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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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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 best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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:

The best things to do in Gloucester Massachusetts

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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