Curator’s statement
A quiet coastal town 45 minutes north of Boston, Gloucester tends to get overlooked as a destination for non-locals, and that is part of what makes it such a special destination. As a girl born and raised in New York City, coming to a town where everyone knows each other is a surreal experience. It gives the city such a warm and welcoming vibe that, coupled with the stunning natural beauty, makes this a repeat destination. Come for the beach and views, stay for the dining and the people. Gloucester is part of what makes up "the other Cape," Cape Ann, along with the towns of Essex, Manchester-by-the-Sea and Rockport. It is America's oldest seaport, so naturally their seafood is top-notch. Known for their fishing - it is the filming location for Wicked Tuna - beaches, and whale watching, it’s the perfect destination if you’re looking for Cape Cod vibes, with way less people.
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Where to stay in Gloucester
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Things to do in Gloucester
Local activities
Hammond Castle: A truly unique attraction, it almost feels like it was picked up and dropped off exactly as it is from somewhere in Europe.
The Cut: A bar, restaurant and live music venue, The Cut always has something going on. Catch drag shows or performances from up-and-coming artists while you dine.
Good Harbor Beach: A small, well-kept beach with great swimming conditions.
Sail on a Schooner: The Lannon is one of the most relaxing ways to spend your day. Sail on a classic schooner and catch a sunset on the ocean.
Festivals
St. Peter's Fiesta: This festival happens every year on the last weekend in June and is the city's unofficial start of Summer. The beachside carnival, the Greasy Pole competition, the Seine boat race: this is a Gloucester tradition that goes back nearly 100 years. A one-of-kind experience.
Schooner Festival: This festival occurs every Labor Day Weekend, and one of my fondest memories is sitting on the porch of the Harborview Inn, watching the parade of boats pass by as the sun warmed my skin & the light ocean breeze blew by.
Day trips
Rockport
Boston
Places to eat & drink in Gloucester
Causeway: A bit off the beaten path, the Causeway is worth stepping away from Main St. Serving classic Italian and seafood dishes, they are huge portions, but more importantly, it is also delicious.
Two Sisters: My personal favorite spot for breakfast or lunch! If you're looking to sit and dine, they have tasty and large portions. if you need something to grab and go, they also have homemade pastries that are sure to satisfy.
Blue Collar Lobster: Sit outside by the water while dining on fresh lobster rolls. The outdoor dining area is also pet-friendly, so bring along your dog so everyone in the family can enjoy the ocean breeze!
SushiSangLee: Tucked away inside a wine shop, this 8-seat sushi bar is the best meal I've had in Gloucester. Chef Sang Lee worked in Boston and New York City before settling here in Gloucester. As a tribute to his home, Chef uses local fish caught in Gloucester as much as possible in his menus.
Holy Cow Ice Cream: Holy Cow's ice cream is award-winning, and for good reason. They have their core menu, which is always around, but they also regularly roll out limited time flavors so there is always something new to try. As a coffee lover, their Cold Brew Oreo is incredible! Their Ritzy AF flavor is probably their most popular, but you really can't go wrong.
Castaways Vintage Cafe: Part vintage shop, part coffee shop, Castaways serves the best cold brew I've had in Gloucester and is always stocked with fun vintage items as well as their own branded merch. Grab a coffee and spend some time browsing their racks.
Travel Advisor
Jen Luu
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This guide is a part of our ongoing series on travel to Massachusetts. For more travel tips, check out Fora Advisor Isabel Smallman's guide, A Great Alternative to the Cape: Exploring North Shores' Gloucester, MA.