7 Stress-Free Massachusetts Towns For A Weekend Retreat
The hardest part about taking a weekend retreat in Massachusetts? Deciding between the mountains and the ocean. If you want to find your inner zen in the Berkshires, hidden communities like Lenox, Great Barrington, and Stockbridge deliver those fresh mountain retreat vibes. If your soul needs salty sea breezes and minimal crowds, Nantucket and Newburyport maintain their small-town identities without crowded beaches and commercial high-rises. So, when you’re ready to leave your worries behind, let these lovely retreats tend to your weary soul.
Lenox
The hidden gem of Lenox is on the western edge of Massachusetts, near the New York border. Located in the Berkshires, it’s a blend of outdoor recreation and a charming downtown district with so much to see and do. One of the must-see attractions in Lenox is The Mount, the former home of the famous American author Edith Wharton. Even if you aren’t familiar with her works, touring her home is simply stunning. The gardens bloom in vibrant colors in the spring and summer, and the mansion feels like stepping back in time.
If you long for a spa day, Lenox has you covered! The Miraval Berkshires Resort and Spa are sure to melt away your stress in an afternoon. Think lounging on deck chairs poolside with a cucumber water in hand and a massage scheduled later that afternoon. It’s also one of the best places to stay in Lenox, with lavish accommodations with views of the Berkshires out your window. And after a day unwinding at the spa, you can head out for a healing hike at the Pleasant Valley Wildlife Sanctuary or Kennedy Park.
Stockbridge
As a year-round resort destination in the Berkshires, Stockbridge is a lovely retreat to slow down for a long weekend. It is so beautiful that it inspired many of Norman Rockwell’s paintings. So, if exploring Stockbridge feels like stepping inside a painting, you’re not too far off the mark. The Norman Rockwell Museum is just outside of town, showcasing his works and his former studio. While the inside of the museum is amazing, in true Norman Rockwell fashion, the hilltop location is just as breathtaking.
While you won’t find too many hotels in Stockbridge, there are plenty of cozy Inns and B&Bs to choose from. The most famous of the bunch is the Red Lion Inn, which has hosted US presidents and famous poets since its opening as a tavern in 1773. It’s like a cozy English garden tucked away in the Berkshires. The Inn is centrally located in Stockbridge and within walking distance to historic landmarks like the Mission House and scenic nature, like Laurel Hill.
Newburyport
If there’s one place that’s sure to offer a stress-free weekend, it’s the ocean. That’s not a tight-lipped secret. Many coastal retreats have similarly-minded tourists, making crowds ebb away at your inner zen. Newburyport, however, hardly sees the summer crowds. It’s where you can go for a stroll down the Harborwalk Rail Trail and watch colorful sailboats dock at the port, or sit on a bench at Waterfront Park. The best way to feel like a local in Newburyport is by staying at one of their quaint inns, like the Compass Rose Inn, a modern inn constructed to reflect Newburyport’s federal style architecture.
When you’re ready for even more seclusion in Newburyport, Plum Island is less than a 20-minute drive away. Home of the Parker River National Wildlife Refuge, it’s a naturalist's paradise of undisturbed habitats, perfect for birdwatching, hiking, swimming, or taking in the sweet, salty sea air. Newburyport delivers all the tranquil vibes of a beachy resort, minus the crowds, noise, and traffic.
Ashfield
Traveling far from the Atlantic Ocean to western Massachusetts, Ashfield is the type of place that feels like home. Central Ashfield is quite small, with a collection of locally-owned eateries like Laughing Crow Café or Ashfield Lake House nestled along the tranquil banks of Ashfield Lake. A community like Ashfield doesn’t have a lot of commercial hotels in town, but they have delightful inns, like Norton Hill B&B! Expect cozy accommodations in a stunning inn built in 1795.
The best thing about staying in Ashfield is the amazing trails outside the city limits. Bear Swamp Reservation is less than a 10-minute drive from the Norton Hill B&B and offers some of the most amazing scenery in the area. It’s a quiet, remote 312-acre preserve that blooms with wildflowers in the spring and summer, with the Green Mountains in the distance. It’s just one of the many hiking opportunities surrounding the picturesque community of Ashfield.
Nantucket
If you’re after peace and quiet, there’s no better place in Massachusetts than Nantucket. To say it’s an isolated community is a bit of an understatement. It’s an entire Island off the coast of Cape Cod that’s only accessible by ferry. Most residents and visitors of Nantucket walk or bike everywhere, so the sounds of the waves won’t be spoiled by a loud car radio or a noisy muffler! The beaches in Nantucket are unspoiled by commercial hotels or high rises. Beaches like Sconset Beach on the east end or Madaket Beach on the western tip offer dreamy oceanside vistas where you can allow your worries to wash out with the tide.
Downtown Nantucket is almost as dreamy as its windswept beaches. With cobblestone streets, minimal traffic, and salty sea air, it is easy to lose track of time. There are unique historical landmarks, like Jethro Coffin House (built in 1686 and the oldest house in Nantucket), or the Maria Mitchell Hinchman House Natural Science Museum. If you want to stay close to the beach and local coffee shops, the Brass Lantern Inn is one of the best places to stay on the island!
Great Barrington
The small Berkshire community of Great Barrington is one of those unique places where the vibes are laid back, but there’s always something unique to discover. It’s close to some of the best trails in the Berkshires but has yet to fall into touristy-hub territory. Local cafes like The Prairie Whale serve up classic American food in a modern setting, and the croissants from Patisserie Lenox are a must-try! And of all of the cozy inns of Great Barrington, the Granville House feels like a rustic inn amid the lush greenery of the Berkshires.
Central Great Barrington has all the modern amenities of home to prepare you for the wonderful hiking opportunities surrounding the city! If you long to relax at the lakeside, Lake Mansfield Recreation Area is one of your best options! It's the perfect place to spend a long weekend with clear waters, lush greenery, and shaded hiking trails. When you want a better view, the Monument Mountain Reservation has more challenging hikes, but you can’t beat that panoramic view from the top!
Deerfield
Nothing has changed in Deerfield since its founding in 1677 in all the best ways. The entire town feels like a well-preserved time capsule from the 18th century, with its lush tree-lined streets and white church steeples piercing the sky. It’s where you tour pristine relics of the past, like the Frary House, or Historic Deerfield, where you can tour a cluster of 18th-century homes, offering tours and craft demonstrations. You won’t find commercial hotels in this hidden gem, but rather friendly inns and B&Bs that will make you feel at home, like the Deerfield Inn.
While it’s easy to get lost in the old world charm of central Deerfield, there’s a wild wilderness to explore just outside its city limits. One of the more popular hiking destinations in the area is the Mount Sugarloaf State Reservation. The park sits on almost 600 acres in the Connecticut River Valley and has 4 accessible trails that lead to amazing views of the Berkshire Hills and Pioneer Valley.
Overwrought itineraries have no place in these sleepy towns. They are the kind of place where you see where the day takes you. Maybe you stroll down Main Street in the morning looking for that quiet coffee shop, watch the sunrise over the ocean (or the mountains), or explore a quaint museum or two. No matter what type of weekend soothes your soul, you’re bound to find it in Massachusetts. The only thing these retreats lack is traffic, crowds, and noise, making them the perfect getaway.
