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
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.
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.
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.
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.
Things to Do
Enjoy waterfront views at Pavilion Beach, a small, charming beach beside downtown Gloucester, perfect...
Perched above Gloucester Harbor, Beauport, the Sleeper-McCann House offers a colorful, art-filled historic...
Explore Ravenswood Park, Gloucester's expansive woodland reserve featuring scenic carriage trails, granite...
Explore Cape Ann by sea with Agawam Boat & Fishing Charters, offering private fishing and sightseeing...
Step into medieval-inspired wonder at Hammond Castle Museum, the seaside home of inventor John Hays Hammond...
Get outside with North Shore Adventures and Outdoor Center, offering kayaking, paddleboarding, biking,...
From sweeping coastal beaches to historic estates and serene woodland trails, The Trustees steward some...
Set sail aboard Artemis, a 64-foot yacht offering custom 3–4 hour charters along Cape Ann. Enjoy ocean...
Discover contemporary and plein air paintings at Michalak Fine Art on Rocky Neck, where artist Vanessa...
Sail aboard Schooner Lannon and explore Gloucester’s harbor and coastline on a classic schooner, with...
Five square miles of wild, historic woodland spanning Gloucester and Rockport — Dogtown's glacial boulders,...
Unveiled in 1925, Gloucester's beloved "Man at the Wheel" honors over 5,000 fishermen lost at sea since...
A Cape Ann yoga community rooted in tradition and open to all. Treetop offers expert-led classes, retreats,...
Discover the Rockport Art Association & Museum, a historic cultural hub showcasing fine art, sculpture,...
See Gloucester from the water with Beauport Cruiselines, offering scenic sunset and cocktail cruises,...
Discover vibrant mosaic art and sculpture by Cindy Efinger in Gloucester, featuring colorful, coastal-inspired...
Revive Wellness in Gloucester offers holistic therapies, yoga, cryotherapy, saunas, and light and PEMF...
Experience Rockport Music at the stunning Shalin Liu Performance Center, where world-class musicians...
Step into history at this elegant Georgian home of Judith Sargent Murray, featuring period furnishings,...
Step back in time at Cogswell’s Grant, a historic salt marsh farm in Essex offering guided tours, gardens,...
Bring home a piece of the harbor with Joe's Fresh Fish Prints, featuring original Gyotaku fish prints...
Step aboard Schooner Adventure, a restored 1926 National Historic Landmark, and experience Gloucester’s...
Located in Downtown Gloucester, Amend Bish Gallery features the vibrant paintings of Elizabeth Bish and...
A 1921 gift from France, this stunning equestrian bronze by Anna Hyatt Huntington honors Gloucester's...
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,...
From late-April through mid-October, 7 Seas Whale Watch offers unforgettable daily excursions to Stellwagen...
Walk Gloucester's iconic 2,250-foot granite jetty stretching into the Atlantic, with Gloucester Harbor...
Founded in 1980, Cape Ann Artisans connects visitors with a self-guided tour of artists’ studios in Gloucester...
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,...
Explore Gloucester’s working waterfront at Maritime Gloucester, an interactive marine science and maritime...
Experience intimate, thought-provoking performance at Lanes Coven Theater Co., presenting original and...
Experience live music, film, and performing arts at The Cabot, a beautifully restored historic movie...
Designed by luminist painter Fitz Henry Lane and built in 1848, this granite Gothic Revival home overlooks...
Discover wearable art and vintage style at Juliet Lockwood Studios, a creative studio blending fashion,...
Perched on a wildlife sanctuary island since 1835, this charming brick lighthouse marks the entrance...
Relax at Cressy’s Beach, a quiet, rocky harbor-facing beach in Stage Fort Park offering panoramic harbor...
Relax and play at Long Beach, a family-friendly shoreline with soft sand, gentle surf, stunning views...
Explore Rocky Neck Art Colony, a historic waterfront district filled with galleries, working artists,...
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...
Experience Off Cabot in downtown Gloucester, an intimate historic venue offering live music, comedy,...
Enjoy a peaceful retreat at Plum Cove Beach, a sheltered, family-friendly cove with calm waters, scenic...
Relax at Wingaersheek Beach, a beloved sandy stretch on the Annisquam River known for gentle waves, wide...
Explore Gloucester’s natural beauty with Essex County Greenbelt Association, offering free, dog-friendly...
Admire historic Gloucester City Hall, a landmark overlooking City Hall Plaza and Gloucester Harbor, offering...
Catch live music at The Cut in Gloucester, featuring local and touring bands, energetic performances,...
Follow the Gloucester HarborWalk for a self-guided stroll through maritime history, granite markers,...
Experience Gloucester’s maritime heritage from the water with Maritime Heritage Charters, offering unforgettable...
1
2