11 Best New England Towns For A Weekend Trip
After a long and hectic week of keeping your affairs in order, it is understandable to want a weekend to simply unwind and let go of all the troubles in the world. Fortunately, the United States’ New England region offers plenty of inviting options for lovely weekend retreats. If you seek beautiful fall foliage, head up to the Green Mountains for not just green, but also vibrant shades of red, orange, and gold. For something more beachy keen, try an escape to an idyllic island along the Atlantic coast. And when you crave a truly unique getaway, there is an extra special surprise in the hills of Connecticut.
Curious to see more? Well, you are in luck. These 11 best New England towns for a weekend trip will hopefully inspire your own ideal weekend escape.
Litchfield, Connecticut
Only about 100 miles north of New York City, you can escape to the town of Litchfield, a rural Connecticut village that is perfect for clearing your head and recharging your spirit. Head out to Kent Falls State Park to witness the journey of Falls Brook as its water drops down a series of cascades to the Housatonic River, and stick around for the amazing fall foliage if you are visiting during autumn. For more quality time in the great outdoors, there is also Mount Tom State Park, where you can do a short hike to the summit and take in the panoramic views extending from the Taconics and the Catskills all the way to Long Island Sound.
Back in town, take your pick of tasty local treasures to treat yourself with, from the casual pub-style fare at Bohemian Pizza and Tacos, to the refined New American dishes at the posh West Street Grill. Then, check into The Abner Hotel, the one-time Litchfield County Courthouse that has been reimagined and reinvented into a chic luxury boutique hotel with 20 guest rooms and the farm-to-table tavern-style Courtroom restaurant.
Mystic, Connecticut
With a name like Mystic, you can expect an enchanting Connecticut town and a magically pleasing feast for all senses. Go to Mystic Seaport Museum for quite the deep dive into the region’s nautical history, including the 1841 whaleship Charles W. Morgan and a re-created 19th-century maritime village. If you would rather walk yourself into nature, pop over to Denison Pequotsepos Nature Center and wander along its 10 miles of trails through the preserve’s woodlands, wetlands, and meadows where local wildlife like great horned owls, peregrine falcons, red-tailed hawks, and American kestrels call home.
When you are feeling more creative, try Mystic Museum of Art for a calendar full of interactive workshops and studio sessions, along with four galleries featuring works by American Impressionist and Tonalist artists. Once you have worked up an appetite, head next door to Oyster Club and enjoy authentic boat-to-table local seafood. Whenever you are ready to call it a day, retreat to The Whaler’s Inn for a uniquely scenic stay in the heart of Downtown Mystic.
Westerly, Rhode Island
Sitting at the southwestern corner of Rhode Island is Westerly, a lovely beach town with more to explore beyond the shore. Come for the beaches, such as those at Napatree Point Conservation Area, which serve as critical habitat for birds like piping plovers and ospreys, along with the nearby East Beach, offering great surfing and saltwater fishing. Stay to wander around Westerly’s downtown and find special local treasures, including the proudly independent Martin House Books and the tasty adult beverages at Tapped Apple Cidery and Winery.
For an exceptionally extravagant New England beach weekend, book a room or suite at Ocean House. Not only is this Rhode Island’s first and only official five-star resort, but it also sports a prime location at East Beach, the award-winning COAST restaurant, and comprehensive wellness offerings at Ocean & Harvest Spa.
Newport, Rhode Island
Just 39 miles south of Providence is Newport, perhaps Rhode Island’s premier coastal resort town with a grand Gilded Age pedigree. If you are keen to step into Newport’s rich past, make your way to The Breakers, the legendary waterfront estate built by the Vanderbilts in 1895, modeled after a Renaissance-era Italian palace. It is also worth stopping at Newport Art Museum to view their vast collection of early American and contemporary artworks, along with The Sailing Museum for a wonderfully interactive look into the history of sailing in Rhode Island and the United States.
When you feel like a nice day at the beach, Newport provides plenty of options, including the inviting shores at Sachuest Beach (or Second Beach) east of downtown. For even more beach time, make your way to Castle Hill Inn, a “luxuriously laid-back” Relais & Châteaux hotel with its own private beach and the highly regarded Aurelia at Castle Hill restaurant.
Provincetown, Massachusetts
Perched on the northern tip of Cape Cod is the fabulously cultured town of Provincetown. Start at the Pilgrim Monument and Provincetown Museum for the town’s iconic 252-foot all-granite tower commemorating the Mayflower Pilgrims’ first landing in North America in 1620, and stick around to learn more about the Wampanoag Indigenous people who called this land home long before the Pilgrims arrived. A short stroll away is Provincetown Art Association and Museum, featuring over 4,000 works by some 900 local artists and a calendar full of art workshops, classes, and community events.
Beyond the town, Provincetown also has some nice beaches. Try Herring Cove for calm waters on the bay side, and Race Point for a pristine Atlantic Ocean beach that is great for birdwatching. Whenever you are ready to settle down, park yourself at the Boatslip for beautifully refreshed waterfront accommodations. (The Boatslip also has a calendar full of live entertainment and LGBTQ-inclusive night parties.)
Great Barrington, Massachusetts
Near the southwestern corner of Massachusetts sits the stately village of Great Barrington, the perfect launchpad for all sorts of excursions and experiences across the Berkshires. If you need some space to stretch out, head out to Mount Washington State Forest for over 30 miles of hiking trails and additional opportunities for mountain biking, hunting, and cross-country skiing (in winter). Ski Butternut is another inviting option for winter sports with 22 trails across 100 skiable acres.
