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Chatham Bars Inn
Photograph: Courtesy Chatham Bars InnChatham Bars Inn

The best weekend getaways from Boston

Escape from the city with these stress-free weekend getaways, including jaunts to Maine and the Berkshires.

Olivia Vanni
Written by
Olivia Vanni
&
Eric Grossman
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Whether it’s the dog days of summer or the bone-chilling winter, sometimes you just need to get the hell out of Boston for a bit. Sure, taking one of the best day trips out of the city might be good for a temporary fix, but there are times when a single day away will be no match for your wanderlust. That's when you should turn to this list of easy weekend getaways, where you can get a real change of scenery and end up feeling refreshed. Once you’re back in town, you can go right back to your normal weekday routine of hitting up the best museums, listening to some stellar live music and dining out at the hippest restaurants in Boston.

RECOMMENDED: Full guide to the best things to do in Boston

Best weekend getaways

Kennebunkport, ME
Photograph: Courtesy The Boathouse

1. Kennebunkport, ME

Home to the Bush compound, this seaside town has plenty of attractions for the hoi polloi as well: beach walks (take the Parson’s Way Shore Walk to spy on the homes of One Percenters), bike trails, boutiques and one of the most lauded lobster rolls in New England, courtesy of The Clam Shack (opt for mayo and melted butter to really bring it home).

Eat at: Earth at Hidden Pond (354 Goose Rocks Rd; 207-967-6550) highlights seasonal and local ingredients, including herbs and vegetables grown just behind the restaurant. Chez Rosa (2 Ocean Avenue Dock Square; 207-204-0183) elevates New England's natural bounty with its classically French preparations. Drink in the good life with a pre-dinner cocktail at The Tides Beach Club (254 Kings Hwy; 855-632-3224).

Stay at: The Boathouse (21 Ocean Ave; 207-967-8225) brushes up against the Kennebunk River, which is easily viewed from your sleek room’s oversized windows. 

Bad for: Solitude. Unless you bike outside of town, this area is a tourist magnet once temperatures rise above 60 degrees.

Stowe, VT
Photograph: Courtesy Stowe Mountain Lodge

2. Stowe, VT

New England is awash with winter resort towns, but we most love those areas that celebrate four-season recreation. Come summer, Stowe swaps out skiing for hiking, golfing, mountain biking and kayaking. Bonuses include swimming hole visits and scenic drives up the squiggly Auto Toll Road.

Eat at: Plate (91 Main St; 802-253-2691) combines California cuisine with Vermont-sourced ingredients. Take the gondola up to Cliff House (5781 Mountain Rd; 802-253-3665) and enjoy a bottle of wine on the outside deck before hiking down afterward.

Stay at: Stowe Mountain Lodge (7412 Mountain Rd; 802-253-3560) manages to feel homey and warm (also dog-friendly!), despite its luxury amenities. Added perk: It's also dog friendly, so your canine companions can come stay on vacay.

Bad for: Indoor folk. 

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3. Portland, ME

When Boston chefs started leaving our city to open restaurants in Portland, it was further proof that the Forest City had arrived as a culinary destination. The city’s walkability and charming brownstones will provide ample fodder for all of your wildest pied-à-terre fantasies.

Eat at: Everywhere, basically:Eventide Oyster Co. (86 Middle St; 207-774-8538) for oysters; Portland Hunt and Alpine Club (75 Market St; 207-747-4754) for cocktails; Central Provisions (404 Fore St; 207-805-1085) for the locavore meal of the moment; Duckfat (43 Middle St; 207-774-8080) for fries, poutine and a milkshake when you're hungover the next day.

Stay at: The Press Hotel (119 Exchange St; 800-971-2000), former home of the Portland Press-Herald, carries on the print tradition with newspapered walls, letterpress carpeting and leather desk chairs. 

Bad for: The seafood-averse. If you’re not there to inhale oysters and lobster rolls, you might want to rethink your plans.

The Berkshires, MA
Photograph: Scott Barrow

4. The Berkshires, MA

In need of fresh air and an espresso shot of culture? The Berkshires have you covered with museums, concerts, legendary authors' homes, botanical gardens, hiking and whitewater rafting. It’s well worth tangling with the Tanglewood crowds.

