New England is a place that deserves a lifetime of weekend vacations because it has picture-perfect countrysides, cliff-lined coasts under the watchful gaze of centuries-old lighthouses, and innumerable small villages to discover. Here are 20 unique getaways in New England, perfect for a romantic trip or a last-minute jaunt out of town.
best weekend getaways in new england
North Adams, Massachusetts
Visitors interested in art have flocked to North Adams following the 1999 opening of Mass MoCA in a derelict mill from the nineteenth century. The Porches Inn is a collection of Victorian mansions that formerly housed textile workers; it is loaded with art, and the Hotel Downstreet is another option. Michael Oatman’s installation art and Sol Lewitt’s wall drawings at Mass MoCA aren’t the only draws of this little Berkshires city. At Natural Bridge State Park, you may witness the continent’s only natural white marble bridge. Another outdoor activity is hiking up Mount Greylock, Massachusetts’s highest peak.
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Martha’s Vineyard, Massachusetts
Consider this: half the enjoyment is in making it there. Getting to Martha’s Vineyard, Nantucket’s sister island could be a challenge for those who live on land, but once you get off the boat, you’ll discover a paradise of beach towns, bike lanes, and delicious lobster rolls. Get a cab or ride your bike to Oak Bluffs for beach time and frozen drinks at Nancy’s. Waterside Market has delicious breakfast sandwiches all day, or you may choose lobster salad on brioche right out of the gate. Edgartown Books and the hidden cafe behind it are must-visit indie shops; raw bars, Greek Revival homes, and quaint boutique hotels like Faraway Martha’s Vineyard are great places to spend a day in picture-perfect Edgartown.
Nantucket, Massachusetts
There is tremendous reverence for this 50-square-mile patch off the coast of Massachusetts, particularly during summer vacations. But set aside the chain eateries and cars that mar your picture-perfect beach backdrop. Alternatively, take the island shuttle or cycle to see the historic lighthouses (Brant Point is still in operation and dates back to 1746), the opulent mansions of the whaling captains, and the relaxed beaches. Refuel with a freshly cooked bay scallop or lobster roll every few hours, and then spend the night at one of the waterfront resorts, such as White Elephant Nantucket.
Great Barrington, Massachusetts
In the Berkshires, Great Barrington appears as though it were plucked from a Louisa May Alcott novel. Old, picturesque buildings repurposed as bakeries, gourmet markets, and farm-to-table eateries dot the landscape. (The village appears like a snow globe during Christmastime.) The Mahaiwe Performing Arts Center has entertained audiences with everything from historical films to major bands since its opening in 1905.
Mad River Valley, Vermont
Located underneath the well-known ski resorts of Sugarbush and Mad River Glen, Vermont’s Mad River Valley is an incredibly picturesque location. And that’s on top of an unexpectedly glamorous past (Vogue once dubbed Sugarbush “Mascara Mountain” because so many stylish model types frequented its slopes). In addition to exciting off-slope activities like mountain biking, farm stand shopping, and summer concerts, skiing is still outstanding in this area.
Woodstock, Vermont
Woodstock is a picture-perfect New England village with historic covered bridges, charming cafes, and Victorian mansions. Stop by Billings Farm and Museum to greet the draft horses and Jersey cows, have a maple sundae, and pick up some smoked cheddar for a delicious trail snack. Prue and Paul admirers: Taking a pie and tart baking lesson at King Arthur Baking Company in the nearby town of Norwich is a great way to unleash your inner Great British Baking Show contestant.
Newport, Rhode Island
Viewers of HBO’s Gilded Age should visit Newport, the preferred summer vacation destination for the affluent of the late 19th century. Admire Newport’s opulent houses on one side and the Atlantic Ocean slamming against rocks on the other by strolling along the Cliff Walk. After working up an appetite on the 3.5-mile trail, you’ll be ready to eat like a Vanderbilt. Try the (BYOB!) breakfast at Cru Cafe or treat yourself to a lobster mac ‘n’ cheese at the iconic Brick Alley Pub.
Sugar Hill, New Hampshire
Sugar Hill offers city dwellers a leisurely pace, breathtaking scenery, and many reasons to enjoy it. Seeing lupine fields, which are a deep purple color, or vivid fall foliage juxtaposed against the untamed White Mountains of New Hampshire can soothe your ocular nerves. Grab some crackers and a chunk of aged cheddar cheese at Harman’s Cheese & Country Store to take in your pack before heading up Mount Lafayette (the challenging but hiker-rated Skookumchuck Trail leads to Bridal Veil Falls) or trekking to Bridal Veil Falls via the family-friendly Coppermine Trail.
Litchfield, Connecticut
Despite its diminutive size, Litchfield packs a significant punch when it comes to history, charisma, and breathtaking natural beauty. Hundreds of historic houses line the picturesque town green in rural western Connecticut, the birthplace of abolitionist Harriet Beecher Stowe and Revolutionary War leader Ethan Allen. Formerly the vacation home of banking heiress Edith Morton Chase, the expansive Topsmead State Forest is a popular spot for picnics and hikes. The estate included a Cotswold-style villa and formal gardens.