Whenever you are in town, there is a good chance that Mahaiwe Performing Arts Center will put on an amazing show, as they regularly feature live music acts, theatrical productions, comedy shows, and thought-provoking lectures. To refuel, stop at GB Eats for a cozy local diner with a tasty all-day breakfast menu (and plenty more lunch and dinner options). Then, check into the Wainwright Inn to enjoy this historically delightful country bed-and-breakfast that offers home-cooked breakfast every morning.
Woodstock, Vermont
While New England provides plenty of pretty options to spot fall foliage, there is nothing quite like the spectacular scenery in and around Woodstock. Prepare to be amazed upon arrival at Quechee State Park, thanks to the 165-foot-deep Quechee Gorge that is Vermont’s deepest and the vibrant display of fall colors all around (especially in early-to-mid October). For even more autumn colors and leafy views, hit the trails at Mount Tom Forest, which is part of Marsh-Billings-Rockefeller National Historical Park.
Right next to the national historical park, there is even more to see and do at Billings Farm & Museum, including touring their working Jersey dairy farm, meeting the other farm animals (including sheep, goats, and horses), and picking up delicious local cheeses and jams at the gift shop. If you crave more farm-fresh goodness, pop over to Woodstock Farmers’ Market, which is open six days a week (except Monday) and offers everything from fresh and organic produce to gourmet deli sandwiches and decadent pastries. And for the ultimate Woodstock experience, book a stay at Woodstock Inn & Resort to enjoy some legendary and luxurious local hospitality right in the heart of town.
Waitsfield, Vermont
Around 40 miles southeast of Burlington, discover the many fine treasures of the Mad River Valley and its gloriously sporty Vermont town of Waitsfield. To the southwest sit nearly 400,000 acres of protected public lands at Green Mountain National Forest, offering ample opportunities for autumn leaf peeping, mountain biking, camping, hunting, and fishing. Meanwhile, if you come during the winter season, pull out your skis and snowboards, and prepare for epic rides downhill. More specifically, Sugarbush offers up to 2,600 feet of vertical drop across 484 skiable acres, while Mad River Glen provides up to 2,037 feet of vertical drop across 115 skiable acres.
Whatever you end up doing in the mountains, Waitsfield makes it easy to relax and unwind in town. For mature flavors and classic refreshment, step into Lawson’s Finest Liquids taproom to taste their award-winning craft beers. Then, check into the Featherbed Inn & Nordic Spa for a supremely serene environment anchored by a historic (1806) farmhouse and featuring a full Nordic spa with a traditional sauna and a year-round outdoor hot tub.
Carroll, New Hampshire
Perched high in the White Mountains of northern New Hampshire is Carroll, a rugged mountain town with a surprisingly worldly backstory. In 1944, some 730 delegates from 44 nations gathered here to establish what would become the post-World War II Bretton Woods monetary and financial system. To see “the room where it happened,” head up to the Omni Mount Washington Resort & Spa. Not only does it have a long history of welcoming dignitaries to New Hampshire, but it’s also connected to Bretton Woods Ski Area, the state’s largest ski resort with 464 acres of skiable terrain and ample family-friendly trails.
Beyond the Bretton Woods resort area, Carroll really excels in great outdoor experiences. For a special journey to New England’s highest summit, take the Mount Washington Cog Railway, which has been making the journey through three climate zones to the 6,288-foot peak since 1869. Once you make it to the summit, take in the incredible views at the top, and stop at Mount Washington Observatory to tour this working weather station. And if you are really up for a challenge, Mount Washington also has a few challenging yet very scenic hiking trails.
Carrabassett Valley, Maine
Carrabassett Valley may only be around 76 miles north of Augusta, yet this storied ski town looks and feels far removed from the troubles of the world. This especially rings true at Sugarloaf Ski Resort, Maine’s largest ski area at 1,360 acres, and its tallest, which offers up to 2,820 feet in vertical drop. Or, if you make it to town before ski season begins, take a hike in Shiloh Pond Community Forest to take in the fall foliage views, and try fly fishing at the pond. Also in the area is Bigelow Preserve, a 10,540-acre preserve of Appalachian Mountain wilderness where you can connect to the larger Appalachian Trail that extends from Mount Katahdin all the way down to Georgia.
After working up an appetite in the mountains, head down into town and stop at The Rack for authentic maple wood-smoked, Maine-style barbecue. Then, check into the Sugarloaf Mountain Hotel for a convenient and comfortable lodge within walking distance of the ski area.
Lubec, Maine
At the very easternmost corner of the continental United States is Lubec, a town so special that it has an international park that spans across the border. Yes, really, you can hop across the Franklin Delano Roosevelt Bridge (and the US-Canada border crossing) to Roosevelt Campobello International Park to tour the Roosevelt family’s beloved summer beach house. While on Campobello Island, you can also walk around the natural area and discover special treasures along the Bay of Fundy coast, like Raccoon Beach on international park grounds, and Herring Cove Provincial Park, a little farther north.
Back on the US side of the bridge, there is plenty more to explore around Lubec. Head down to Quoddy Head State Park to find the iconic red-and-white-striped West Quoddy Head Lighthouse that has been illuminating the coast since 1808. Farther south is Boot Head, a beautiful waterfront nature preserve with cobble beaches, coastal bogs, and promontories sporting incredible panoramic views. And for more quality time by the sea, check into the West Quoddy Station near the state park to “stay where the sun rises first.”
Come for the Weekend, and Stay for Beautiful Lifelong Memories
When you can use a long weekend and a quick getaway, New England has plenty of appealing and satisfying options. Make your way to Mystic for a gnarly nautical experience, and try Newport for a historically elegant beach retreat. Provincetown is another picture-perfect beach town that abounds in vibrant art and culture, while Woodstock shines in farm-fresh flavor and hospitality. Ascend to the top of New England in Carroll, and experience the uniquely Downeast sights and sounds of Lubec. With so much to experience across New England, it is totally understandable if you want more than just one weekend.
