Discover Gloucester’s Seaport Trail

Did you know that Gloucester, Massachusetts is the Oldest Seaport in America? The birthplace of the U.S. fishing industry, site of the first marine railway, home to the oldest continuously operating artists’ colony on Rocky Neck, and a hub of innovation for centuries, Gloucester’s Seaport has endless treasures to explore.

Gloucester, Cape Ann is a breath of fresh air in the fall season, with fresh seafood dishes, schooner sails, harbor cruises, whale watching, art, museums, foliage over the water, kayaking, uncrowded beaches, and a variety of places to stay. Gloucester has the largest lobster fishing fleet in the state of Massachusetts, and some years more lobsters are caught in the fall and early winter months than during the summer. Discover Gloucester’s Seaport Trail, rich with delectable seafood dishes, and lined with unique things to do and see.

Click here to download a printable brochure.

Catch-to-Table Fresh Seafood

1606 restaurant

1606 Restaurant & Oyster Bar

Located on the lobby level of Beauport Hotel Gloucester, the charming 1606 Restaurant & Oyster Bar offers an oceanfront experience showcasing New England coastal dining at its best. Celebrate modern American cuisine prepared with fresh, local ingredients by Executive Chef Jon McKechnie and his team. Featuring an upscale raw bar and international conservas, 1606 Restaurant offers a range of dishes, like their award winning Cape Ann Lobster Roll, Baked Haddock Casserole, or a perfectly cooked Dry Aged NY strip. The warm décor, seaside vistas and relaxed, upscale atmosphere provide a Cape Ann dining experience unlike any other.

Plan your experience and reserve online at

Magnolia 525 Tavern

Magnolia 525 Tavern

Magnolia 525 Tavern is a family owned and operated restaurant in Gloucester serving creative comfort food and rocking cocktails utilizing locally-sourced ingredients. The Tavern’s seafood is fresh off the docks daily from Fisherman’s Wharf & Halibut Jack Seafood. We procure locally sourced foods whenever possible. Located on Lexington Avenue in the Seaside Village of Magnolia, this dining hot spots is a mile from the historic Hammond castle and a short walk to the Magnolia Pier & beach. Visit to enjoy a drink from the bar, serving creative cocktails and craft beer on tap, or cozy in for dinner with friends surrounded by award-winning interior decor.

Peruse the menu and reserve online at

Mile Marker One

Mile Marker One

Dine at the water’s edge on the freshest seafood from our boats to your plates. Grass-fed beef, fresh inspired salads and sides, with excellent flavor for really “great” food. We pride ourselves off our reader reviews with super service and repeat customers. Have you heard about our cocktails? Come join us in the heart of our marina. Check out our “Wicked Tuna” boats from your table with both deck (heated and Igloos) and inside dining options and bars – open year round. Check our hours and you can join us for Breakfast too!

Check out the menu and book a reservation at

seaport grille

Seaport Grille

Seaport Grille at Cruiseport Gloucester is located directly on the harbor with two decks for classic waterview dining. Our menu offers a wide range of delectable cuisines made with the freshest ingredients including surf & turf options, classic American plates, Italian-inspired dishes, world-famous desserts and much more. Within the backyard of our restaurant lies the inner harbors of Gloucester, home to the oldest working waterfront in America. Join Seaport Grille all year long for $1.50 oysters on Wednesdays and our locally famous $24 Lobster Roll special on Thursdays! Seaport Grille: Come for the menu, stay for the vibe!

Find the menu, hours, and more at

woodmans of essex

Woodmans of Essex

“Best Waterfront Seafood Shack in America”-USA Today. Award-winning lobster rolls, gluten-free fried clams, seafood, and clam chowder. Family friendly, indoor and outdoor seating, and beautiful views of The Great Marsh. Voted “Most Iconic Restaurant in the Boston Area”-

Visit to check out the menu and plan your visit.

Explore the Waterfront

7 seas whale watch

7 Seas Whale Watch

Now through mid-October, 7 Seas Whale Watch offers daily trips to Stellwagen Bank National Marine Sanctuary aboard their high-speed whale watching vessel: the Privateer IV. This family-operated business has experienced captains, crew, and naturalists providing a great experience for passengers.

Reserve your space and learn more about the marine wildlife frequently sighted at

seaport grille

Beauport Cruiselines

Sitting in America’s oldest port, Beauport Cruiselines is the best way to get the perfect New England harbor experience. Surrounded by everything from local fishermen to whales and sailboats, it cannot get much more New England than aboard the Beauport Cruiselines. Take in the sweeping views and cool as you set sail around the gorgeous Gloucester Harbor while enjoying our award winning cuisine and dance away to live DJ entertainment!