Eat at: Methuselah Bar and Lounge (391 North St, Pittsfield; 413-347-2888) is focused on organic wines and craft beers, pairing them with funky, reimagined American fare, tacos and Korean-inspired dishes. The Prairie Whale (178 Main St, Great Barrington; 413-528-5050), from man of the world and Brooklyn expat Mark Firth, has brought a little rock-n-roll dining to the countryside.

Stay at: Wyndhurst Manor & Club (55 Lee Rd, Lenox; 877-781-7125), an opulent former mansion, gives you a taste of the luxe life with its expansive estate grounds, golf course and spa.

Bad for: Real estate lust. It’s hard not to peruse the single-family listings and wonder why the hell you’ve committed to city living. 

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Portsmouth, NH
Phototograph: Courtesy Greater Portsmouth Chamber of Commerce

5. Portsmouth, NH

Donation-based outdoor concerts, art galleries, riverside farm-to-table dining and a bookstore that serves beer and wine—all an hour’s distance from Boston.

Eat at: Moxy (106 Penhollow St; 603-319-8178) from James Beard nominee Matt Louis does American tapas like you’ve never seen (i.e. pork belly bites and mini red hots).

Stay at: Ale House Inn (121 Bow St; 603-431-7760), a former brewery with brick-walled rooms, in-room iPads and a complimentary bottle of Smuttynose upon check-in. 

Bad for: Shopping. Portsmouth’s retail scene is still a work in progress.

Providence, RI
Photograph: Courtesy The Dorrance

6. Providence, RI

When did our southern neighbor become so grown up? Providence is now a bonafide go-to destination, thanks to its WaterFire performances, concerts and serious dining scene. “Creative Capital” indeed.

Eat at: CAV Restaurant (14 Imperial Pl, 401-751-9164) is part-eatery, part-antiques shop, serving its bistro bites in a truly stunning setting. Drinks at The Dorrance (60 Dorrance St; 401-521-6000) will transport you back to the Roaring Twenties.

Stay at: The Dean Hotel (122 Fountain St; 401-455-3326), a 51-room boutique, has brought a new level of hipsterdom to the downtown area. 

Bad for: Peace and quiet. You’re trading one city for another—albeit on a smaller scale. 

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Chatham, MA
Photograph: Courtesy Chatham Bars Inn

7. Chatham, MA

The Cape is a no-brainer, but where to stake your claim? We’ve long migrated towards the inimitable charms of Chatham, where the homes will make you drool, the town center is walkable and crammed with cute boutiques, and the seafood is hauled in just offshore. 

Eat at: Impudent Oyster (15 Chatham Bars Ave, 508-945-3545) offers innovative spins on classic seafood dishes and a lively bar inside a former church.

Stay at: Chatham Bars Inn (297 Shore Rd; 508-776-6700) is the ne plus ultra of Cape retreats for good reason: The cabana’d beach alone earns the resort its mythic reputation—and justifies the indulgence.

Bad for: Those who covet. You’ll wish you were born into old money. 

Block Island, RI
Photograph: Shutterstock

8. Block Island, RI

Nantucket and the Vineyard get all the island love, but this Rhode Island retreat, located just 13 miles offshore, is just as deserving. It boasts the same natural-shingled charm of its northern brethren—without the red shorts and pretension. Nature lovers, rejoice: Forty percent of the island is conservation land, accessible only by bike or foot.

Eat at: Eli’s (456 Chapel St; 401-466-5230), a tiny favorite among locals, serves fresh, American comfort food with a slightly Asian twist. Before heading back to the ferry, grab gourmet sandwiches from Three Sisters (443 Old Town Rd; 401-466-9661).

Stay at: Spring House (1401 Ocean Ave; 732-776-6700), the island’s oldest hotel (Twain stayed there), entices with Adirondacks and a wraparound veranda overlooking the water. 

Bad for: Narragansett haters. To drink cheap, you’ll drink ‘Gansett. Period. 

See the best road trips in America

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