52 Best Weekend Trips and Getaways from Boston

Food & Wine

weekend trips getaways boston massachusetts new england


36. Warren, Vermont

Three hours, 30 minutes by car

Country Fare | Sure, Vermont has a ton of farms and food producers, but not all of the state is fruit stands and pick-your-own produce. Far from it: For a decidedly refined culinary expedition, hole up at Warren’s Pitcher Inn, where a world-class wine list and a tony dining room await. Staying there also puts you within striking distance of Hen of the Wood in Waterbury, where chef Eric Warnstedt creates stunning dishes from local meats, vegetables, and cheeses. Meanwhile, he’s also one of the forces behind spectacular al fresco dining events in conjunction with roving feastmakers Outstanding in the Field. How ’bout them apples?

92 Stowe St., Waterbury, Vermont, 802-244-7300, henofthewood.com. Stay: The Pitcher Inn, 275 Main St., Warren, Vermont, 802-496-6350, pitcherinn.com.


37. Morris, Connecticut

Two hours, 45 minutes by car

Get Some (Cooking) Class | New Englanders clamor for the mighty meals of Chris Eddy, the top chef at Winvian, a resort in the hills of western Connecticut. After all, he learned his trade from the masters—those gods du gastronomie, Alain Ducasse and Daniel Boulud. And to whom will Eddy, in turn, now pass along this wisdom? You, now that he has added cooking classes to the Winvian menu. Customizable coursework includes French and Mediterranean cuisine, presented in everything from weekend-long to six-week programs. Bonus: Design aficionados will adore the resort’s eclectic lodgings. One private cabin is made from a helicopter pit; another incorporates a tree house.

155 Alain White Rd., Morris, Connecticut, 860-567-9600, winvian.com.

38. New Castle, New Hampshire

One hour, 15 minutes by car

Wine Down | Around here, winter comes on like a brakeless freight train. What better reason to stay in and raise a glass? Every year in January and February, Wentworth by the Sea hotel hosts its seventh Winter Wine Festival, a series of vintners’ dinners, rare vintage tastings, and champagne receptions.

588 Wentworth Rd., New Castle, New Hampshire, 603-422-7322, wentworth.com.

39. Portsmouth, New Hampshire

One hour by car

Small Town, Big Eats | Sandwiched between Boston and Portland, Maine, most New Englanders see Portsmouth as a blip en route to more-memorable meals. Little do they know it’s home to a handful of trip-worthy restaurants. Start at Cava, a cozy tapas bar, for half-glasses of Spanish wines paired with bites of jamón serrano. For dinner, Moxy offers New American small plates (Fiddlehead Tomme churros, anyone?); Black Trumpet does superb seasonal upscale; and Jumpin’ Jays has the freshest fish around.

Stay: Ale House Inn, 121 Bow St., Portsmouth, New Hampshire, 603-431-7760, alehouseinn.com.

40. Québec City, Québec

Three hours by plane

French Class | Stepping off the three-hour flight from Boston (which includes a quick layover in Montreal), a first glimpse of Québec City inevitably comes with a dose of culture shock: It’s so French! But it’s so close! Get over it—there’s no time to spare. There are croissants to be eaten, café au laits to be sipped, poutine to be devoured. And within the stone walls of the old city, there are hours to be spent lolling at charming bistros and wondering why on earth you aren’t here every weekend.

Stay: Le Germain Hôtel Québec, 126 rue Saint-Pierre, Québec, 888-833-5253, legermainhotels.com.

41. South Burlington, Vermont

Three hours, 30 minutes by car

Ale Bonding | Peddling beers with names like Blind Faith, Lucky Kat, and Hocus Pocus, the Magic Hat Brewing Company has a knack for capturing the eccentricities of hop-based beverages. But at its home brewery just outside Burlington, the company truly lets loose, with group tours led by guides who are even quirkier than the suds they sell, as well as an in-house bar that specializes in experimental—and sometimes not-yet-ready-for-market—creations. (Pass the Apple Pie Ale, would you?)

Stay: Shelburne Farms Inn, 1611 Harbor Rd., Shelburne, Vermont, 802-985-8498, shelburnefarms.org.

42. Newport, Rhode Island

One hour, 30 minutes by car

Pier Pressure | The best reason to check out Newport’s Forty 1° North waterfront resort is its enviable vistas of Newport Harbor. But the food there is just as delicious. The property’s dockside dining option, the Grill, serves 28-day-dry-aged prime New York strip steak (and other forms of hifalutin beef). Christie’s is the funkier option, where futuristic-mod décor sets the scene for piquant fish tacos and tangy spare ribs.

351 Thames St., Newport, Rhode Island, 401-846-8018, 41north.com.

43. Amherst, Massachusetts

Two hours by car

Good Apples | Foment your fermentation ­knowledge at Franklin County’s annual CiderDays celebration. The sprawling festival always takes place the first weekend of November, and is awash in gourmet ciders from regional producers. Don’t miss out on the paired cheese-and-cider tasting.

Stay: Allen House Inn, 599 Main St., Amherst, 413-253-5000, allenhouse.com.

