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.
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Unforgettable Gloucester: 15 Places Every Visitor Should Explore
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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.
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.
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.
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.
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.
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.
Things to Do
Enjoy waterfront views at Pavilion Beach, a small, charming beach beside downtown Gloucester, perfect...
Experience intimate, thought-provoking performance at Lanes Coven Theater Co., presenting original and...
Explore Gloucester’s natural beauty with Essex County Greenbelt Association, offering free, dog-friendly...
Discover wearable art and vintage style at Juliet Lockwood Studios, a creative studio blending fashion,...
Bring home a piece of the harbor with Joe's Fresh Fish Prints, featuring original Gyotaku fish prints...
Relax and play at Long Beach, a family-friendly shoreline with soft sand, gentle surf, stunning views...
Revive Wellness in Gloucester offers holistic therapies, yoga, cryotherapy, saunas, and light and PEMF...
Perched above Gloucester Harbor, Beauport, the Sleeper-McCann House offers a colorful, art-filled historic...
Experience Rockport Music at the stunning Shalin Liu Performance Center, where world-class musicians...
See Gloucester from the water with Beauport Cruiselines, offering scenic sunset and cocktail cruises,...
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,...
A heartfelt tribute honoring Gloucester's WWII veterans, merchant seamen, and the families who sacrificed...
Host an unforgettable event on the water with Cape Ann Cruises, offering private charters, customizable...
Follow the Gloucester HarborWalk for a self-guided stroll through maritime history, granite markers,...
Perched on a wildlife sanctuary island since 1835, this charming brick lighthouse marks the entrance...
Explore Cape Ann by sea with Agawam Boat & Fishing Charters, offering private fishing and sightseeing...
Step inside history at the Gloucester Meetinghouse, where the Gloucester Meetinghouse Foundation presents...
Discover Sawyer Free Library, Gloucester’s historic and modern community hub, offering books, archives,...
Where the arts come alive under the summer sky — Windhover Performing Arts Center brings world-class...
America's only operating twin lighthouses, these iconic 124-foot granite towers have guided mariners...
Step aboard Schooner Adventure, a restored 1926 National Historic Landmark, and experience Gloucester’s...
Five square miles of wild, historic woodland spanning Gloucester and Rockport — Dogtown's glacial boulders,...
Designed by luminist painter Fitz Henry Lane and built in 1848, this granite Gothic Revival home overlooks...
Founded in 1980, Cape Ann Artisans connects visitors with a self-guided tour of artists’ studios in Gloucester...
Enjoy a peaceful retreat at Plum Cove Beach, a sheltered, family-friendly cove with calm waters, scenic...
A 1921 gift from France, this stunning equestrian bronze by Anna Hyatt Huntington honors Gloucester's...
Relax at Cressy’s Beach, a quiet, rocky harbor-facing beach in Stage Fort Park offering panoramic harbor...
Relax and play at Good Harbor Beach, a wide, family-friendly Atlantic beach with soft sand, gentle surf,...
Unwind at Half Moon Beach, a sheltered crescent-shaped cove within Stage Fort Park offering calm waters,...
Enjoy family-friendly fun at Cape Ann Lanes, featuring 16 candlepin bowling lanes, automatic scoring,...
Explore fine art and custom framing at Charles Fine Arts, a longtime Downtown Gloucester gallery featuring...
Essex River Cruises offer narrated sightseeing cruises, private charters, and clambakes, along scenic...
Step into Melody Phaneuf’s charming Centennial Avenue studio to explore luminous Cape Ann-inspired paintings,...
Head offshore with Tuna Hunter for an unforgettable Gloucester fishing charter — targeting giant bluefin...
From late-April through mid-October, 7 Seas Whale Watch offers unforgettable daily excursions to Stellwagen...
Get outside with North Shore Adventures and Outdoor Center, offering kayaking, paddleboarding, biking,...
Catch live music at The Cut in Gloucester, featuring local and touring bands, energetic performances,...
Experience live music, film, and performing arts at The Cabot, a beautifully restored historic movie...
Visit Stephen LaPierre’s Harbor Loop studio to watch oil painting in action and explore vibrant plein...
Experience live theater at Gloucester Stage Company, an intimate waterfront venue presenting professional...
Located in Downtown Gloucester, Amend Bish Gallery features the vibrant paintings of Elizabeth Bish and...
Discover Essex’s maritime heritage at the Essex Historical Society & Shipbuilding Museum, celebrating...
One of Gloucester's oldest lighthouses, the 41-foot brick Annisquam Light has marked the entrance to...
Admire historic Gloucester City Hall, a landmark overlooking City Hall Plaza and Gloucester Harbor, offering...
Step into medieval-inspired wonder at Hammond Castle Museum, the seaside home of inventor John Hays Hammond...
Head out to sea with Cape Ann Whale Watch for unforgettable trips to Stellwagen Bank aboard the Hurricane...
A Cape Ann yoga community rooted in tradition and open to all. Treetop offers expert-led classes, retreats,...
Sail aboard Schooner Lannon and explore Gloucester’s harbor and coastline on a classic schooner, with...
Unveiled in 1925, Gloucester's beloved "Man at the Wheel" honors over 5,000 fishermen lost at sea since...
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