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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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.
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.
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.
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.
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.
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.
Things to Do
Discover Gloucester’s darker side on the Haunted Harborwalk, a guided evening tour blending local legends,...
Enjoy family-friendly fun at Cape Ann Lanes, featuring 16 candlepin bowling lanes, automatic scoring,...
Discover Essex’s maritime heritage at the Essex Historical Society & Shipbuilding Museum, celebrating...
Enjoy a peaceful retreat at Plum Cove Beach, a sheltered, family-friendly cove with calm waters, scenic...
Host an unforgettable event on the water with Cape Ann Cruises, offering private charters, customizable...
Perched at the northern tip of Cape Ann, this rugged coastal park offers sweeping ocean views, scenic...
Five square miles of wild, historic woodland spanning Gloucester and Rockport — Dogtown's glacial boulders,...
Discover contemporary handmade jewelry at Beth Williams Studio, where glass, gold, and silver come together...
From sweeping coastal beaches to historic estates and serene woodland trails, The Trustees steward some...
Explore fine art and custom framing at Charles Fine Arts, a longtime Downtown Gloucester gallery featuring...
Relax and play at Long Beach, a family-friendly shoreline with soft sand, gentle surf, stunning views...
Experience intimate, thought-provoking performance at Lanes Coven Theater Co., presenting original and...
Relax at Wingaersheek Beach, a beloved sandy stretch on the Annisquam River known for gentle waves, wide...
Unveiled in 1925, Gloucester's beloved "Man at the Wheel" honors over 5,000 fishermen lost at sea since...
Discover Cape Ann’s rich history and vibrant art scene at Cape Ann Museum, featuring regional art, maritime...
Explore Ravenswood Park, Gloucester's expansive woodland reserve featuring scenic carriage trails, granite...
A powerful tribute to the women and children who waited ashore, this 12-foot bronze statue honors the...
Revive Wellness in Gloucester offers holistic therapies, yoga, cryotherapy, saunas, and light and PEMF...
Visit Stephen LaPierre’s Harbor Loop studio to watch oil painting in action and explore vibrant plein...
Explore Rocky Neck Art Colony, a historic waterfront district filled with galleries, working artists,...
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,...
Explore Gloucester’s natural beauty with Essex County Greenbelt Association, offering free, dog-friendly...
Perched on a wildlife sanctuary island since 1835, this charming brick lighthouse marks the entrance...
Discover rugged coastal beauty at Folly Cove Beach, a dramatic Atlantic cove known for granite cliffs,...
Enjoy serene coastal views at Niles Beach, a quiet East Gloucester spot perfect for swimming, wading,...
Standing watch over Gloucester's inner harbor since 1821, this iconic 30-foot cast-iron lighthouse tower...
America's only operating twin lighthouses, these iconic 124-foot granite towers have guided mariners...
Catch live music at The Cut in Gloucester, featuring local and touring bands, energetic performances,...
Walk Gloucester's iconic 2,250-foot granite jetty stretching into the Atlantic, with Gloucester Harbor...
Step inside history at the Gloucester Meetinghouse, where the Gloucester Meetinghouse Foundation presents...
Essex River Cruises offer narrated sightseeing cruises, private charters, and clambakes, along scenic...
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...
Relax and play at Good Harbor Beach, a wide, family-friendly Atlantic beach with soft sand, gentle surf,...
Enjoy waterfront views at Pavilion Beach, a small, charming beach beside downtown Gloucester, perfect...
Step back in time at Cogswell’s Grant, a historic salt marsh farm in Essex offering guided tours, gardens,...
Founded in 1980, Cape Ann Artisans connects visitors with a self-guided tour of artists’ studios in Gloucester...
A Cape Ann yoga community rooted in tradition and open to all. Treetop offers expert-led classes, retreats,...
Step into Melody Phaneuf’s charming Centennial Avenue studio to explore luminous Cape Ann-inspired paintings,...
Learn traditional woodcarving at Calvo Woodcarving School with master carver David Calvo, offering hands-on...
Experience Off Cabot in downtown Gloucester, an intimate historic venue offering live music, comedy,...
Explore North Shore Arts Association, a historic harborside gallery showcasing diverse works by regional...
See Gloucester from the water with Cape Ann Harbor Tours, offering narrated lighthouse cruises, harbor...
Visit Local Colors Artists' Cooperative for a wide selection of original art from Gloucester and Cape...
Discover wearable art and vintage style at Juliet Lockwood Studios, a creative studio blending fashion,...
Step aboard Schooner Adventure, a restored 1926 National Historic Landmark, and experience Gloucester’s...
Follow the Gloucester HarborWalk for a self-guided stroll through maritime history, granite markers,...
Bring home a piece of the harbor with Joe's Fresh Fish Prints, featuring original Gyotaku fish prints...
Admire historic Gloucester City Hall, a landmark overlooking City Hall Plaza and Gloucester Harbor, offering...
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