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.
Schooner Thomas E. Lannon
Sail aboard Schooner Lannon and explore Gloucester’s harbor and coastline on a classic schooner, with daily tours, sunset sails, and hands-on opportunities to help raise sails or simply relax.
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.
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.
The Hotel at Cape Ann Marina
Stay waterfront at The Hotel at Cape Ann Marina, offering balcony views of the Annisquam River, indoor pool, and direct access to Mile Marker One Restaurant & Bar year-round.
Mile Marker One
Dine waterfront at Mile Marker One at Cape Ann Marina, where fresh seafood, creative dishes, and vibrant cocktails are served year-round with marina views, live music, and unique seasonal experiences.
Things to Do
Experience live theater at Gloucester Stage Company, an intimate waterfront venue presenting professional...
Unveiled in 1925, Gloucester's beloved "Man at the Wheel" honors over 5,000 fishermen lost at sea since...
From late-April through mid-October, 7 Seas Whale Watch offers unforgettable daily excursions to Stellwagen...
Step into medieval-inspired wonder at Hammond Castle Museum, the seaside home of inventor John Hays Hammond...
Discover contemporary handmade jewelry at Beth Williams Studio, where glass, gold, and silver come together...
Discover Sawyer Free Library, Gloucester’s historic and modern community hub, offering books, archives,...
One of Gloucester's oldest lighthouses, the 41-foot brick Annisquam Light has marked the entrance to...
Step inside history at the Gloucester Meetinghouse, where the Gloucester Meetinghouse Foundation presents...
Located in Downtown Gloucester, Amend Bish Gallery features the vibrant paintings of Elizabeth Bish and...
A powerful tribute to the women and children who waited ashore, this 12-foot bronze statue honors the...
Learn traditional woodcarving at Calvo Woodcarving School with master carver David Calvo, offering hands-on...
Experience Rockport Music at the stunning Shalin Liu Performance Center, where world-class musicians...
See Gloucester from the water with Cape Ann Harbor Tours, offering narrated lighthouse cruises, harbor...
Follow the Gloucester HarborWalk for a self-guided stroll through maritime history, granite markers,...
Explore North Shore Arts Association, a historic harborside gallery showcasing diverse works by regional...
Perched above Gloucester Harbor, Beauport, the Sleeper-McCann House offers a colorful, art-filled historic...
Discover wearable art and vintage style at Juliet Lockwood Studios, a creative studio blending fashion,...
Head offshore with Tuna Hunter for an unforgettable Gloucester fishing charter — targeting giant bluefin...
From sweeping coastal beaches to historic estates and serene woodland trails, The Trustees steward some...
Explore Ravenswood Park, Gloucester's expansive woodland reserve featuring scenic carriage trails, granite...
Catch live music at The Cut in Gloucester, featuring local and touring bands, energetic performances,...
Step into Melody Phaneuf’s charming Centennial Avenue studio to explore luminous Cape Ann-inspired paintings,...
Head out to sea with Cape Ann Whale Watch for unforgettable trips to Stellwagen Bank aboard the Hurricane...
Where the arts come alive under the summer sky — Windhover Performing Arts Center brings world-class...
Unwind at Half Moon Beach, a sheltered crescent-shaped cove within Stage Fort Park offering calm waters,...
Get outside with North Shore Adventures and Outdoor Center, offering kayaking, paddleboarding, biking,...
A heartfelt tribute honoring Gloucester's WWII veterans, merchant seamen, and the families who sacrificed...
Where art meets the sea.
America's only operating twin lighthouses, these iconic 124-foot granite towers have guided mariners...
Experience Gloucester’s maritime heritage from the water with Maritime Heritage Charters, offering unforgettable...
Designed by luminist painter Fitz Henry Lane and built in 1848, this granite Gothic Revival home overlooks...
Revive Wellness in Gloucester offers holistic therapies, yoga, cryotherapy, saunas, and light and PEMF...
Perched at the northern tip of Cape Ann, this rugged coastal park offers sweeping ocean views, scenic...
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...
Step into history at this elegant Georgian home of Judith Sargent Murray, featuring period furnishings,...
Discover Essex’s maritime heritage at the Essex Historical Society & Shipbuilding Museum, celebrating...
Admire historic Gloucester City Hall, a landmark overlooking City Hall Plaza and Gloucester Harbor, offering...
Discover Cape Ann’s rich history and vibrant art scene at Cape Ann Museum, featuring regional art, maritime...
Five square miles of wild, historic woodland spanning Gloucester and Rockport — Dogtown's glacial boulders,...
A 1921 gift from France, this stunning equestrian bronze by Anna Hyatt Huntington honors Gloucester's...
Discover vibrant mosaic art and sculpture by Cindy Efinger in Gloucester, featuring colorful, coastal-inspired...
Explore Gloucester’s working waterfront at Maritime Gloucester, an interactive marine science and maritime...
Set sail aboard Artemis, a 64-foot yacht offering custom 3–4 hour charters along Cape Ann. Enjoy ocean...
Essex River Cruises offer narrated sightseeing cruises, private charters, and clambakes, along scenic...
Experience intimate, thought-provoking performance at Lanes Coven Theater Co., presenting original and...
Enjoy waterfront views at Pavilion Beach, a small, charming beach beside downtown Gloucester, perfect...
Explore fine art and custom framing at Charles Fine Arts, a longtime Downtown Gloucester gallery featuring...
Visit Local Colors Artists' Cooperative for a wide selection of original art from Gloucester and Cape...
Bring home a piece of the harbor with Joe's Fresh Fish Prints, featuring original Gyotaku fish prints...
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