14 Best Restaurants in Side Trips from Boston, Massachusetts

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.

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.

This fine-dining restaurant, located in the Concord Depot, offers New American cuisine, with much of the food on the plate coming from nearby local farms. Friendly and knowledgeable servers can help you navigate the menu, which changes with the seasons, along with what’s available at the time.

The Concord outpost of the long-running Bedford Farms Ice Cream shop offers just as many tasty, locally made ice creams. "Always Making" flavors include chunky chocolate pudding, green monster, and black raspberry, but there is also a list of "Sometimes Making" flavors, sorbets, and sherbets. You can also order custom ice cream cakes and pies with advance notice.

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.

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.

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.

Housed in a 200-year-old building that was once a bank—Ledger takes its name from the massive amount of banking ledgers found in the building—today diners enjoy a modern-day spin on traditional 19th-century dishes, especially live-fire cooking. Grab a cocktail while checking out the multitude of original features incorporated into the restaurant, including deposit boxes and a huge safe that serves as the restaurant’s walk-in refrigerator. Grab a peek of the private dining room, where the wooden chair rails are sourced from pews in an old church near Boston Common.

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.

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.

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.

This contemporary restaurant offers bistro-style chicken, roast cod, and steak frites, perfect for the late-night crowd (it's open until midnight during the summer). There is usually live music on Thursday evening. There is also a raw bar and sushi selection. Look for the signature martini glass over the door.

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.