Directory of Things to Do in Gloucester, MA

Things to Do

Cogswell's Grant

Step back in time at Cogswell’s Grant, a historic salt marsh farm in Essex offering guided tours, gardens,...

Rockport Music

Experience Rockport Music at the stunning Shalin Liu Performance Center, where world-class musicians...

Joe's Fresh Fish Prints

Bring home a piece of the harbor with Joe's Fresh Fish Prints, featuring original Gyotaku fish prints...

The Trustees of Reservations

From sweeping coastal beaches to historic estates and serene woodland trails, The Trustees steward some...

The Cabot

Experience live music, film, and performing arts at The Cabot, a beautifully restored historic movie...

Off Cabot

Experience Off Cabot in downtown Gloucester, an intimate historic venue offering live music, comedy,...

Cape Ann Lanes

Enjoy family-friendly fun at Cape Ann Lanes, featuring 16 candlepin bowling lanes, automatic scoring,...

Windhover Performing Arts Center

Where the arts come alive under the summer sky — Windhover Performing Arts Center brings world-class...

Haunted Harborwalk

Discover Gloucester’s darker side on the Haunted Harborwalk, a guided evening tour blending local legends,...

Essex River Cruises

Essex River Cruises offer narrated sightseeing cruises, private charters, and clambakes, along scenic...

Gloucester Fishermen's Wives Memorial

A powerful tribute to the women and children who waited ashore, this 12-foot bronze statue honors the...

Plum Cove Beach

Enjoy a peaceful retreat at Plum Cove Beach, a sheltered, family-friendly cove with calm waters, scenic...

The Sargent House Museum

Step into history at this elegant Georgian home of Judith Sargent Murray, featuring period furnishings,...

Michalak Fine Art

Discover contemporary and plein air paintings at Michalak Fine Art on Rocky Neck, where artist Vanessa...

Revive Wellness

Revive Wellness in Gloucester offers holistic therapies, yoga, cryotherapy, saunas, and light and PEMF...

Exterior of the Beauport Sleeper McCann House

Beauport, the Sleeper-McCann House

Perched above Gloucester Harbor, Beauport, the Sleeper-McCann House offers a colorful, art-filled historic...

Charles Fine Arts

Explore fine art and custom framing at Charles Fine Arts, a longtime Downtown Gloucester gallery featuring...

Half Moon Beach

Unwind at Half Moon Beach, a sheltered crescent-shaped cove within Stage Fort Park offering calm waters,...

7 Seas Whale Watch

From late-April through mid-October, 7 Seas Whale Watch offers unforgettable daily excursions to Stellwagen...

Cape Ann Cruises

Host an unforgettable event on the water with Cape Ann Cruises, offering private charters, customizable...

Lanes Coven Theater Co.

Experience intimate, thought-provoking performance at Lanes Coven Theater Co., presenting original and...

Cindy Efinger Mosaic and Sculpture

Discover vibrant mosaic art and sculpture by Cindy Efinger in Gloucester, featuring colorful, coastal-inspired...

Gloucester Stage Company

Experience live theater at Gloucester Stage Company, an intimate waterfront venue presenting professional...

Gloucester HarborWalk

Follow the Gloucester HarborWalk for a self-guided stroll through maritime history, granite markers,...

Hammond Castle Museum

Step into medieval-inspired wonder at Hammond Castle Museum, the seaside home of inventor John Hays Hammond...

Eastern Point Lighthouse

An active aid to navigation since 1832, Eastern Point Lighthouse marks the entrance to Gloucester Harbor...

North Shore Arts Association

Explore North Shore Arts Association, a historic harborside gallery showcasing diverse works by regional...

Joan of Arc Statue

A 1921 gift from France, this stunning equestrian bronze by Anna Hyatt Huntington honors Gloucester's...

Beauport Cruiselines

See Gloucester from the water with Beauport Cruiselines, offering scenic sunset and cocktail cruises,...

Amend Bish Gallery

Located in Downtown Gloucester, Amend Bish Gallery features the vibrant paintings of Elizabeth Bish and...

Straitsmouth Island Lighthouse

Perched on a wildlife sanctuary island since 1835, this charming brick lighthouse marks the entrance...

Fisherman's Memorial Statue

Unveiled in 1925, Gloucester's beloved "Man at the Wheel" honors over 5,000 fishermen lost at sea since...

North Shore Adventures

Get outside with North Shore Adventures and Outdoor Center, offering kayaking, paddleboarding, biking,...

Schooner Thomas E. Lannon

Sail aboard Schooner Lannon and explore Gloucester’s harbor and coastline on a classic schooner, with...

Cape Ann Museum

Discover Cape Ann’s rich history and vibrant art scene at Cape Ann Museum, featuring regional art, maritime...

Tuna Hunter Fishing Charters

Head offshore with Tuna Hunter for an unforgettable Gloucester fishing charter — targeting giant bluefin...

Calvo Wood Carving School

Learn traditional woodcarving at Calvo Woodcarving School with master carver David Calvo, offering hands-on...

Juliet Lockwood Studios

Discover wearable art and vintage style at Juliet Lockwood Studios, a creative studio blending fashion,...

