20 Best Weekend Getaways in New England

With prettier-than-a-picture countryside, cliff-lined coasts under the watchful beams of centuries-old lighthouses, and countless small towns to stumble upon, New England is a region that merits a lifetime of getaways, weekend or otherwise. Whether you’re looking for a quick escape from the city or a romantic trip, here are 20 of the best weekend getaways in New England.

1. Block Island, Rhode Island

Towering bluffs, plains filled with native shrubs, and a grand Victorian-style hotel: This really could be England. The cedar-shingled saltbox houses are what clue you back to the fact that we’re in New England, not some wind-swept corner of the U.K. This may be a quintessential seaside getaway, but a trip here is just as much about cruising down country lanes and walking through open heathland as it is visiting the beach.

2. Mad River Valley, Vermont

Below the famous Sugarbush and Mad River Glen ski areas, the Mad River Valley is a particularly pretty nook of Vermont. And that’s on top of a surprisingly glam history (Sugarbush was once dubbed “Mascara Mountain” by Vogue due to all the fashionable model types frequenting its slopes). The skiing’s still good around these parts, but there’s also fun off-the-slopes stuff like mountain biking, farm-stand shopping, and summer concerts.

3. Nantucket, Massachusetts

Reverence for this 50-square-mile fleck off the coast of Massachusetts runs deep, especially when it comes to summer getaways. But forget the cars and chain restaurants that clog your typical beach scene. Instead, hop on a bike or island shuttle to visit historic lighthouses (the still-in-use Brant Point goes back to 1746!), grand homes built for whaling captains, and laid-back beaches. Refuel every few hours with a lobster roll or perfectly prepared bay scallops.

4. Newport, Rhode Island

Fans of HBO’s Gilded Age owe themselves a trip to Newport, the summer vacay spot of choice for the late-19th-century elite. Take a stroll down the Cliff Walk to see Newport’s lavish mansions on one side and the Atlantic Ocean crashing against rocks on the other. The 3.5-mile path works up an appetite, so you’ll be ready to feast like a Vanderbilt: do the (BYOB!) brunch at Cru Cafe or go big with lobster mac ‘n’ cheese at local landmark, Brick Alley Pub.

5. Sugar Hill, New Hampshire

City folk looking for a slow pace and gorgeous scenic views find lots (and lots) to love in Sugar Hill. The sight of brilliant fall colors or fields blanketed in deep purple lupine — set against New Hampshire’s rugged White Mountains — is like a massage for your optic nerves. At Harman’s Cheese & Country Store, scoop up crackers and a hunk of aged cheddar to stash in your pack before hiking to Bridal Veil Falls (via the family-friendly Coppermine Trail) or summiting Mt. Lafayette (Skookumchuck Trail is a toughie, but it’s well rated by hikers). 

6. Camden, Maine

Here’s a place so picture-perfect, it’s been used for filming scenes for HBO series and Hollywood films. Between big bowls of haddock chowder on the harbor, peep the handsome Queen Annes in the historic district or make your way up to the top of Mount Battie, where the view inspired Maine native Edna St. Vincent Millay to write one of her finest poems. And remember, it’s not a trip to Maine without some quality antiquing: Check this box at Antiques at 10 Mechanic.

7. Martha’s Vineyard, Massachusetts

Think of it this way: getting there is half the fun. Sure, the ferry to Martha’s Vineyard, sister island to Nantucket, can be a bit of a test for landlubbers, but once you disembark, you’ll find a  treasure trove of seaside villages, bike paths, and A+ lobster rolls. First stop: Waterside Market, where yummy breakfast sandwiches are served all day long (or opt for lobster salad on brioche straight out of the gate), then grab a cab or bike over to Oak Bluffs for beach time and frozen drinks at Nancy’s. Spend a day in pristine little Edgarton, with its indie shops (Edgartown Books is a real treat, as is the hidden cafe behind it), raw bars, and Greek Revival mansions.

8. Lakes Region, New Hampshire

Woods, rocky summits, hundreds of lakes and ponds: This ridiculously pretty area is based around Lake Winnipesaukee, the state’s largest lake. Set in the White Mountain foothills, the region seduces leaf-peepers, walkers, boaters, cyclists, and off-roaders in search of abundant outdoor activities.

It’d be a shame not to get on the water in the warmer months, so hop aboard one of M/S Mount Washington’s daily scenic cruises for a mimosa and postcard-worthy views of the surrounding mountains. Hikers have 28 miles of trails to explore at Castle in the Clouds and boundless views to enjoy at the top of Belknap Mountain, the highest peak in the area.

9. Woodstock, Vermont

There’s a ton of hype behind this small town. It’s been called the quintessential New England village and one of the most beautiful towns in the country, and both accolades are hard to argue with. At Billings Farm and Museum, say hi to the Jersey cows and draft horses, enjoy a maple sundae, and grab some smoked cheddar to go (it’ll make a tasty trail snack). Prue and Paul fans: Hop over to the neighboring town of Norwich to channel your inner Great British Baking Show contestant with a pie- and-tart-making class at King Arthur Baking Company.

