Side Trips from Boston Restaurants

We’ve compiled the best of the best in Side Trips from Boston - browse our top choices for Restaurants during your stay.

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  • 1. Clam Box of Ipswich

    $$

    Shaped like a giant fried-clam box, this small roadside stand is the best place in the region to sample Ipswich's famous bivalves. Since 1935 locals and tourists have been lining up in droves for clams, oysters, scallops, and onion rings.

    246 High St. (Rte. 1A), Boston, Massachusetts, 01938, USA
    978-356–9707

    Known For

    • Fried seafood
    • Friendly service
    • Long lines

    Restaurant Details

    Rate Includes: Closed late Nov.–Feb., $10 credit card minimum, Reservations not accepted
  • 2. Woodman's of Essex

    $$

    According to local legend, this is where Lawrence "Chubby" Woodman invented the first fried clam back in 1916. Today this sprawling wooden shack with indoor booths and outdoor picnic tables is the place for seafood in the rough. Though it's in Essex, it's a quick drive from Gloucester and worth getting a to-go order to take to the beach. For fun, you can get into a lively discussion with a local over whether clam bellies or strips are the better choice.

    121 Main St. (Rte. 133), Boston, Massachusetts, 01929, USA
    978-768–2559

    Known For

    • Fried clams
    • Open year-round
    • The popular "down-river" lobster combo plate
  • 3. Brackett's Oceanview Restaurant

    $$

    Enormous windows in this quiet, homey restaurant offer excellent views across Sandy Bay, along with plenty of chowder, fish cakes, lobster, and other seafood dishes. While the restaurant is only open seasonally, next door is Brackett's café, Brother's Brew Coffee Shop, which is open year-round and serves breakfast.

    25 Main St., Boston, Massachusetts, 01966, USA
    978-546–2797

    Known For

    • Local seafood
    • Every table has a waterfront view
    • Great downtown location

    Restaurant Details

    Rate Includes: Closed Columbus Day–mid-Apr.
  • 4. Finz Seafood & Grill

    $$$

    This contemporary seafood restaurant on Salem Harbor treats patrons to prime canal views. There is an extensive sushi and sashimi menu, plus lots of other seafood favorites, including sesame-crusted tuna and steamed lobster. Burgers and steaks are also available for meat eaters. Nab a seat on the outdoor deck when the weather's fine and eat practically among the boats.

    76 Wharf St., Boston, Massachusetts, 01970, USA
    978-744–8485

    Known For

    • Outdoor seating
    • Classic New England seafood
    • Large sushi menu
  • 5. Haute Coffee

    $

    Stop in for freshly brewed coffee and homemade baked goods, like banana bread, granola bars, and cinnamon buns, at this cozy spot. At lunch, enjoy the soup du jour and a selection of sandwiches. In nice weather, enjoy your food outside on the patio.

    12 Walden St., Boston, Massachusetts, 01742, USA
    978-369–9900

    Known For

    • Creative pastries
    • Coffee ground and brewed to order
    • Gluten-free and vegan options

    Restaurant Details

    Rate Includes: Closed Mon.
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  • 6. Main Streets Market & Cafe

    $$

    Cyclists, families, and sightseers pack into this brick building, which was used to store munitions during the Revolutionary War. Wood floors and blackboard menus add a touch of nostalgia, but the extensive menu includes many classic dishes, including mac and cheese, fish and chips, and steamed mussels. Breakfast offerings, served all day, include a variety of eggs Benedicts, a breakfast burrito, and omelets. At lunch, try the house-made chili or a variety of salads.

    42 Main St., Boston, Massachusetts, 01742, USA
    978-369–9948

    Known For

    • Open early for breakfast
    • Dog-friendly patio
    • Full bar

    Restaurant Details

    Rate Includes: No dinner Sun.–Wed.
  • 7. Passports

    $$$

    In the heart of downtown Gloucester, Passports serves a modern take on classic New England seafood. Whether you sit at the bar or a table, you'll be served delicious complimentary popovers to start. The house haddock is a favorite here, with other options like lobster and paella on offer. There's always local art hanging on the walls for patrons to buy.

    110 Main St., Boston, Massachusetts, 01930, USA
    978-281–3680

    Known For

    • Lively atmosphere
    • House haddock
    • Great, central location
  • 8. The Blue-Eyed Crab

    $$$

    Grab a seat on the outside deck overlooking the water at this friendly, somewhat funky (plastic fish dangling from the ceiling), Caribbean-inspired eatery. Enjoy fruity cocktails on the patio, or hang out in the colorful dining room. Start with thick crab bisque full of hunks of floating crabmeat or coconut shrimp with green mango chutney. Dinner entrées include Caribbean fish stew, jerk chicken, and the Cajun mahi fish tacos.

    170 Water St., Boston, Massachusetts, 02360, USA
    508-747–6776

    Known For

    • Views of the water
    • Funky decor
    • Tropical cocktails
  • 9. The Landing

    $

    Decorated in nautical blues and whites, this pleasant restaurant sits right on Marblehead harbor, with a deck that's nearly in the water. The restaurant offers classic New England fare like clam chowder and broiled scrod, and serves brunch on Sunday. The pub area has a lighter menu and a local feel.

    81 Front St., Boston, Massachusetts, 01945, USA
    781-639–1266

    Known For

    • Waterside dining
    • Classic New England menu
    • Local feel
  • 10. Virgilio's Italian Bakery

    $

    Since 1961, this bustling Italian bakery and deli has been making fresh breads and rolls, serving some of the tastiest sandwiches around. One of the shop's claims to fame is the now-famous Saint Joseph Sandwich, made with their Italian rolls stuffed with Italian deli meats, olive oil, and oregano. Pick up one (or two), along with other grocery items, before heading to the beach for a picnic.

    29 Main St., Boston, Massachusetts, 01930, USA
    978-283–5295

    Known For

    • Family-owned
    • Tasty prepared foods
    • Busy in summer

    Restaurant Details

    Rate Includes: Closed Sun.

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