Things To Do In Gloucester, MA

Founded in 1623, Gloucester, MA is America’s oldest seaport, and has maintained an active harbor and fishing industry for over 400 years. Gloucester’s long-standing working relationship with the sea has percolated into its culture, mixing with the city’s historical coastal Italian, Scandinavian, and Brazilian influences. From its vibrant downtown to its beautiful and rugged landscape, you will never run out of things to do in Gloucester.

THINGS TO DO IN GLOUCESTER MA

Gloucester consists of a number of different neighborhoods (see map below), each with their own distinct features, history, and personality. By crossing over the large A. Piatt Andrew Bridge, you officially enter Gloucester’s “island” section, which, with the exception of Wingaersheek and a few other beaches, is where most of Gloucester’s primary attractions reside. Downtown Gloucester features a number of delicious local restaurants, a myriad of bustling small businesses, and a large variety of historic and scenic points of attraction. For night owls, Gloucester has a thriving nightlife, and is home to a number of bars, taverns, and a movie theater featuring the latest releases.

Gloucester’s most iconic cultural event is St. Peter’s Fiesta, a 5-day festival put on by Gloucester’s Italian-American community. Events include a carnival, the Greasy Pole contest, Seine Boat races, and parades, as well as the Blessing of the Fleet Mass at the festival’s conclusion.

Gloucester is also well-known for whale watching and there are several companies that provide daily trips to Stellwagen Bank, Jefferys Ledge, and other popular whale feeding grounds. Whale watch excursions fill up quickly in the summer months, so advance reservations are usually recommended.

Fishing charters and schooner sails are other ocean-based activities that draw visitors from all areas of the globe. The schooners Thomas E. Lannon, the Ardelle and the Adventure offer tours and sails throughout the summer. Gloucester’s annual Schooner Festival is traditionally held over Labor Day Weekend and features cultural events, a prestigious schooner race (The Mayor’s Race), a Boat Parade of Lights, fireworks and more.

For those looking to learn all they can about this historic city, Gloucester HarborWalk lets you experience Gloucester in a personal, relaxed, and scenic manner. Gloucester HarborWalk is a free, public access walkway with an accompanying self-guided walking tour. Designated by 42 granite story posts integrated into the city, the tour directs you to gardens, art galleries, spectacular views of Gloucester’s working harbor, and more.

Fishing charters and schooner sails are other ocean-based activities that draw visitors from all areas of the globe. The schooners Thomas E. Lannon, the Ardelle and the Adventure offer tours and sails throughout the summer. Gloucester’s annual Schooner Festival is traditionally held over Labor Day Weekend and features cultural events, a prestigious schooner race (The Mayor’s Race), a Boat Parade of Lights, fireworks and more.

For those looking to learn all they can about this historic city, Gloucester HarborWalk lets you experience Gloucester in a personal, relaxed, and scenic manner. Gloucester HarborWalk is a free, public access walkway with an accompanying self-guided walking tour. Designated by 42 granite story posts integrated into the city, the tour directs you to gardens, art galleries, spectacular views of Gloucester’s working harbor, and more.

Gloucester restaurants are known for their fresh-off-the-boat seafood that cannot be matched. Even if seafood is not what you’re after, there are many other cuisine options to choose from. After eating, walk around downtown or along Stacy Boulevard, which parallels the Atlantic coastline and provides easy, scenic access to Stage Fort Park. 

Walking the length of the half-mile promenade, you’ll pass Gloucester’s iconic Fisherman’s Monument (also known as the “Man at the Wheel”) and cenotaph, as well as the Fisherman’s Wives Memorial statue. 

For those interested in art, local history and/or maritime history, there are several Gloucester activities that will appeal. Maritime Gloucester offers exhibits on Gloucester’s maritime heritage, marine science, and environmental stewardship. Their small “Pocket Aquarium,” featuring starfish, lobsters, and other local specimens that visitors can see and touch.

The Cape Ann Museum has outstanding collections of local art, furniture, textiles and artifacts that reflect the area’s history and culture. Gloucester’s land and seascapes have long been an inspiration artists such as Fitz Henry Lane, Winslow Homer, Emile Gruppe and others. Artists and art lovers will also want to make a trip the Rocky Neck Art Colony, which is one of the oldest working art colonies in the country. Rocky Neck is home to dozens of working artists and their galleries, featuring works of all types, including paintings, photography, jewelry, prints, sculpture, and ceramics.

Gloucester also boats several historical homes of note. One of the most famous is Hammond Castle, built in a medieval-style by John Hays Hammond, Jr.  Hammond Castle now offers daily tours in the summer, allowing visitors to view its abundant furnishings, artwork and collections of artifacts. Beauport, also knows as the Sleeper-McCann House, was built as a summer home by the interior decorator and antique collector Henry Davis Sleeper. The home has many intricate architectural details and design elements and also contains a rich collection of folk art and original furnishings. The Sargent House is a Georgian-era mansion that was home to Gloucester sea merchants and community leaders. Guided tours take visitors past a fine collection of American decorative arts and furniture. 

GLOUCESTER MA BEACHES

Gloucester boasts some of the best beaches in Massachusetts; they draw in visitors not just from New England, but from all over the world. Gloucester’s Atlantic-facing Good Harbor Beach has great waves and plenty to discover. At low tide you can walk out to nearby Salt Island for great views of the beach and a whole new area to explore. 

Wingaersheek Beach’s large size, calm waters, and protected dunes have made it incredibly popular across every age group. At low tide, the beach extends out for hundreds of yards, making it perfect for a walk with your loved ones. At high tide, the water fills up small tidal pools scattered along the beach that are perfect for small children to splash in. Good Harbor, along with Wingaersheek, are two of the most popular beaches in Massachusetts.

Plum Cove Beach is a small neighborhood beach in Lanesville, in the northern section of Gloucester. Plum Cove Beach is a favorite with families, as its smaller size makes it easier to keep an eye on little ones.

Cressey Beach and Half Moon Beach are both found at Stage Fort Park, with Pavilion Beach located at the other end of Stacy Boulevard, just past Saint Peter’s Square.

Niles Beach in East Gloucester is another small neighborhood beach, adjacent to the historical mansions of Eastern Point. On clear days, the Boston skyline is visible from the beach. 

GLOUCESTER MA PARKS & TRAILS 

Gloucester is a nature lover’s paradise, with 2 Trustees-managed reservations, over 40 Greenbelt-protected areas, Dogtown Common (one of New England’s most famous abandoned settlements), multiple beaches, and a number of swimmable quarries. 

If you enjoy kayaking, try launching either from various points on the Annisquam River or from Lanesville’s Lanes Cove or nearby Gloucester Harbor. The Lanes Cove area is full of beautiful sights and scenic areas to explore, and paddling from Gloucester Harbor to the nearby historic Ten Pound Island is a popular activity. Hiking enthusiasts have their pick of Gloucester’s innumerable walking trails, including the many trails located in popular Ravenswood Park, Dogtown Common, and Goose Cove Reservation. Mountain bikers as well as hikers from all over the North Shore love the winding, hilly trails and man-made features in the Tompson Street Reservation.

Looking for things to do in Gloucester MA on a budget? Check out our blog post, 25 Free Things To Do On And Around Cape Ann This Summer.