New England’s coastline is a beloved vacation destination for a reason, with its string of charming seaside towns, no-frills lobster shacks, and wide-open beaches from Maine down to Connecticut—but there are plenty of worthwhile destinations further inland, too. Below we’ve highlighted four of our favorite Inspirato destinations tucked amid the rolling hills and meadows of the New England countryside.
In central Connecticut, the town of Washington offers a quintessential New England pastoral retreat. Made up of five quaint villages, Washington has a storied past, dating back to the 1700s. The rural town is now known for its vineyards, charming town festivals, and celebrated colonial architecture. It’s thought to be the inspiration for Stars Hollow, the fictional setting of “Gilmore Girls.”
Nestled in northwestern Vermont, Stowe is a quaint storybook town that offers something for every season: maple syrup tasting and colorful fall foliage each autumn, legendary skiing in the winter, and gondola rides to the top of Mt. Mansfield (the state’s highest peak) where hiking trails await in the warmer months. Pop into beloved mom-and-pop stores like the Vermont Flannel Company, sample seasonal flavors at the Ben & Jerry factory, and sip award-winning spirits at Smugglers’ Notch Distillery.
The Berkshires, Massachusetts
Discover a wealth of natural beauty and quaint resort towns in the Berkshires of western Massachusetts. Visitors often enjoy popping into the many galleries, theaters, and museums that populate the mountain towns. Williamstown, home to Williams College, is an epicenter of cultural activity, including the venerable Clark Art Institute as well as the Williams College Museum of Art. Fuel up at independent restaurants and cozy, historic pubs.
Tucked in the Green Mountain National Forest of southern Vermont, the town of Stratton is an outdoor lovers’ paradise. It’s credited as the birthplace of snowboarding, and home to Stratton Mountain School, a college preparatory high school with a focus on winter sports—the school counts numerous Olympians, including gold medalist Lindsey Jacobellis, among its alumni. Stratton Mountain Resort is an all-season hub, with skiing and snowboarding in the winter and hiking and mountain biking in the warmer months.