Cabot’s Ice Cream & Restaurant
743 Washington St., Newton
Cabot's, located in the Boston suburb of Newton, has long been a popular neighborhood spot, though many Bostonians make the trip, too. A family-run restaurant serving diner-esque comfort food (including all-day breakfast), Cabot's is designed like an old fashioned ice cream parlor: white-and-black tile floor, red booths, rotating counter seats, paper placemats. They have a noteworthy array of ice cream sundae options (70-plus favors and 35-plus toppings), along with the kind of indulgent classics that never do you wrong: chocolate malteds, banana boats, Belgian waffles topped with a few scoops, root beer floats. They also do cakes, pies, cupcakes, and sundae catering.
33 N. Sq., North End
North End is a fun destination for dinner, specifically for Italian food, where your best bet is Carmen Trattoria, which has a lovely, low-key, exposed brick dining room. It’s a good idea to call ahead for a reservation. If you can, save room, and walk to legendary Mike’s Pastry after dinner. The cannolis get all the attention, but the lobster tails are really where it’s at. (Side note: Another popular spot for old-school Italian in Boston is Giacomo’s, which has a location in the North End, as well as one in South End, and a third outside of the city.)
Moby Dick’s Restaurant
3225 Rte. 6, Wellfleet
Just-caught seafood is Cape Cod’s claim to fame and if you’re only here for a few days, having a turkey sandwich for lunch just doesn’t feel right. Moby Dick’s, which has been family-operated since the 80’s, has the quaintness of a clam shack and the menu of a full-on restaurant, meaning that you can order an oyster platter, steamed lobster, and grilled fish in addition to the basics like chowder and fried clams. It’s also one of the few spots around with a respectable gluten-free offering.
513 Tremont St., South End
Pizza and ice cream play equal starring roles at Picco in the South End, although it should be noted that they have a great draft beer list, as well. The pizza is wood-fired with Picco's signature well-done crust, and the ice cream list covers all the essentials from plain dishes and cones to brownie sundaes, plus some desserts geared specifically to the 21-and-over crowd, like The "Adult" Ice Cream Soda: raspberry Belgian Lambic poured over vanilla ice cream. There's a casual outdoor patio, along with a small interior that reads like a cozy bistro.
The Glass Onion
37 N. Main St., Falmouth
In the land of never-ending seafood, this fine-dining spot in Falmouth is where you go for a really great steak, a veggie-rich salad, or house-made ravioli (though there is a good chance that it will be stuffed with lobster). With its pane-glass windows and exposed-beam ceilings the setting is both romantic and unintimidating—to up the wooing factor, spring for a bottle from the excellent wine list.
1704 Washington St., South End
While Boston isn’t known for its tapas scene (though there is more than one option in the South End), Toro serves truly good Barcelona-style dishes using locally sourced ingredients. A collaboration between noteworthy Boston Chefs Ken Oringer and Jamie Bissonnette, Toro is open for dinner every night (no reservations), weekday lunches, and Sunday brunch. Big on sustainability, Toro composts all biodegradable waste, makes their take-out products from renewable/biodegradable materials, and serves organic, biodynamic wines and spirits.
Union Oyster House
41 Union St., Downtown
Housed in a pre-Revolutionary building and open since 1826, Union Oyster House is a little touristy but it makes sense why: It’s iconic Boston and the clam chowder is out of this world. Go at least once—it’s located on the Freedom Trail so you can stop in along your walk. Bonus: It’s also steps from the famous New England Aquarium (which is right on the water), where littles can check out a multistory tank, a gorgeous penguin sanctuary, and up-close-and-personal seals
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