The 10 Best Things to Do in Gloucester, Massachusetts

See the Gloucester Fisherman's Memorial

It's estimated that 10,000 Gloucester fishermen have died at sea. Those lost lives are commemorated by the Gloucester Fisherman's Memorial, commonly known as "The Man at the Wheel." Commissioned in 1923 during Gloucester's 300th-anniversary commemoration, the monument has since become the city's iconic symbol. The 8-foot-tall fisherman, cast in bronze, has looked out over Gloucester Harbor from his position on Stacy Boulevard since 1925.

Go Whale Watching

Gloucester's proximity to Stellwagen Bank and Jeffreys Ledge—two nutrient-rich areas on the ocean floor that are like banquet tables for whales—make it one of the best New England ports for a whale watching voyage. Several whale watching companies offer frequent departures from Gloucester during the season when whales are feeding: typically mid-April through October.

Both ​Cape Ann Whale Watch and 7 Seas Whale Watch guarantee whale sightings, which means if you don't spy a whale, you'll be offered free tickets for a future trip.

Play on Good Harbor Beach

While Gloucester has several beautiful beaches to explore, Good Harbor Beach is the prettiest. In addition to views of the Twin Lighthouses on Thacher Island and of smaller Salt Island (which you can walk to at low tide), you can surf the waves or walk the sand year-round. Good Harbor is an ideal spot to swim, boogie board, play beach volleyball, and build sandcastles in the summer.

If you book a stay at Blue Shutters Beachside Inn, you'll be steps from Good Harbor Beach with an incredible ocean view right from the living room couch.

Visit Rocky Neck Art Colony's Studios and Gallery

There's something about the light in Gloucester and this rocky peninsula's natural beauty that has beckoned to artists for nearly two centuries. Don't miss the chance to see artists at work and shop for their one-of-a-kind creations at Rocky Neck Art Colony, the oldest continually working art colony in America. There are 15 galleries on this waterside strip of land where visitors can browse work by painters, photographers, potters, jewelry makers, and textile designers. Float Gallery is a new addition to the scene that features new work by local artists. The exhibitions change each month.

East Gloucester is home to five studios specializing in woodworking, ceramics, watercolor painting, sculpture, and more if you need more art in your life.

Feast on Fresh Seafood at Gloucester House

You'd be missing out if you visited Gloucester and didn't sample some fresh-caught Atlantic seafood. Commercial boats catch haddock, cod, tuna, and New England's favorite crustaceans: lobsters. ​The Gloucester House, a fixture on Seven Seas Wharf since 1958, is a reliable place to satisfy your seafood cravings, from raw oysters to pan-seared tuna to lobster rolls, served either warm with butter or chilled with mayo and celery. Lobster pie, lobster carbonara, even lobster stuffed lobster—the menu is loaded with indulgences, and the service is warm and welcoming.

Be Amazed by the Wonders of Hammond Castle

Gloucester is home, oddly enough, to a medieval-style castle. This fortress on the coast built with Cape Ann granite was completed in 1929 for prolific inventor and avid art collector John Hays Hammond Jr. Several of the castle's windows, stone archways, and wooden facades were a part of Hammond's collection and date as far back as the Classical period.

On a self-guided tour of Hammond Castle, you'll see marvels like the Great Hall's organ with its 8,200 pipes and a 30,000-gallon swimming pool that can be switched from fresh to saltwater with the switch of a lever. The attraction's season ends each year with Holidays at the Castle when Gloucester businesses and organizations deck the halls. Special events include a craft fair, holiday concerts, and a visit from Santa Claus.

Explore Maritime Art and History at Cape Ann Museum

Founded in 1875, this cultural institution documents centuries of maritime art inspired by Cape Ann and the rest of the region. It boasts the most extensive collection of Fitz Henry Lane (a Gloucester native), along with works by John Sloan, Katharine Lane Weems, and Milton Avery. The museum also highlights works from current-day Cape Ann artists.

Beyond fine art, the museum's campus is home to two sculpture gardens, a 19th-century captain's house, and a library.

Dine Overlooking the Water at the Beauport Hotel

Gloucester's swanky Beauport Hotel, which opened in 2016, offers a bit of luxury in this rough and tumble fishing town. Even if you don't stay overnight (the rooftop pool, whirlpool, and bar will sure make you want to in the summer), be sure to make a reservation for dinner. There are phenomenal water views at 1606 Restaurant & Bar and creative cocktails and a menu that features predominantly steaks and seafood, including raw bar selections. There's live music in the cozy bar every Wednesday and Thursday evening.

Walk Through the Home of a Famous Interior Designer

Henry Davis Sleeper was one of the first professional interior designers in the U.S., and his Gloucester summer home offers a unique look into his life and interests. Beauport, the Sleeper-McCann House took decades to complete and evolved throughout Sleeper's life. After he died in 1935, the house was preserved much as he left it. Now a museum and a National Historic Landmark, visitors can tour the mansion and explore each of the highly-decorated rooms. There are more than 40, and no two are alike!

See Gloucester From the Water

One of the best ways to truly experience life in Gloucester is on the water. Whether you want to take a scenic sail aboard a historic schooner, enjoy a narrated cruise through a tidal estuary, or charter a fishing excursion, there's a Gloucester boat for you. Many of Gloucester's boat operators offer private charters if a public tour isn't appealing.

Fans of the National Geographic show "Wicked Tuna" can join a charter fishing trip aboard F/V Hard Merchandise, Captain Dave Marciano's ship. Charters run from April 15 to July 10, and if you catch a giant tuna, you can get a cut of the sale.