formations, and lighthouses.

Pros:

  • Stunning coastal views.

  • Great for photography enthusiasts.

  • Peaceful and serene atmosphere.

Cons:

  • Limited facilities or services in the area.

  • Can be crowded during peak tourist seasons.

Key Attractions and Events:

  • Incredible ocean views.

  • Ideal for nature photography.

  • Close proximity to the Eastern Point Lighthouse.

22. Check Out the Fishermen’s Wives Memorial

Short Description:
The Fishermen’s Wives Memorial is a poignant tribute to the wives and families of Gloucester’s fishermen, many of whom risked their lives at sea. The memorial is a must-see for those interested in the town's maritime heritage.

Pros:

  • Rich in history and emotion.

  • A great spot for reflection.

  • Educational for visitors interested in maritime history.

Cons:

  • Limited interaction or activities beyond viewing the memorial.

  • Small area, may be hard to explore if busy.

Key Attractions and Events:

  • Memorial sculpture honoring the wives of Gloucester's fishermen.

  • Insight into Gloucester's historical dependence on fishing.

23. Have a Beer at Cape Ann Brewing Co.

Short Description:
Cape Ann Brewing Co. is one of the best places to grab a locally brewed beer in Gloucester. Known for its craft beers and welcoming atmosphere, it’s a great spot for beer lovers to relax.

Pros:

  • Local craft beer selection.

  • Comfortable and casual environment.

  • Great place for socializing.

Cons:

  • May not have a wide variety of non-alcoholic options.

  • Can be busy during peak hours.

Key Attractions and Events:

  • Frequent beer tastings and events.

  • Seasonal beer releases.

  • Live music and food trucks.

24. Attend the Waterfront Festival

Short Description:
The Waterfront Festival is a popular annual event that celebrates Gloucester’s maritime culture. It features food, live music, and maritime-themed activities, making it a fun and lively event for all ages.

Pros:

  • Family-friendly event.

  • Diverse activities and entertainment.

  • Great food and local craft vendors.

Cons:

  • Can get overcrowded during peak times.

  • Events and performances are weather-dependent.

Key Attractions and Events:

  • Live music performances.

  • Seafood tastings and food vendors.

  • Boat tours and maritime-related activities.

25. Walk the Breakwater to the Lighthouse

Short Description:
The Breakwater offers a scenic walk that leads visitors to the Eastern Point Lighthouse. It’s a perfect activity for those looking to enjoy stunning ocean views while exploring the rugged coastline.

Pros:

  • Amazing views of the ocean and coastline.

  • Peaceful and calming experience.

  • Great for fitness enthusiasts.

Cons:

  • Can be a bit challenging due to rocky paths.

  • Limited shelter if the weather turns bad.

Key Attractions and Events:

  • Eastern Point Lighthouse at the end of the walk.

  • Beautiful seascapes along the way.

  • Opportunity for bird watching.

26. Visit the Sargent House Museum

Short Description:
The Sargent House Museum is a historical site showcasing the life and legacy of Sarah Elizabeth Sargent. This museum offers insights into the town’s history and the prominent figures who helped shape it.

Pros:

  • Fascinating historical exhibits.

  • Beautiful architecture.

  • Quiet and educational environment.

Cons:

  • Limited accessibility for those with mobility issues.

  • Can be small if you're expecting a larger museum experience.

Key Attractions and Events:

  • Period furniture and artifacts from the 18th century.

  • Educational programs on Gloucester's history.

  • Beautifully preserved historical building.

27. Browse the Gloucester Farmers Market

Short Description:
The Gloucester Farmers Market is the ideal place to pick up fresh produce, local goods, and handmade crafts. It's an excellent spot to support local vendors and enjoy the town's agricultural offerings.

Pros:

  • Fresh, local produce and goods.

  • Great atmosphere for local shopping.

  • A fun way to experience the local culture.

Cons:

  • Limited to certain days and hours.

  • Can be crowded on weekends.

Key Attractions and Events:

  • Weekly vendor stalls with fresh produce.

  • Local artisans and craft vendors.

  • Live entertainment and food trucks.

28. Fish Off the Pier or Join a Charter

Short Description:
Fishing is a central activity in Gloucester, and whether you’re casting a line from the pier or taking a charter boat out into the Atlantic, you can experience the town’s vibrant fishing culture firsthand.

Pros:

  • Perfect for fishing enthusiasts.

  • Chance to catch local fish.

  • Charter boats offer an immersive fishing experience.

Cons:

  • Weather-dependent activity.

  • Can be expensive for charter tours.

Key Attractions and Events:

  • Charter tours for deep-sea fishing.

  • Pier fishing with a variety of catches.

  • Annual fishing competitions.

29. Check Out the Maritime Heritage Center

Short Description:
The Maritime Heritage Center is an interactive museum where visitors can learn about Gloucester’s rich maritime history, from the fishing industry to shipbuilding and the town’s role in the American Revolution.

Pros:

  • Rich in maritime history.

  • Interactive exhibits.

  • Educational for all ages.

Cons:

  • Small venue, may not take long to explore.

  • Limited outdoor activities associated with the center.

