Top 21 Best Things to Do in Gloucester Massachusetts

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.

An aerial view of Gloucester Massachusetts

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

Gloucester MA harbor with American flags along the border

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

The inside of 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

An aerial photo of Cape Ann. Driving along the coast is one of the things to do in Gloucester MA

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

An aerial view of Good Harbor Beach in Gloucester MA

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

A view of 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

A whale breaching the water off the shore of Gloucester Massachusetts

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:

Stroll through Stage Fort Park

Stage Fort Park - among the things to do in Gloucester MA

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

A restaurant sign in Gloucester Massachusetts

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

A view of the Eastern Point Lighthouse - among the things to do in Gloucester MA

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

The woods of 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

The Annisquam River - among the things to do in Gloucester MA

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

A schooner of the Gloucester shore

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

An umbrella with lights

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

The Sargent House Museum
Photo credit: Doug Kerr / Creative Commons

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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A photo of Kerry Flatley leaning against a wall

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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