Find The Best Things to Do in Gloucester, MA in 2025

Gloucester is one of the North Shore’s best destinations for a day on the coast. Here, you’ll find mouth-watering seafood, eye-catching scenic views, creative artistic expression, and depths and depths of history. Come make the journey to Gloucester today and discover what it’s like to be in the perfect summer destination.

Activities for the Outdoor Wanderer in Gloucester

In Gloucester, you’ll find a range of outdoor adventures perfect for the warmer or even colder months. From hiking, boating, swimming, and even skiing, you’re sure to find an outdoor adventure in Gloucester. 

Stage Fort Park

Stage Fort Park is known as the historic site of the first settlers in Gloucester in 1623. It is home to two beaches, Half Moon and Cressy Beach, and has access to a sand volleyball court, a playground, a baseball field, a basketball court, and a tennis court. 

Good Harbor Beach 

Good Harbor is one of the most well-known beaches in Gloucester with beautiful views of the ocean and lovely white sand. Swim, get your tan on, make larger-than-life sandcastles, or just relax in the warm sun. Plus, when it hits low tide, you can walk out to Salt Island, a national treasure and archipelago of granitic wooded islands. However, parking is limited, so make sure to arrive early at 8:00 am before parking spaces sell out.

Ravenswood 

Located in the Western section of Gloucester is Ravenswood Park. Here, you’ll find over 600 acres of wood, granite boulders, and carriage trails. Try out some cross-country skiing during the winter or hike the park during the warmer months to explore bursts of color surrounding the trails. 

Cape Ann Whale Watch 

Get a front-row seat for whale-watching with Gloucester’s own Cape Ann Whale Watch. You will go aboard Hurricane II, the largest and fastest whale watch vessel North of Boston, and travel to the National Marine Statuary Stellwagen Bank to see and learn more about whales. The Cape Ann Whale Watch runs from April 27th until November 3rd and trips are up to three or four hours long. 

Eastern Point Light and Ten Pound Light

Right in Gloucester, MA you’ll find the Eastern Point Light and Ten Pound Light. These two lighthouses began as guides for ships on the water. At the entrance of Gloucester Harbor sits the DogBar Breakwater, a granite jetty where you can walk to the end and enjoy the views of Gloucester Harbor and the Boston skyline. While the actual lighthouse is closed to the public, you can visit the breakwater right next to it. 

Ten Pound Island Light is an artist’s treasure, as American artist Winslow Homer produced around 50 paintings of Gloucester Harbor and the lighthouse. This lighthouse is closed to the public but you can view it by boat or from the Gloucester Waterfront. 

Find more places for outdoor adventure North of Boston.

Get a Taste of History at Museums in Gloucester

As one of the oldest seaports in the United States, Gloucester is home to museums and attractions that are integral to its culture and history. Discover the city’s maritime history and its thriving artist culture. 

Hammond Castle Museum

Hammond Castle Museum was formerly the home and laboratory of inventor John Hays Hammond Jr. and housed his private artifact collection from ancient Rome through the Renaissance. The museum offers guided and self-guided tours from April until December to explore the castle’s architecture and European artifacts.  

Maritime Gloucester

Fun for the whole family, Maritime Gloucester is located on the harbor and is the place to learn more about the coastal city’s rich heritage. Here, you can visit the Gorton’s Seafood Gallery to explore the area’s enduring maritime legacy and the Maritime Science Education Center which includes a seasonal Seapocket aquarium perfect for kids of all ages.

Beauport, the Sleeper McCann House

Beauport, the Sleeper-McCann House is a National Historic Landmark and the summer home of Henry Davis, one of America’s first professional interior designers. Schedule a tour between late May and October 15th, and discover a collection of period furniture, glassware, books, ceramics, hooked rugs, silhouettes, and curiosities within the many rooms.  

Find more places to get in touch with history North of Boston.

Satisfy Your Cravings with Restaurants in Gloucester

Because Gloucester is located right on the water, many local restaurants get their ingredients right from the city’s fishing port. When you visit any restaurant here, you’ll get the chance to eat some of the freshest seafood. Take a break from all the outdoor adventure and sightseeing and eat at one of Gloucester’s fabulous restaurants.

