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
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.
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.
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.
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.
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
Catch live music at The Cut in Gloucester, featuring local and touring bands, energetic performances,...
Relax and play at Good Harbor Beach, a wide, family-friendly Atlantic beach with soft sand, gentle surf,...
Host an unforgettable event on the water with Cape Ann Cruises, offering private charters, customizable...
Discover Sawyer Free Library, Gloucester’s historic and modern community hub, offering books, archives,...
Perched on a wildlife sanctuary island since 1835, this charming brick lighthouse marks the entrance...
A powerful tribute to the women and children who waited ashore, this 12-foot bronze statue honors the...
Enjoy serene coastal views at Niles Beach, a quiet East Gloucester spot perfect for swimming, wading,...
Explore Rocky Neck Art Colony, a historic waterfront district filled with galleries, working artists,...
Discover Cape Ann’s rich history and vibrant art scene at Cape Ann Museum, featuring regional art, maritime...
From sweeping coastal beaches to historic estates and serene woodland trails, The Trustees steward some...
Essex River Cruises offer narrated sightseeing cruises, private charters, and clambakes, along scenic...
Where art meets the sea.
Relax at Cressy’s Beach, a quiet, rocky harbor-facing beach in Stage Fort Park offering panoramic harbor...
Visit Local Colors Artists' Cooperative for a wide selection of original art from Gloucester and Cape...
Visit Stephen LaPierre’s Harbor Loop studio to watch oil painting in action and explore vibrant plein...
Founded in 1980, Cape Ann Artisans connects visitors with a self-guided tour of artists’ studios in Gloucester...
Get outside with North Shore Adventures and Outdoor Center, offering kayaking, paddleboarding, biking,...
Explore Gloucester’s working waterfront at Maritime Gloucester, an interactive marine science and maritime...
Discover the Rockport Art Association & Museum, a historic cultural hub showcasing fine art, sculpture,...
Follow the Gloucester HarborWalk for a self-guided stroll through maritime history, granite markers,...
Head out to sea with Cape Ann Whale Watch for unforgettable trips to Stellwagen Bank aboard the Hurricane...
Sail aboard Schooner Lannon and explore Gloucester’s harbor and coastline on a classic schooner, with...
See Gloucester from the water with Beauport Cruiselines, offering scenic sunset and cocktail cruises,...
Standing watch over Gloucester's inner harbor since 1821, this iconic 30-foot cast-iron lighthouse tower...
An active aid to navigation since 1832, Eastern Point Lighthouse marks the entrance to Gloucester Harbor...
Discover wearable art and vintage style at Juliet Lockwood Studios, a creative studio blending fashion,...
Where the arts come alive under the summer sky — Windhover Performing Arts Center brings world-class...
Located in Downtown Gloucester, Amend Bish Gallery features the vibrant paintings of Elizabeth Bish and...
A Cape Ann yoga community rooted in tradition and open to all. Treetop offers expert-led classes, retreats,...
Perched above Gloucester Harbor, Beauport, the Sleeper-McCann House offers a colorful, art-filled historic...
Learn traditional woodcarving at Calvo Woodcarving School with master carver David Calvo, offering hands-on...
Explore Cape Ann by sea with Agawam Boat & Fishing Charters, offering private fishing and sightseeing...
Experience Off Cabot in downtown Gloucester, an intimate historic venue offering live music, comedy,...
Discover rugged coastal beauty at Folly Cove Beach, a dramatic Atlantic cove known for granite cliffs,...
Unwind at Half Moon Beach, a sheltered crescent-shaped cove within Stage Fort Park offering calm waters,...
Relax and play at Long Beach, a family-friendly shoreline with soft sand, gentle surf, stunning views...
Discover Gloucester’s darker side on the Haunted Harborwalk, a guided evening tour blending local legends,...
One of Gloucester's oldest lighthouses, the 41-foot brick Annisquam Light has marked the entrance to...
Head offshore with Tuna Hunter for an unforgettable Gloucester fishing charter — targeting giant bluefin...
Revive Wellness in Gloucester offers holistic therapies, yoga, cryotherapy, saunas, and light and PEMF...
Unveiled in 1925, Gloucester's beloved "Man at the Wheel" honors over 5,000 fishermen lost at sea since...
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...
America's only operating twin lighthouses, these iconic 124-foot granite towers have guided mariners...
Explore Gloucester’s natural beauty with Essex County Greenbelt Association, offering free, dog-friendly...
Experience intimate, thought-provoking performance at Lanes Coven Theater Co., presenting original and...
Explore North Shore Arts Association, a historic harborside gallery showcasing diverse works by regional...
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...
Step inside history at the Gloucester Meetinghouse, where the Gloucester Meetinghouse Foundation presents...
1
2