44. Montréal

One hour by plane

Dine & Dance | One part dance club and two parts restaurant, Montreal’s supper clubs house an evening’s worth of entertainment. See also: Garde-Manger, where chef Chuck Hughes feeds everyone in a tiny room that overflows with romance—chandeliers, champagne, and dancing. And while you’ll have no problem finding your next food coma in this city, one spot du moment worth checking out is Perles et Paddock: In a stunning space that was formerly a garage, this eatery trades socket wrenches and floor jacks for inventive cocktails and decadent brunches.

Stay: Le Petit Hôtel, 168 rue Saint-Paul Ouest, Montreal, 877-530-0360, petithotelmontreal.com.

45. Portland, Maine

Two hours by car

Catch the Buzz | Portland has been called America’s Foodiest Small Town, and no wonder: Everywhere you look, there’s something you must eat. A citywide obsession with sustainability flavors every meal. Hit one of the long-standing darlings, such as Hugo’s or Fore Street, and you won’t be disappointed. Meanwhile, other favorites, like Eventide (a James Beard Award–winning seafood haven) and bistro Five Fifty-Five, keep the city—and the rest of the country—buzzing.

Stay: Portland Harbor Hotel, 468 Fore St., Portland, Maine, 207-775-9090, portlandharborhotel.com.

46. Long Island, NY

Two hours by car to ferry

Grape Escape | It’s not Napa, but the North Fork region of Long Island has more than 40 vineyards ranged along a scenic roadway of farms, antiques stores, and B & Bs. The best offerings, such as Old Vines merlot by Lenz Winery, compare positively with French Pomerol, while chardonnays by the likes of Macari and Pellegrini have a distinct terroir.

Stay: The Stirling House Bed and Breakfast, 104 Bay Ave., Greenport, New York, 800-551-0654, thestirlinghouse.com. See the schedule for the Cross Sound Ferry in New London, Connecticut, at longislandferry.com.

47. Northampton, Massachusetts

Two hours by car

Raising the Bar | A town this size is lucky to have so much as one bar. And yet NoHo is blessed with nearly a dozen watering holes, with something to suit every drinker. Beer snobs congregate at the Dirty Truth, which has 40 brews on tap. Beer slobs like Ye Ol’ Watering Hole and its infamous Beer Can Museum. And hipsters hit the Iron Horse, a rock club that books bigtime bands that often skip Boston altogether.

Stay: Hotel Northampton, 36 King St., Northampton, 800-547-3529, hotelnorthampton.com.

48. Ogunquit, Maine

One hour, 30 minutes by car

The Epicure’s Enclave | In their frantic dash north, Portland-bound gastronauts pass within a mile of this undersung food-lover’s haven. Their loss. It’s a dining landscape far more cosmopolitan than its beachside setting would suggest. To wit: torchon of foie gras at Northern Union; handmade gnocchi at No. Five-O Shore Road; and, of course, Bailey Island blueberry tart at M.C. Perkins Cove. Portland who?

Stay: Beachmere Inn, 62 Beachmere Place, Ogunquit, Maine, 800-336-3983, beachmereinn.com.

49. Westerly, Rhode Island

Two hours by car

A Shore Thing | The seven impeccable rooms (some with an ocean view) are enough to warrant a stay at Langworthy Farm, but the charming B & B also happens to be a small-batch winery that produces 11 vintages. Swing through in October, when owners Joe and Gail Sharry solicit help with their grape harvest.

308 Shore Rd. (Rte. 1A), Westerly, Rhode Island, 401-322-7791, langworthyfarm.com.

50. Castine, Maine

Four hours, 30 minutes by car

Organically Delicious | At a time when even hot dog stands claim locavore cred, the restaurants along the Blue Hill Peninsula are the real deal. Currently, the most exciting plates are at Arborvine, where these farm-to-table fanatics serve up such coastal flavors as Penobscot-raised Bagaduce oysters with sake mignonette and T-bone steaks sourced from neighboring Blue Hill Blondes.

33 Tenney Hill, Blue Hill, Maine, 207-374-2119, arborvine.com. Stay: Pentagöet Inn, 26 Main St., Castine, Maine, 207-326-8616, pentagoet.com.

51. Vermont

Three hours by car

Cheese Wizard | Cheddar may get all the hype, but it’s only a tiny slice of what’s represented along Vermont’s Cheese Trail. The 280-mile loop spans the state, and is studded with farmsteads offering tours, with points of interest including Grafton Village and Jasper Hill Farm. A weekend of roaming will keep you sated with everything from organic ricotta salatas to raw-milk blues. And, of course, glorious cheddar.

vtcheese.comStay: Hawk Inn and Mountain Resort, 75 Billings Rd., Plymouth, Vermont, 800-685-4295, hawkresort.com.

52. Nantucket, Massachusetts

One hour by plane

Reserve Yourself | Set foot to cobblestone anytime June through August on Nantucket, and your chances of getting into one of the island’s hot-spot restaurants are as good as Ahab’s chance of landing Moby. But go in shoulder season, and you’ll find plenty of tables at ultrachic spots like the Pearl, Lola 41°, and American Seasons—all of which stay open through December.

Stay: The Sherburne Inn, 10 Gay St., Nantucket, 508-228-4425, sherburneinn.com.


By Matthew Reed Baker, Michael Blanding, Christy DeSmith, Donna Garlough, Alexandra Hall, Jolyon Helterman, Brittany Jasnoff, Rachel Levitt, Jason Schwartz, and Anne Vickman

Note: This guide was updated July 2018.

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