Key Attractions and Events:

  • Exhibits on Gloucester’s maritime history.

  • Artifacts from Gloucester’s fishing industry.

  • Educational programs and guided tours.

30. Explore Annisquam Village

Short Description:
Annisquam Village is a charming and historic neighborhood that provides a tranquil escape from the bustle of Gloucester. Known for its historic homes and peaceful ambiance, it’s an excellent place for a leisurely stroll.

Pros:

  • Quaint and picturesque setting.

  • Peaceful, relaxing atmosphere.

  • Ideal for photography and exploration.

Cons:

  • Limited commercial amenities.

  • May feel isolated compared to the more bustling parts of Gloucester.

Key Attractions and Events:

  • Historic homes and architecture.

  • Gorgeous waterfront views.

  • Quiet, scenic walking paths.

Best Time to Visit Gloucester

Gloucester offers something unique during every season, making it an ideal year-round destination. Here's a breakdown of what to expect during each season:

Season Months Highlights
Spring March to May Whale watching begins; mild temperatures perfect for outdoor activities.
Summer June to August Beaches at their best; St. Peter’s Fiesta and other local festivals.
Fall September to November Crisp air and foliage; fewer crowds; ideal for hiking and exploring historical sites.
Winter December to February Tranquil off-season; opportunities for winter sports in nearby areas.

Unique Gems of Gloucester

Hammond Castle Museum

Step back in time with a visit to Hammond Castle, a medieval-style structure built in the 1920s. It’s home to an extensive collection of artifacts and offers guided tours that give insight into the castle's fascinating history.

Cape Ann Museum

For those interested in art and history, the Cape Ann Museum is a must-visit. The museum features works from the Cape Ann Art Colony, along with exhibits dedicated to the area's fishing and maritime traditions.

Rocky Neck Art Colony

Take a leisurely stroll through the historic Rocky Neck Art Colony. This vibrant community of artists, which dates back to the 1850s, is the perfect place to explore galleries and studios while enjoying stunning harbor views.

Sample Day Itinerary in Gloucester

Morning:

  • Visit Good Harbor Beach: Start your day with a relaxing walk on one of Gloucester’s most popular beaches. Known for its soft white sand and scenic views, Good Harbor Beach offers a perfect spot to unwind.

Afternoon:

  • Explore Hammond Castle Museum: After a morning at the beach, head to Hammond Castle Museum. The architecture and expansive collection of artifacts make it a fascinating stop.

  • Lunch at a Local Seafood Restaurant: Gloucester is known for its fresh seafood. Enjoy a delicious meal at a local restaurant like The Lobster Pool, which serves up some of the best seafood in the area.

Evening:

  • Stroll Through Rocky Neck: In the evening, take a stroll through the historic Rocky Neck Art Colony. Explore galleries and studios, and enjoy the beautiful harbor views.

  • Dinner at a Waterfront Eatery: End your day with dinner at one of Gloucester’s waterfront eateries. Dine while watching the sunset over the harbor and savor the freshest seafood the city has to offer.

How to Reach Gloucester, Massachusetts

By Car

Gloucester is located approximately 45 minutes northeast of Boston via Route 128. It’s a scenic drive that takes you through the Massachusetts countryside, making the journey just as enjoyable as the destination.

By Train

The MBTA’s Newburyport/Rockport line connects Boston’s North Station to Gloucester. The train ride offers a comfortable and convenient way to reach the city, and the station is located downtown, making it easy to explore the area.

By Bus

If you prefer to travel by bus, there are several services available, including the Cape Ann Transportation Authority (CATA), which offers routes to and from Gloucester.

Conclusion

Gloucester, Massachusetts, seamlessly blends its historical significance with cultural richness and natural beauty. Whether you’re exploring its maritime history, indulging in delicious seafood, or immersing yourself in its thriving art scene, Gloucester promises a memorable experience for every traveler. The city's unique combination of old-world charm and modern attractions ensures that there’s something for everyone. Similarly, things to do in Burlington, Massachusetts (MA) offer a delightful mix of history, nature, and modern amenities for all types of visitors.

Frequently Asked Questions (FAQs)

What are the must-visit beaches in Gloucester?

Good Harbor Beach and Wingaersheek Beach are the top beaches in Gloucester. Both offer pristine sand and stunning views, making them perfect spots for relaxation and recreation.

When is the best time to experience Gloucester's festivals?

Late June is an excellent time to visit if you want to experience the vibrant St. Peter’s Fiesta, a celebration of Gloucester’s fishing heritage. This event features fun activities like the Greasy Pole contest.

Are there family-friendly activities in Gloucester?

Absolutely! Gloucester offers plenty of family-friendly activities such as visiting the beaches, exploring interactive museum exhibits, and enjoying scenic parks.

How can I explore Gloucester's art scene?

To experience Gloucester’s artistic heritage, visit the Rocky Neck Art Colony and the Cape Ann Museum. Both venues showcase the city’s rich artistic legacy and are must-see attractions for art lovers.

Is Gloucester accessible for travelers with mobility challenges?

While many of Gloucester’s outdoor attractions are accessible, it’s always best to check specific venues for detailed accessibility features to ensure a smooth visit.

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