Lakes Region, New Hampshire
Surrounding New Hampshire’s largest lake, Lake Winnipesaukee is an incredibly picturesque region characterized by woods, high summits, and hundreds of lakes and ponds. Outdoor enthusiasts such as hikers, bicyclists, boaters, and off-road enthusiasts flock to this region in the foothills of the White Mountains.
Sailing on the lake during the warmer months is an absolute must. Take advantage of the M/S Mount Washington’s daily scenic cruises, where you may sip a mimosa while taking in picture-perfect vistas of the neighboring mountains. The highest point in the region, Belknap Mountain, offers hikers limitless views and 28 miles of paths to explore at Castle in the Clouds.
Block Island, Rhode Island
Block Island appears in England with its majestic Victorian-style hotel, plains covered in native vegetation, and towering bluffs. The saltbox buildings with cedar shingles remind us that we are in New England, not some wind-swept United Kingdom region. This classic coastal retreat, 13 miles off the coast of Rhode Island, is as much about driving along rural lanes and seeing expansive heathland as it is about going to the beach.
Bar Harbor, Maine
Bar Harbor was a summer retreat for affluent families like the Vanderbilts, Rockefellers, and Astors when it was hot outside. That was in the late 1800s. The picturesque little hamlet of Bar Harbor, located on Frenchman Bay and serving as the park’s entry point, is an attraction that needs no introduction. Prepare for the gloomy Acadia National Park by taking a leisurely walk down the shore path in Bar Harbor. The unique getaways in new england, park is home to 150 miles of hiking trails and rocky shores.
Camden, Maine
Camden is a well-liked setting for TV series and Hollywood movies; frequently referred to as one of the most picturesque small towns in the United States. See the elegant Queen Anne-style homes in the historic area or ascend Mount Battie, where the vista prompted Maine native Edna St. Vincent Millay to pen one of her best poems after savoring a hearty bowl of haddock chowder on the waterfront. And always remember that a trip to Maine would only be complete with some excellent antiquing: browse the unique getaways in new england, treasures at Antiques at 10 Mechanic.
Kennebunkport, Maine
During the maritime era of New England, both Mystic and Kennebunkport were thriving shipbuilding centers. Authentic schooners sail into the Atlantic, while shiny boats built in Italy bob in the harbor, preserving the nautical spirit of the seaside town. While the summer months see a dramatic increase in visitors to Kennebunkport’s beaches from around New England, the town’s shops, restaurants, and galleries remain popular all year round.
Portsmouth, New Hampshire
Portsmouth is a charming little town located around one hour north of Boston. Market Square is a great place to start a walking tour; from there, take the Portsmouth Harbor Trail and spend a couple of hours at the outdoor museum Strawbery Banke, where you can see structures from three centuries of history brought to life by costumed players. Before heading to Black Trumpet, a cafe and wine bar, treat yourself to an oyster happy hour and a frosty local Smuttynose at Row 34 for supper.
Westerly, Rhode Island
Though it has the vacation gravitas of Newport or the Vineyard, the seaside hamlet of Westerly experiences a summertime explosion of visitors eager to visit Narragansett Bay and Misquamicut State Beach. The ocean-view community of Watch Hill is the perfect place for a classic New England weekend retreat. While there, take in the views, explore the unique getaways in new england, 1850s lighthouse, and stroll down the beautiful beach at Napatree Point Conservation Area.
Provincetown, Massachusetts
If you make it to the tip of Cape Cod, you’ll find some of the most excellent beaches in the region, as well as hip shops, galleries, and a charmingly bohemian atmosphere. Whether you’re in the mood for drag karaoke, dance parties, bar crawls, or want to watch the sunset on Herring Cove Beach, this LGBTQ-friendly community has it all.
Jackson and North Conway, New Hampshire
Hikes to waterfalls, picturesque roads, and a mix of small-town shopping (Schartner Farms, for example, has a drive-up, honor-system jam stand—how adorable!) and big-box retailers make these sister towns in New Hampshire’s picturesque Mount Washington Valley a favorite retreat.
An iconic roadside attraction known for its large breakfasts, Sunrise Shack is an old-school drive-in diner on the unique getaways in new england, highway between the two cities. Indulge in the giant cone you’ve ever seen at Trails End Ice Cream after a summer swim at Echo Lake State Park or a problematic walk on Mount Chocorua.
Mystic, Connecticut
Those interested in New England history and seeking a fun weekend destination would adore this historic shipbuilding center. You can get your sea legs on ships like Charles W. Morgan, the unique getaways in new england, last wooden whaling ship in the world today, and explore the town’s maritime history at the Mystic Seaport Museum, which houses over a million objects.
Bluff Point State Park offers breathtaking views of Fisher’s Island and Long Island Sound, while Oyster Club serves up some of the area’s finest seafood. Our ideal dinner? Oysters cooked in dashi butter, handmade bucatini, and smoky Rhode Island clam chowder.
Montpelier, Vermont
Located in the Green Mountain foothills, the least populous state capital in the US offers a wealth of outdoor recreation choices, such as whitewater rafting on the Winooski River and trekking to the top of Camel’s Hump, which is 4,050 feet. A visit to this area would only be complete with sampling its specialties. Maple sugar homes at Morse Farm and Bragg Farm allow visitors to taste this Vermont delicacy in various forms, including maple cookies, kettle corn, and “creemee” (soft serve in Vermont).
