Things to Do
Gloucester offers endless things to do, making it an ideal destination for every type of traveler. Relax on Gloucester’s beautiful beaches, explore scenic parks and coastal trails, or get out on the water with whale watching tours, schooner sails, kayaking, and harbor cruises. Discover a vibrant mix of arts, culture, shopping, and dining, all rooted in the city’s historic working waterfront. Whether you’re looking for adventure or a laid-back seaside escape, Gloucester, Massachusetts offers unforgettable coastal experiences year-round.
Featured Favorites
Unforgettable Gloucester: 15 Places Every Visitor Should Explore
Discover Things to Do
Addison Choate
Rockport’s first boutique hotel blends 1851 charm with modern comforts, walkable to shops, beaches, and Shalin Liu Performance Center. Enjoy luxe rooms, thoughtful amenities, and fresh-baked breakfast each morning.
Minglewood Harborside
Dine at Minglewood Harborside for waterfront views, fresh local seafood, creative sushi, and tavern favorites, with live music, trivia nights, and versatile indoor and outdoor spaces in Gloucester.
Mark Adrian Shoes
A longtime Gloucester staple, Mark Adrian Shoes offers quality footwear, trusted brands, and personalized service to keep visitors and locals comfortable for work, adventure, and everyday style.
7 Seas Whale Watch
From late-April through mid-October, 7 Seas Whale Watch offers unforgettable daily excursions to Stellwagen Bank National Marine Sanctuary, one of the top whale-watching destinations on the East Coast.
Captain’s Bounty on the Beach
Stay oceanfront at Captain’s Bounty on the Beach in Rockport, offering classic New England charm, sweeping Front Beach views, and walkable access to Bearskin Neck shops, galleries, and dining.
Cape Ann Whale Watch
Head out to sea with Cape Ann Whale Watch for unforgettable trips to Stellwagen Bank aboard the Hurricane II, spotting whales in their natural habitat just off Gloucester.
Things to Do
Designed by luminist painter Fitz Henry Lane and built in 1848, this granite Gothic Revival home overlooks...
Explore Gloucester’s working waterfront at Maritime Gloucester, an interactive marine science and maritime...
Explore Cape Ann by sea with Agawam Boat & Fishing Charters, offering private fishing and sightseeing...
Essex River Cruises offer narrated sightseeing cruises, private charters, and clambakes, along scenic...
Relax and play at Good Harbor Beach, a wide, family-friendly Atlantic beach with soft sand, gentle surf,...
Learn traditional woodcarving at Calvo Woodcarving School with master carver David Calvo, offering hands-on...
A 1921 gift from France, this stunning equestrian bronze by Anna Hyatt Huntington honors Gloucester's...
An active aid to navigation since 1832, Eastern Point Lighthouse marks the entrance to Gloucester Harbor...
Perched above Gloucester Harbor, Beauport, the Sleeper-McCann House offers a colorful, art-filled historic...
Discover vibrant mosaic art and sculpture by Cindy Efinger in Gloucester, featuring colorful, coastal-inspired...
See Gloucester from the water with Beauport Cruiselines, offering scenic sunset and cocktail cruises,...
Catch live music at The Cut in Gloucester, featuring local and touring bands, energetic performances,...
Step into history at this elegant Georgian home of Judith Sargent Murray, featuring period furnishings,...
Host an unforgettable event on the water with Cape Ann Cruises, offering private charters, customizable...
Discover contemporary handmade jewelry at Beth Williams Studio, where glass, gold, and silver come together...
Explore North Shore Arts Association, a historic harborside gallery showcasing diverse works by regional...
Head offshore with Tuna Hunter for an unforgettable Gloucester fishing charter — targeting giant bluefin...
See Gloucester from the water with Cape Ann Harbor Tours, offering narrated lighthouse cruises, harbor...
Walk Gloucester's iconic 2,250-foot granite jetty stretching into the Atlantic, with Gloucester Harbor...
Revive Wellness in Gloucester offers holistic therapies, yoga, cryotherapy, saunas, and light and PEMF...
Visit Local Colors Artists' Cooperative for a wide selection of original art from Gloucester and Cape...
Step into Melody Phaneuf’s charming Centennial Avenue studio to explore luminous Cape Ann-inspired paintings,...
Discover the Rockport Art Association & Museum, a historic cultural hub showcasing fine art, sculpture,...
Five square miles of wild, historic woodland spanning Gloucester and Rockport — Dogtown's glacial boulders,...
Sail aboard Schooner Lannon and explore Gloucester’s harbor and coastline on a classic schooner, with...
Visit Stephen LaPierre’s Harbor Loop studio to watch oil painting in action and explore vibrant plein...
Experience intimate, thought-provoking performance at Lanes Coven Theater Co., presenting original and...
Enjoy family-friendly fun at Cape Ann Lanes, featuring 16 candlepin bowling lanes, automatic scoring,...
From late-April through mid-October, 7 Seas Whale Watch offers unforgettable daily excursions to Stellwagen...
Step aboard Schooner Adventure, a restored 1926 National Historic Landmark, and experience Gloucester’s...
Experience live music, film, and performing arts at The Cabot, a beautifully restored historic movie...
Unveiled in 1925, Gloucester's beloved "Man at the Wheel" honors over 5,000 fishermen lost at sea since...
Discover contemporary and plein air paintings at Michalak Fine Art on Rocky Neck, where artist Vanessa...
Explore fine art and custom framing at Charles Fine Arts, a longtime Downtown Gloucester gallery featuring...
Relax at Wingaersheek Beach, a beloved sandy stretch on the Annisquam River known for gentle waves, wide...
One of Gloucester's oldest lighthouses, the 41-foot brick Annisquam Light has marked the entrance to...
Relax at Cressy’s Beach, a quiet, rocky harbor-facing beach in Stage Fort Park offering panoramic harbor...
Explore Gloucester’s natural beauty with Essex County Greenbelt Association, offering free, dog-friendly...
Bring home a piece of the harbor with Joe's Fresh Fish Prints, featuring original Gyotaku fish prints...
Perched on a wildlife sanctuary island since 1835, this charming brick lighthouse marks the entrance...
Discover Gloucester’s darker side on the Haunted Harborwalk, a guided evening tour blending local legends,...
Located in Downtown Gloucester, Amend Bish Gallery features the vibrant paintings of Elizabeth Bish and...
Founded in 1980, Cape Ann Artisans connects visitors with a self-guided tour of artists’ studios in Gloucester...
Perched at the northern tip of Cape Ann, this rugged coastal park offers sweeping ocean views, scenic...
Step back in time at Cogswell’s Grant, a historic salt marsh farm in Essex offering guided tours, gardens,...
Experience Off Cabot in downtown Gloucester, an intimate historic venue offering live music, comedy,...
Unwind at Half Moon Beach, a sheltered crescent-shaped cove within Stage Fort Park offering calm waters,...
Experience Rockport Music at the stunning Shalin Liu Performance Center, where world-class musicians...
Enjoy serene coastal views at Niles Beach, a quiet East Gloucester spot perfect for swimming, wading,...
A Cape Ann yoga community rooted in tradition and open to all. Treetop offers expert-led classes, retreats,...
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