Directory
The Vista
Wake up to breathtaking ocean views at The Vista, a comfortable Gloucester retreat just steps from Good Harbor Beach with a heated pool, continental breakfast, and warm, welcoming service.
Seaport Grille
Dine at Seaport Grille, a local favorite offering fresh seafood, prime meats, and waterfront views from its open-air deck overlooking Gloucester’s working harbor and Cruiseport.
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.
Wingaersheek Beach
Relax at Wingaersheek Beach, a beloved sandy stretch on the Annisquam River known for gentle waves, wide tidal flats, and stunning sunset views over Ipswich Bay.
Local Colors Artists’ Cooperative
Visit Local Colors Artists' Cooperative for a wide selection of original art from Gloucester and Cape Ann Artists.
Amend Bish Gallery
Located in Downtown Gloucester, Amend Bish Gallery features the vibrant paintings of Elizabeth Bish and Tom Amend, capturing Cape Ann landscapes, interiors, and scenes from France with color, light, and thoughtful detail.
Oak to Ember
Oak to Ember in Gloucester features live fire cooking with a coastal American menu, using local ingredients, seafood, and prime meats, plus waterfront dining.
Maritime Heritage Charters
Experience Gloucester’s maritime heritage from the water with Maritime Heritage Charters, offering unforgettable sailing adventures aboard two traditional schooners along the scenic coastline of Cape Ann.
Gloucester Apparel
Shop locally inspired apparel at Gloucester Apparel, offering comfortable, coastal-style clothing and accessories that celebrate Gloucester’s working waterfront and New England pride.
North of Boston Convention & Visitors Bureau
Visit area cities and towns, offering coastal scenic beauty, activities on and off the water, unique shopping and plenty of fresh seafood.
The Gloucester House
Overlooking the working harbor, The Gloucester House serves classic New England seafood in a relaxed waterfront setting steps from downtown, celebrating generations of local fishing tradition year-round.
Agawam Boat & Fishing Charters
Explore Cape Ann by sea with Agawam Boat & Fishing Charters, offering private fishing and sightseeing cruises for up to six guests. Customize your adventure from Essex to Gloucester and Rockport, with options for beaches, lighthouses, sunsets, and more.
Second Glance Thrift Store
Shop Second Glance Thrift Store for unique finds, from clothing to home goods, while supporting The Open Door’s mission to fight hunger and serve the Gloucester community.
Windhover Performing Arts Center
Where the arts come alive under the summer sky — Windhover Performing Arts Center brings world-class dance, theater, and music to a breathtaking Rockport campus each season.
Niles Beach
Enjoy serene coastal views at Niles Beach, a quiet East Gloucester spot perfect for swimming, wading, kayaking, and sunsets, with soft sand and calm waters overlooking Gloucester Harbor.
Charles Fine Arts
Explore fine art and custom framing at Charles Fine Arts, a longtime Downtown Gloucester gallery featuring rotating exhibitions by local and regional artists.
Gloucester City Hall
Admire historic Gloucester City Hall, a landmark overlooking City Hall Plaza and Gloucester Harbor, offering a glimpse into the city’s civic history and classic New England architecture.
Plum Cove Beach
Enjoy a peaceful retreat at Plum Cove Beach, a sheltered, family-friendly cove with calm waters, scenic Ipswich Bay views, and opportunities for wading, beachcombing, and shallow-water diving.
Eastern Point Lighthouse
An active aid to navigation since 1832, Eastern Point Lighthouse marks the entrance to Gloucester Harbor — with the iconic Dog Bar Breakwater offering dramatic ocean views right next door.
Annisquam Harbor Lighthouse (Annisquam Light)
One of Gloucester's oldest lighthouses, the 41-foot brick Annisquam Light has marked the entrance to the Annisquam River since 1801 — best viewed from Wingaersheek Beach across the water.