Seaport Grille

Enjoy Gloucester’s Surf n’ Turf dining experience at Seaport Grille. Their menu includes a wide range of cuisines made with the freshest ingredients which include seafood, classic American plates, Italian-inspired dishes, and world-famous desserts. Plus, try out the waterfront dining deck with excellent views of Gloucester Harbor. It’s also heated so you can enjoy it even during colder seasons! 

Mile Marker One Waterfront Restaurant

Another restaurant on the waterfront is the Mile Marker One Waterfront Restaurant. Here, you’ll find seafood favorites such as lobster, oysters, tuna, scallops, clams, and a twist on a classic with the Haddock Reuben. Choose to dine inside or outside with picturesque views of the Annisquam River. In the wintertime, you can dine inside a heated Igloo. 

Nichol’s Candy

For a little sweet treat, order some candy at Gloucester’s oldest candy shop Nicholas Candies. Opened in 1932, this shop sells an assortment of candies from brittle candies, caramels, clusters, fresh roasted nuts, mints, fudge, penuche, and so much more.  

Find more places to enjoy delicious food North of Boston

Music and Art Come Alive in Gloucester

Theater, music, and art thrive in Gloucester. Whether you’re interested in the dramatic arts or want to journey through artist goldmines, you’ll find plenty to explore. Here are some of the special music and artist venues located within Gloucester.   

Gloucester Stage Co.

See a show in a century-old brick warehouse at the professional non-profit theater company Gloucester Stage Company. Catch a contemporary play or an exciting classic that has started on this stage and made its move to New York and Paris. The theater is even home to intimate concerts where you can watch musicians and singers perform covers of some of music’s best performers. 

Rocky Neck Art Colony

Escape into a world of artistry with Gloucester’s Rocky Neck Art Colony. Working artists like painters, potters, textile designers, photographers, and jewelry makers display their work in galleries along Rocky Neck. The colony is open from Thursday to Sunday and each year brings new and returning artists. 

Find out more about art all around North of Boston.  

Find Treasures at Shops in Gloucester

This coastal city is home to many unique gems, especially with its strong connection to physical art. Get your next pair of shoes, clothes, or a story to read at the various shops in Gloucester.  

Mark Adrian Shoes

This long-running and family-operated shoe store offers customers shoes fit for walking, hiking, school sports, leisure, or even a special night on the town. The emphasis is always on quality and style, as the store offers brands like Merrell, Keen, Clarks, Birkenstocks, Dansko, and others. Plus, the store is open year-round, seven days a week!

Second Glance Thrift Store

Second Glance Thrift Store has a changing inventory that includes clothing, jewelry, housewares, furniture, books, games, and music. And when you buy from this thrift store, you’re giving back to the community, as proceeds support local hunger relief programs that are available through The Open Door.  

The Bookstore of Gloucester

The Bookstore of Gloucester has been entertaining audiences for nearly 50 years. With humble beginnings, Ann Banks, her son, and Harold Bell opened the store in 1975, offering hand-picked books in a variety of genres. 

Find more shopping opportunities North of Boston.

Places to Rest Your Head in Gloucester

Sometimes you need more than one day to enjoy the beauty of Gloucester. Extend your trip to and unwind at one of the city’s inns or hotels. 

Harborview Inn Gloucester

The Harborview Inn lives on America’s oldest harbor in Gloucester. Within this inn, you’ll find historical paintings, bright fresh, paint colors, and nautical elements around every corner. This inn is within walking distance away from beaches, galleries, shops, restaurants, and the famous Gloucester Fisherman’s Memorial Statue.  

Beauport Hotel Gloucester

What can be better than a hotel right on the beach?! The Beauport Hotel Gloucester sits on America’s oldest fishing port and offers spacious coastal elegance, upscale amenities, and unforgettable hospitality. 

The Hotel at Cape Ann Marina

This waterfront property is a hotel, restaurant, and marina providing picturesque views, waterfront venues, and exquisite dining options. Here, you’ll have an all-in-one destination and enjoy both relaxation and adventure. Gloucester’s Mile Marker One restaurant is located right at the hotel. 

Find more places to stay North of Boston.

Get ready for adventure the moment you step into the city of Gloucester. If you’d like to explore more of what North of Boston has to offer, check out things to do in Cape Ann and Rockport.