Book your next night out at


Cape Ann Whale Watch

Cape Ann Whale Watch is the perfect excursion for you & your family, with tours running from April through October! There has been an abundance of whales & ocean wildlife on recent trips out to the feeding grounds. Give them a call at 1-800-877-5110 to book your next trip.

To learn more about the whales and trip schedule, visit:

hammond castle

Hammond Castle Museum

The Hammond Castle Museum is a dynamic museum offering tours, temporary exhibits, cultural events, and educational programming. Candlelight and spiritualism tours, concerts, movies, and more take place throughout the year. Built in the late 1920s as the home and laboratory of inventor John Hays Hammond, Jr, the museum’s architectural style is a mixture of a medieval castle, a Gothic cathedral, and a Renaissance-era French village set amongst Roman ruins. The museum is listed on the National Register of Historic Places and is not handicap accessible.

Find more information and plan your trip at

Lockwood Studios Still Edit

Lockwood Studios | Fine Art & Design Gallery

Artist Juliet Lockwood recently opened her gallery in collaboration with a number of local artists, showcasing fine art and design works in a series of ongoing exhibits. Lockwood Studios combine displayed, locally-curated artwork, educational workshops, a working art studio, and public space design concepts into a welcoming, beautiful space. Visit Lockwood Studios at 2 Eastern Ave and learn why Gloucester has been an arts hub for centuries.

Follow Lockwood Studios happenings and exhibitions on Instagram at

maritime gloucester

Maritime Gloucester

Maritime Gloucester is your chance to experience FISH in our Maritime Science Education Center, and SHIPS on our pier and in our galleries! All in one place for a day of unforgettable family fun! Exploring our campus is a walk through the past with an eye on the future!

Head to to plan your visit.

schooner adventure

Schooner Adventure

Schooner Adventure is a National Historic Landmark wooden fishing vessel built in Essex in 1926. She is the official flagship of Gloucester. After two successful careers; one as the highliner of the Gloucester fishing fleet and another as the Queen of the Windjammers in Camden, ME., she was returned to the people of Gloucester. Authentically restored, she sails today as an educational resource for visitors, students, and the community. Everyone is invited to join us for ticketed public sails, dockside tours, private charters, and educational programs.

Visit to learn more.


Schooner Lannon

Picture yourself relaxing on the deck of this pristine 65′ schooner as she sails out of historic Gloucester harbor. Join us for a sail and help the crew raise the sails, or just sit back and take in the sights and sounds of Gloucester’s coastline. An authentic experience that shouldn’t be missed!

Head to to learn more about this magnificent vessel.

Stay Seaside

beauport hotel exterior

Beauport Hotel

With a picturesque oceanfront location, upscale amenities and unforgettable hospitality, the 94-room Beauport Hotel Gloucester is the perfect getaway on the North Shore of Boston, MA just under 40 miles from the city. Sitting on the oldest fishing port in America, Beauport Hotel Gloucester offers the peak Cape Ann experience. All of our comfortable Gloucester, MA hotel rooms and suites offer spacious coastal elegance and are beautifully appointed with a soothing décor influenced by the colors of the ocean, sand, and sky.

Plan your stay at

cape ann motor inn

Cape Ann Motor Inn

Cape Ann Motor Inn sits directly on Long Beach, with rooms and kitchenettes overlooking the ocean, and views of Thacher Island’s twin lighthouses. The Inn offers free wifi, coffee and homemade pastry in the morning and we are pet friendly for an additional fee. Explore Gloucester by land and sea, then kick back and relax at this scenic, oceanfront Inn just steps from the sand.

Book your stay at

harborview inn

Harborview Inn

Overlooking Gloucester Harbor, this four-season bed & breakfast is perfect for experiencing America’s Oldest Seaport! The Inn is within walking distance to an array of dining options, boating excursions, museums, shops and attractions. Harborview Inn is located across from Stacy Boulevard, the Gloucester Fishermen’s Memorial, and Pavilion Beach, with picturesque waterfront views.

Check availability and plan your stay at

the hotel at cape ann marina

Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina is open year-round featuring on the water rooms with balconies overlooking beautiful saltwater marshes and marina on the beautiful Annisquam River, where you can walk to town and historic sites. Enjoy our newly renovated rooms and round out your stay with cocktails at the Hotel bar and dining at Mile Marker One Waterfront Restaurant (inside, outside deck and Igloos). Enjoy a unique “on vacation” destination by land or sea and take in all that The Hotel at Cape Ann Marina has to offer. Weddings and groups welcome.

Book your stay at

the vista motel

The Vista

The Vista offers breathtaking ocean views from every room, a stunning pool, and a serene atmosphere. Overlooking USA Today Reader’s Choice Award-Winning Good Harbor Beach, and a five minute drive from downtown, The Vista is ideally located to explore Gloucester’s Seaport.

Book your stay at

Funded, in part, by the Massachusetts Office of Travel & Tourism.