Gloucester, Massachusetts

America’s oldest seaport offers bountiful seafood, surf, and local flavor.

Credit: Chris McIntosh
  • Current
    Weather

Clouds & 55°

  • When to
    Visit

Summer or Fall

  • Population
     

30,291

  • Founded
     

1642

By Chelsea Bell

About an hour north of Boston, at the end of Route 128, Gloucester offers breathtaking harbor views and plenty of seaside activities. The North Shore city—celebrating its 400th birthday in 2023—is known for its fishing fleet, historic artist community, and as the location of the Oscar-winning film, Coda. The Gloucester food scene is very much shaped by the vibrant maritime culture (think tuna, haddock, lobster, and shellfish galore), but also by the Sicilian and Portuguese fishermen who immigrated here. Whether you’re visiting Cape Ann for the day, a weekend, or staying indefinitely, here are some local spots to explore while in Glosta.

About an hour north of Boston, at the end of Route 128, Gloucester offers breathtaking harbor views and plenty of seaside activities. The North Shore city—celebrating its 400th birthday in 2023—is known for its fishing fleet, historic artist community, and as the location of the Oscar-winning film, Coda. The Gloucester food scene is very much shaped by the vibrant maritime culture (think tuna, haddock, lobster, and shellfish galore), but also by the Sicilian and Portuguese fishermen who immigrated here. Whether you’re visiting Cape Ann for the day, a weekend, or staying indefinitely, here are some local spots to explore while in Glosta.

Caffe Sicilia

Credit: Chris McIntosh

Caffe Sicilia
Take yourself back in time at Caffe Sicilia, where you might hear more Sicilian dialect than Boston accents. This quintessential Italian bakery is located in downtown Gloucester’s historic West End—an excellent place for a morning cappuccino and cornetti or mid-afternoon espresso and biscotti. Try the Cassatine Cake (a traditional Sicilian ricotta sponge cake), and don’t leave without an assortment of sweet treats like rainbow layer, Champagne, and lemon ricotta cookies; cannoli; and gelato. Right across the street, Virgilio’s Bakery is home to the bread of the fishermen, featuring the best Italian sandwiches to take away made on famous St. Joseph’s semolina rolls. Take me there.

Credit: Chris McIntosh

Willow Rest
This historic market on the Annisquam River is a happy place for residents of Gloucester’s Riverdale and Annisquam communities. In 2009, chef Melissa Donati reimagined Willow Rest as a neighborhood restaurant with homestyle cafe fare: baked goods, prepared foods, and groceries. Stop in for generous portions for breakfast and lunch, beginning with breakfast burritos, omelets, French toast, and pancakes. Eat in or carry out Donati’s signature sandwiches (named after Cape Ann landmarks) and brick oven-baked focaccia with toppings like roasted potatoes, caramelized onions, jalapeños, and bacon. While you wait for your order, peruse the selection of artisan gifts, local crafts, and seasonal provisions so you can be fully stocked for whatever fun awaits. Take me there.

Credit: Chris McIntosh

Pastaio Via Corta
Pasta lovers can rejoice at chef Danielle Glantz’s Pastaio via Corta. This award-winning specialty shop, now located on Main Street, features organic pastas handmade with stone-ground wheat, available fresh or dry, and a variety of homemade sugos (sauces) and pestos. Pastaio’s Ravioli are one of the best dinner party hacks: available Thursdays and Saturdays, these pasta pillows are filled with seasonal, locally sourced ingredients and so easy to prepare at home. In addition, you’ll find an outstanding selection of authentic Italian specialty food items, from Umbrian olive oil to Sicilian tinned fish, and a wall of all-natural Italian wines along with traditional apéritifs and amari. This inviting store is the real deal. Take me there.

Credit: Chris McIntosh

Turner’s Fresh Seafood Market
Instead of waiting at the docks for the day boats to arrive for the freshest seafood, just go to Turner’s. Located a few blocks away from the hustle and bustle of Main Street and the Gloucester waterfront, this 70-year-old seafood company’s slogan is “anything fresher still swims.” Expect to find local tuna to bring home and cook on the grill and the best choice for baked haddock. Additionally, the famous Fish ‘n’ Chips service is available for takeout any day of the week beginning at noon. You might as well indulge in shrimp cocktail, crab cakes, oysters Rockefeller, and chowder, too. Take me there.

Credit: Chris McIntosh

Alexandra’s Bread
Alexandra’s is one of Gloucester’s hidden gems, featuring some of the best bread, scones, cookies, and brownies to be found on the North Shore. Started more than 20 years ago by married couple Alexandra Rhinelander and Jon Hardy (formerly of Brookline’s famous Clear Flour Bread), this family operation is beloved by anyone who discovers it. Offerings include baguettes, cobbles (round loaves), focaccia, Green Devils (olive bread), cranberry scones, chocolate chip cookies, and more. Call to place your order in advance, as items can sell out quickly. Pro-tip: their breads and baked goods also freeze well if you want to stock up. Take me there.

Credit: Chris McIntosh

1606 at the Beauport Hotel
After a full day of beaching, boating, shopping, and exploring, unwind with a drink on the deck at Gloucester’s Beauport Hotel. Beauport’s 1606 Restaurant and Oyster Bar looks out onto the picturesque Gloucester harbor with great views of Ten Pound Island, the breakwater, and even Boston on a clear day. A beautifully designed, indoor wrap-around raw bar also provides prime seats for taking in the seaside vistas. The 1606 offers a variety of local craft brews on tap accompanied by wines and cocktails alongside small plates like curry mussels and cheese boards, lobster rolls, classic entrees like Baked Haddock Casserole, and more. Take me there.

Credit: Chris McIntosh

Short & Main
For those craving wood-fired pizza and a raw bar, Short & Main is a favorite Gloucester watering hole serving up locally sourced food in a convivial environment. The ownership trio—formerly of the famed, now-closed Market Restaurant—opened Short & Main in 2013, specializing in oysters, crudo, meatballs, and an assortment of al forno daily specials. The craft cocktails are inventive and delicious, and a bespoke wine list spotlights minimal intervention Italian and Italian-influenced producers. Take me there.

Credit: Talise

Talise
If you’re looking for a farm-to-table, waterfront dining experience, look no further than Talise. Opened in 2020 by Joshua and Ariel Smith, in the charming hamlet of Annisquam’s Lobster Cove, it’s truly a dining destination. With the menu changing daily to spotlight local farmers and fishermen, there’s always something new and tempting, from dressed oysters and pasta dishes to house-made desserts. Enjoy a thoughtfully curated beverage list, including small-production, artisanal wine and a great selection of local craft beer and ciders. Take me there.

Credit: Chris McIntosh

Tonno
Tonno translates to “tuna” in Italian, and it’s also a restaurant offering up some of the freshest catch anywhere. Whether dining inside the historic building or outside under the covered patio, Tonno is the perfect setting for dinner out on the town. It’s also one of the few spots in Gloucester which offers Sunday brunch, with tasty offerings from Poached Lobster Benedict to Brunch Flatbread. Don’t leave without sampling chef Anthony Caturano’s Tonno Tartare, arancini, or homemade pastas. The beverage list emphasizes Italian and California wine selections and features Martinis and Spritzes that are too good to resist. Take me there.

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