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.
The Inn at Good Harbor Beach
Wake to ocean breezes at The Inn at Good Harbor Beach, a beachfront retreat offering refined comfort and direct access to one of Gloucester’s most beloved sandy shores.
Maritime Gloucester
Explore Gloucester’s working waterfront at Maritime Gloucester, an interactive marine science and maritime history center offering exhibits, harbor views, and hands-on experiences for all ages.
Cape Ann Museum
Discover Cape Ann’s rich history and vibrant art scene at Cape Ann Museum, featuring regional art, maritime exhibits, and engaging programs that celebrate the cultural heritage of Gloucester and surrounding communities.
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.
Things to Do
Learn traditional woodcarving at Calvo Woodcarving School with master carver David Calvo, offering hands-on...
Explore Rocky Neck Art Colony, a historic waterfront district filled with galleries, working artists,...
Unwind at Half Moon Beach, a sheltered crescent-shaped cove within Stage Fort Park offering calm waters,...
Set sail aboard Artemis, a 64-foot yacht offering custom 3–4 hour charters along Cape Ann. Enjoy ocean...
Discover rugged coastal beauty at Folly Cove Beach, a dramatic Atlantic cove known for granite cliffs,...
Discover Gloucester’s darker side on the Haunted Harborwalk, a guided evening tour blending local legends,...
Perched above Gloucester Harbor, Beauport, the Sleeper-McCann House offers a colorful, art-filled historic...
Step into history at this elegant Georgian home of Judith Sargent Murray, featuring period furnishings,...
Step into Melody Phaneuf’s charming Centennial Avenue studio to explore luminous Cape Ann-inspired paintings,...
America's only operating twin lighthouses, these iconic 124-foot granite towers have guided mariners...
Five square miles of wild, historic woodland spanning Gloucester and Rockport — Dogtown's glacial boulders,...
Enjoy family-friendly fun at Cape Ann Lanes, featuring 16 candlepin bowling lanes, automatic scoring,...
Experience intimate, thought-provoking performance at Lanes Coven Theater Co., presenting original and...
A Cape Ann yoga community rooted in tradition and open to all. Treetop offers expert-led classes, retreats,...
From sweeping coastal beaches to historic estates and serene woodland trails, The Trustees steward some...
Standing watch over Gloucester's inner harbor since 1821, this iconic 30-foot cast-iron lighthouse tower...
Sail aboard Schooner Lannon and explore Gloucester’s harbor and coastline on a classic schooner, with...
Where the arts come alive under the summer sky — Windhover Performing Arts Center brings world-class...
Where art meets the sea.
Unveiled in 1925, Gloucester's beloved "Man at the Wheel" honors over 5,000 fishermen lost at sea since...
Get outside with North Shore Adventures and Outdoor Center, offering kayaking, paddleboarding, biking,...
Discover vibrant mosaic art and sculpture by Cindy Efinger in Gloucester, featuring colorful, coastal-inspired...
Explore fine art and custom framing at Charles Fine Arts, a longtime Downtown Gloucester gallery featuring...
Follow the Gloucester HarborWalk for a self-guided stroll through maritime history, granite markers,...
A heartfelt tribute honoring Gloucester's WWII veterans, merchant seamen, and the families who sacrificed...
Discover contemporary and plein air paintings at Michalak Fine Art on Rocky Neck, where artist Vanessa...
Experience Off Cabot in downtown Gloucester, an intimate historic venue offering live music, comedy,...
Explore Cape Ann by sea with Agawam Boat & Fishing Charters, offering private fishing and sightseeing...
Head out to sea with Cape Ann Whale Watch for unforgettable trips to Stellwagen Bank aboard the Hurricane...
An active aid to navigation since 1832, Eastern Point Lighthouse marks the entrance to Gloucester Harbor...
Discover the Rockport Art Association & Museum, a historic cultural hub showcasing fine art, sculpture,...
Relax at Wingaersheek Beach, a beloved sandy stretch on the Annisquam River known for gentle waves, wide...
Discover Sawyer Free Library, Gloucester’s historic and modern community hub, offering books, archives,...
Experience live music, film, and performing arts at The Cabot, a beautifully restored historic movie...
A powerful tribute to the women and children who waited ashore, this 12-foot bronze statue honors the...
Explore North Shore Arts Association, a historic harborside gallery showcasing diverse works by regional...
Experience Gloucester’s maritime heritage from the water with Maritime Heritage Charters, offering unforgettable...
Revive Wellness in Gloucester offers holistic therapies, yoga, cryotherapy, saunas, and light and PEMF...
Step back in time at Cogswell’s Grant, a historic salt marsh farm in Essex offering guided tours, gardens,...
Host an unforgettable event on the water with Cape Ann Cruises, offering private charters, customizable...
Discover Cape Ann’s rich history and vibrant art scene at Cape Ann Museum, featuring regional art, maritime...
Visit Stephen LaPierre’s Harbor Loop studio to watch oil painting in action and explore vibrant plein...
Head offshore with Tuna Hunter for an unforgettable Gloucester fishing charter — targeting giant bluefin...
Relax and play at Long Beach, a family-friendly shoreline with soft sand, gentle surf, stunning views...
Walk Gloucester's iconic 2,250-foot granite jetty stretching into the Atlantic, with Gloucester Harbor...
Experience Rockport Music at the stunning Shalin Liu Performance Center, where world-class musicians...
Discover wearable art and vintage style at Juliet Lockwood Studios, a creative studio blending fashion,...
Discover Essex’s maritime heritage at the Essex Historical Society & Shipbuilding Museum, celebrating...
From late-April through mid-October, 7 Seas Whale Watch offers unforgettable daily excursions to Stellwagen...
Founded in 1980, Cape Ann Artisans connects visitors with a self-guided tour of artists’ studios in Gloucester...
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