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
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.
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.
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.
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.
Hammond Castle Museum
Step into medieval-inspired wonder at Hammond Castle Museum, the seaside home of inventor John Hays Hammond Jr., featuring dramatic architecture, ocean views, and fascinating collections overlooking Gloucester’s rugged coast.
Things to Do
Discover contemporary handmade jewelry at Beth Williams Studio, where glass, gold, and silver come together...
Where the arts come alive under the summer sky — Windhover Performing Arts Center brings world-class...
Explore Ravenswood Park, Gloucester's expansive woodland reserve featuring scenic carriage trails, granite...
Relax and play at Long Beach, a family-friendly shoreline with soft sand, gentle surf, stunning views...
Explore Cape Ann by sea with Agawam Boat & Fishing Charters, offering private fishing and sightseeing...
Step aboard Schooner Adventure, a restored 1926 National Historic Landmark, and experience Gloucester’s...
Perched above Gloucester Harbor, Beauport, the Sleeper-McCann House offers a colorful, art-filled historic...
Located in Downtown Gloucester, Amend Bish Gallery features the vibrant paintings of Elizabeth Bish and...
Five square miles of wild, historic woodland spanning Gloucester and Rockport — Dogtown's glacial boulders,...
Discover the Rockport Art Association & Museum, a historic cultural hub showcasing fine art, sculpture,...
Discover Cape Ann’s rich history and vibrant art scene at Cape Ann Museum, featuring regional art, maritime...
Explore Gloucester’s natural beauty with Essex County Greenbelt Association, offering free, dog-friendly...
Head offshore with Tuna Hunter for an unforgettable Gloucester fishing charter — targeting giant bluefin...
Discover Gloucester’s darker side on the Haunted Harborwalk, a guided evening tour blending local legends,...
Explore North Shore Arts Association, a historic harborside gallery showcasing diverse works by regional...
Relax and play at Good Harbor Beach, a wide, family-friendly Atlantic beach with soft sand, gentle surf,...
Explore Gloucester’s working waterfront at Maritime Gloucester, an interactive marine science and maritime...
Admire historic Gloucester City Hall, a landmark overlooking City Hall Plaza and Gloucester Harbor, offering...
Unveiled in 1925, Gloucester's beloved "Man at the Wheel" honors over 5,000 fishermen lost at sea since...
Explore Rocky Neck Art Colony, a historic waterfront district filled with galleries, working artists,...
Experience intimate, thought-provoking performance at Lanes Coven Theater Co., presenting original and...
Discover Sawyer Free Library, Gloucester’s historic and modern community hub, offering books, archives,...
From sweeping coastal beaches to historic estates and serene woodland trails, The Trustees steward some...
Follow the Gloucester HarborWalk for a self-guided stroll through maritime history, granite markers,...
Discover Essex’s maritime heritage at the Essex Historical Society & Shipbuilding Museum, celebrating...
Sail aboard Schooner Lannon and explore Gloucester’s harbor and coastline on a classic schooner, with...
Experience live theater at Gloucester Stage Company, an intimate waterfront venue presenting professional...
See Gloucester from the water with Cape Ann Harbor Tours, offering narrated lighthouse cruises, harbor...
From late-April through mid-October, 7 Seas Whale Watch offers unforgettable daily excursions to Stellwagen...
Set sail aboard Artemis, a 64-foot yacht offering custom 3–4 hour charters along Cape Ann. Enjoy ocean...
Relax at Wingaersheek Beach, a beloved sandy stretch on the Annisquam River known for gentle waves, wide...
Host an unforgettable event on the water with Cape Ann Cruises, offering private charters, customizable...
Unwind at Half Moon Beach, a sheltered crescent-shaped cove within Stage Fort Park offering calm waters,...
Relax at Cressy’s Beach, a quiet, rocky harbor-facing beach in Stage Fort Park offering panoramic harbor...
Experience Off Cabot in downtown Gloucester, an intimate historic venue offering live music, comedy,...
Discover contemporary and plein air paintings at Michalak Fine Art on Rocky Neck, where artist Vanessa...
See Gloucester from the water with Beauport Cruiselines, offering scenic sunset and cocktail cruises,...
Enjoy a peaceful retreat at Plum Cove Beach, a sheltered, family-friendly cove with calm waters, scenic...
Discover vibrant mosaic art and sculpture by Cindy Efinger in Gloucester, featuring colorful, coastal-inspired...
Founded in 1980, Cape Ann Artisans connects visitors with a self-guided tour of artists’ studios in Gloucester...
Experience Rockport Music at the stunning Shalin Liu Performance Center, where world-class musicians...
America's only operating twin lighthouses, these iconic 124-foot granite towers have guided mariners...
Get outside with North Shore Adventures and Outdoor Center, offering kayaking, paddleboarding, biking,...
Enjoy waterfront views at Pavilion Beach, a small, charming beach beside downtown Gloucester, perfect...
Walk Gloucester's iconic 2,250-foot granite jetty stretching into the Atlantic, with Gloucester Harbor...
Discover wearable art and vintage style at Juliet Lockwood Studios, a creative studio blending fashion,...
Visit Stephen LaPierre’s Harbor Loop studio to watch oil painting in action and explore vibrant plein...
Experience Gloucester’s maritime heritage from the water with Maritime Heritage Charters, offering unforgettable...
Explore fine art and custom framing at Charles Fine Arts, a longtime Downtown Gloucester gallery featuring...
Step into Melody Phaneuf’s charming Centennial Avenue studio to explore luminous Cape Ann-inspired paintings,...
1
2