Thacher Island Twin Lighthouses

America's only operating twin lighthouses, these iconic 124-foot granite towers have guided mariners...

Stephen LaPierre

Visit Stephen LaPierre’s Harbor Loop studio to watch oil painting in action and explore vibrant plein...

Gloucester City Hall

Admire historic Gloucester City Hall, a landmark overlooking City Hall Plaza and Gloucester Harbor, offering...

Cape Ann Artisans

Founded in 1980, Cape Ann Artisans connects visitors with a self-guided tour of artists’ studios in Gloucester...

Long Beach

Relax and play at Long Beach, a family-friendly shoreline with soft sand, gentle surf, stunning views...

Fitz Henry Lane House

The Cut

Catch live music at The Cut in Gloucester, featuring local and touring bands, energetic performances,...

Niles Beach

Enjoy serene coastal views at Niles Beach, a quiet East Gloucester spot perfect for swimming, wading,...

Folly Cove

Discover rugged coastal beauty at Folly Cove Beach, a dramatic Atlantic cove known for granite cliffs,...

Essex Historical Society & Shipbuilding Museum

Discover Essex’s maritime heritage at the Essex Historical Society & Shipbuilding Museum, celebrating...

World War II Memorial

A heartfelt tribute honoring Gloucester's WWII veterans, merchant seamen, and the families who sacrificed...

Agawam Boat & Fishing Charters

Explore Cape Ann by sea with Agawam Boat & Fishing Charters, offering private fishing and sightseeing...

Cressy's Beach

Relax at Cressy’s Beach, a quiet, rocky harbor-facing beach in Stage Fort Park offering panoramic harbor...

Local Colors Artists' Cooperative

Experience intimate, thought-provoking performance at Lanes Coven Theater Co., presenting original and...

Treetop Yoga

A Cape Ann yoga community rooted in tradition and open to all. Treetop offers expert-led classes, retreats,...

Maritime Gloucester

Explore Gloucester’s working waterfront at Maritime Gloucester, an interactive marine science and maritime...

Rocky Neck Art Colony

Explore Rocky Neck Art Colony, a historic waterfront district filled with galleries, working artists,...

Greenbelt, Essex County’s Land Trust

Explore Gloucester’s natural beauty with Essex County Greenbelt Association, offering free, dog-friendly...

Cape Ann Camp Site

Enjoy a classic outdoor stay at Cape Ann Camp Site, offering wooded campsites and RV hookups near Gloucester’s...

Cape Ann Whale Watch

Head out to sea with Cape Ann Whale Watch for unforgettable trips to Stellwagen Bank aboard the Hurricane...

Ravenswood Park

Explore Ravenswood Park, Gloucester's expansive woodland reserve featuring scenic carriage trails, granite...

Artemis 3 or 4 Hour Sailing Charters

Set sail aboard Artemis, a 64-foot yacht offering custom 3–4 hour charters along Cape Ann. Enjoy ocean...

Beth Williams

Discover contemporary handmade jewelry at Beth Williams Studio, where glass, gold, and silver come together...

Sawyer Free Library

Discover Sawyer Free Library, Gloucester’s historic and modern community hub, offering books, archives,...

Wingaersheek Beach

Relax at Wingaersheek Beach, a beloved sandy stretch on the Annisquam River known for gentle waves, wide...

Gloucester Meetinghouse Foundation

Step inside history at the Gloucester Meetinghouse, where the Gloucester Meetinghouse Foundation presents...

Schooner Adventure

Step aboard Schooner Adventure, a restored 1926 National Historic Landmark, and experience Gloucester’s...

Pavilion Beach

Enjoy waterfront views at Pavilion Beach, a small, charming beach beside downtown Gloucester, perfect...

Dogtown

Five square miles of wild, historic woodland spanning Gloucester and Rockport — Dogtown's glacial boulders,...

Rockport Art Association & Museum

Discover the Rockport Art Association & Museum, a historic cultural hub showcasing fine art, sculpture,...

Maritime Heritage Charters

Experience Gloucester’s maritime heritage from the water with Maritime Heritage Charters, offering unforgettable...

Dog Bar (at Eastern Point Lighthouse)

Walk Gloucester's iconic 2,250-foot granite jetty stretching into the Atlantic, with Gloucester Harbor...

Melody Phaneuf Paintings

Step into Melody Phaneuf’s charming Centennial Avenue studio to explore luminous Cape Ann-inspired paintings,...

Good Harbor Beach

Relax and play at Good Harbor Beach, a wide, family-friendly Atlantic beach with soft sand, gentle surf,...

Cape Ann Harbor Tours

See Gloucester from the water with Cape Ann Harbor Tours, offering narrated lighthouse cruises, harbor...

Annisquam Harbor Lighthouse (Annisquam Light)

One of Gloucester's oldest lighthouses, the 41-foot brick Annisquam Light has marked the entrance to...

Halibut Point State Park

Perched at the northern tip of Cape Ann, this rugged coastal park offers sweeping ocean views, scenic...

Ten Pound Island Lighthouse

Standing watch over Gloucester's inner harbor since 1821, this iconic 30-foot cast-iron lighthouse tower...