10. Great Barrington, Massachusetts

Part of the Berkshires, Great Barrington looks straight out of a Louisa May Alcott novel. Everywhere you look are storybook old buildings now housing bakeries, upscale grocers, and farm-to-fork restaurants. (During the holidays, the town looks like the real-life version of a snow globe.) See what’s going on at Mahaiwe Performing Arts Center, a 1904 theater hosting everything from classic flicks to big-name bands.

11. Bar Harbor, Maine

Once upon a time (in the late 1800s), Bar Harbor was a summer oasis for the Vanderbilts, Rockefellers, Astors, and other VIP members of society looking to beat the heat. The appeal of this place takes no imagination; Bar Harbor is a quaint small town on Frenchman Bay and a gateway to Acadia National Park. Take a warm-up stroll along Bar Harbor’s shore path before diving into moody Acadia, where rocky shores and 150 miles of hiking trails are waiting. 

12. Portsmouth, New Hampshire

Drive about an hour north of Boston, and you’ll find the darling port town of Portsmouth. Kick off a walking tour at Market Square, hit the Portsmouth Harbor Trail, and dedicate a couple of hours to Strawbery Banke Museum — an outdoor museum with historic structures and costumed actors bringing three centuries of history to life. Reward yourself with the oyster happy hour and a cold local Smuttynose at Row 34 before moving on to dinner at Black Trumpet, a bistro and wine bar.

13. North Adams, Massachusetts

Art lovers have streamed into North Adams since 1999 when Mass MoCA opened in a previously abandoned 19th-century mill. Bed down at the art-filled Porches Inn, a series of Victorian homes that once housed textile workers. The draws of this small Berkshires city don’t end with Sol Lewitt’s wall drawings and Michael Oatman’s installation art, on view at Mass MoCA. Outdoor options include seeing the continent’s only natural white marble arch at Natural Bridge State Park and hiking Mount Greylock, the highest mountain in Massachusetts. 

14. Westerly, Rhode Island

Westerly may not have quite the vacay clout as Newport or the Vineyard, yet the coastal town balloons in the summer with beachgoers looking to hit Narragansett Bay and Misquamicut State Beach. Spend at least an afternoon in the ocean-view neighborhood of Watch Hill, visiting its 1850s lighthouse and setting out on its pristine Napatree beach hike.

15. Provincetown, Massachusetts

Journey to the farthest-flung tip of Cape Cod, and you’ll be rewarded with some of the area’s best stretches of sand, cool boutiques and art galleries, and an enchantingly funky and bohemian vibe. The LGBT hotspot has something for every mood, whether it’s drag karaoke, dance parties, and pub crawls that strike your fancy or catching the sunset on Herring Cove Beach.

16. Jackson and North Conway, New Hampshire

These sister towns in New Hampshire’s pretty Mount Washington Valley make a popular getaway, thanks to their waterfall hikes, scenic drives, small-town shopping (Schartner Farms has a drive-up, honor-system jam stand — how cute is that?), and big-box outlets. 

On the highway between the two towns is Sunrise Shack, an old-school drive-in-restaurant turned roadside staple for truly enormous breakfasts. After a summer swim at Echo Lake State Park or a challenging loop on Mount Chocorua, indulge in the biggest cone you’ve ever seen at Trails End Ice Cream.

17. Mystic, Connecticut

The Mystic Seaport Museum is a fascinating jumping-off point, with its million-plus artifacts depicting the town’s nautical life — you can even test out your sea legs on vessels like the Charles W. Morgan, the last wooden whaling ship that remains in the world today.

Drink up Long Island Sound and Fisher’s Island views at Bluff Point State Park and feast on some of the best seafood around at Oyster Club. Our perfect meal? Smoky Rhode Island clam chowder, dashi-buttery roasted oysters, and the homemade bucatini.

18. Montpelier, Vermont

Huddled in the foothills of the Green Mountains, the country’s smallest state capital brims with opportunities for nature activities, from hiking to the 4,000-foot peak of Camel’s Hump to whitewater rafting on the Winooski River. Of course, no trip to this neck of the woods is complete without a taste of what it does best. At Morse Farm and Bragg Farm maple sugar houses, you can sample the Vermont specialty in the form of maple cookies, kettle corn, or “creemee” (Vermontese for soft serve).

19. Kennebunkport, Maine

Like Mystic, Kennebunkport boomed as a shipbuilding hub during New England’s maritime heyday. The coastal town’s nautical vibe lives on, with glossy Italian-built yachts bobbing in the harbor and authentic schooners sailing toward the Atlantic. Kennebunkport swells in the summertime with New Englanders flocking to its beaches, but the town’s boutiques, cafes, and art galleries have year-round appeal.

20. Litchfield, Connecticut

Litchfield is a small town that more than carries its weight on the history, charm, and scenic beauty fronts. This picture-book spot in rural western Connecticut (birthplace of Revolutionary leader Ethan Allen and abolitionist Harriet Beecher Stowe) has an oak-shaded town green and hundreds of historic buildings. An area favorite for hiking and picnicking is the vast Topsmead State Forest, originally the summer estate (complete with a Cotswold-style cottage and formal gardens) of banking heiress Edith Morton Chase.