12 Serene New England Towns For A Weekend Retreat

Perched between the United States’ economic powerhouse of New York, the distinctly French Canadian province of Quebec, and the maritime traditions of Atlantic Canada, the U.S. region of New England occupies a special corner of the North American continent. From the laid-back woodlands of Massachusetts’ Berkshires to the spectacular beaches of Rhode Island, New England has plenty of places to kick back, relax, and enjoy a long weekend. And if you seek a more adventurous weekend getaway, there’s hardly ever a bad time to retreat to the Green Mountains of Vermont or to the rugged coast of Maine.

Whether you seek some pristine mountain wilderness to hike or a posh wellness-centered resort for luxurious pampering (or maybe both), New England has ample options for the ideal weekend holiday. Here are 12 of our picks for serene New England towns for a weekend retreat.

Washington, Connecticut

Perched in the Litchfield Hills of northwestern Connecticut, about 93 miles northeast of New York City, the village of Washington is rich in fascinating history, lovely scenery, and contemporary luxury. For some cool history lessons, visit the Institute for American Indian Studies, which preserves and shares some 12,000 years’ worth of artifacts and stories chronicling the journey of North America’s indigenous communities. There’s also the Gunn Memorial Library & Museum, that’s housed in an original 1781 house, and The Silo at Hunt Hill Farm, that’s home to Connecticut’s oldest (and now UNESCO-recognized) institute of culinary arts.

When you can use a simple escape into nature, head up to Mount Tom State Park for a network of leafy hiking trails and Mount Tom Pond for swimming and boating. Also nearby, you can go to Lake Waramaug State Park for perhaps the Nutmeg State’s prettiest fishing lake. For the ultimate in Washingtonian hospitality, check into The Mayflower Inn & Spa for the region’s premier boutique resort, one that seamlessly combines classic New England country style with contemporary creature comforts.

Mystic, Connecticut

Perhaps best known for inspiring the 1988 rom-com Mystic Pizza that launched the careers of actors like Julia Roberts and Matt Damon, the real-life town of Mystic might be even more heavenly than the fictionalized version. Yes, there’s an actual Mystic Pizza where you can get in line to try their world-famous pies. In addition, Mystic has restaurants like La Plage Mystic, S&P Oyster, and The Irons where you can feast on locally sourced seafood and indulge in contemporary takes on classic New England cuisine.

Beyond the restaurants, there’s even more to see and do around Mystic. At Mystic Seaport Museum, find the Charles W. Morgan, the last wooden whaleship in the world, spot other historic boats like the Joseph Conrad ship and the Sabino steamboat, and tour their re-creation of a 19th-century fishing village. At the nearby Denison Pequotsepos Nature Center, hike their network of wetland and woodland trails and spot birds like Peregrine Falcon, Red Tailed hawks, and American Kestrels. At the Delamar Mystic, check into a fun and funky hotel where old-school New England maritime tradition meets cutting-edge new luxury by the Mystic River.

Block Island, Rhode Island

Accessible by ferry from Narragansett and Newport, Block Island looks and feels a world away from the hustle and bustle of the mainland. So, what is there to do? For starters, explore the island’s many beautiful beaches. Admire the historic North Light House and the coastal scenery at Cow Cove, jump into the perfect snorkeling water at Surf Beach, go surfing at Black Rock, and look for sea glass at West Beach. For even more stunning natural scenery, do some bird watching at Clay Head Preserve and wander the wilderness trails at Block Island National Wildlife Refuge.

To complete the ultimate weekend at Block Island, book a stay at The 1661 Inn, a family-owned and operated resort that provides all the comforts of life in a uniquely charming setting near some of the island’s best beaches.

Little Compton, Rhode Island

Situated on Rhode Island’s Farm Coast, Little Compton is a special place where rolling green fields meet the Atlantic Ocean. Around town, you can discover unique treasures like Simmons Mill, a nature preserve with a tranquil pond and a network of pleasant walking trails. Just farther north, Weetamoo Woods & Pardon Gray Preserve spans some 750 acres of pristine wildlife habitat, and it even has trails suitable for horseback riding.

Of course, no visit to Little Compton feels complete without some quality time at the beach. Head to South Shore Beach for a compact stretch of sand with clean water for swimming and wading, and enjoy the views over at Town Landing. For even more seaside experiences, do a stay at The Stone House Inn, a historic 1854 manor that’s now a glorious boutique hotel with private beach access.

Chatham, Massachusetts

Nestled on the “elbow” of the Cape Cod Peninsula, about 88 miles southeast of Boston, Chatham provides a less hectic and more relaxing side of the Cape. This town has plenty of long and storied history, and you can peruse some of it at the Mayo House, a home first built in 1820 that’s furnished with traditional period pieces and open for tours every summer. There’s also the Chatham Railroad Museum, housed in a vintage 1887 train station and a real haven for train lovers. At Monomoy National Wildlife Refuge, you can spot the Monomoy Point Lighthouse that’s stood all at the shore since 1823 and wander the nature trails to find the stunning beaches on Morris Island.

Speaking of beaches, Chatham has even more amazing beaches worth visiting, including the serenely calm water at Oyster Pond, and the lovely sand dunes at Hardings Beach. After a long day of exploring the coast, settle down without settling for less at Chatham Bars Inn, the town’s only Forbes five-star luxury hotel with the most acclaimed full-service spa that offers all the treatments you need for the most relaxing weekend.

Provincetown, Massachusetts

Over the years, the village of Provincetown at the tip of Cape Cod has developed a reputation as one of the United States’ premier LGBTQ+ summer destinations. Indeed, bars and clubs like the Crown & Anchor, Bubala’s, and The Underground are fun spots to enjoy a boisterous night out. Yet, throughout the day, there’s even more to experience in P-town. For a nice time at the beach, try a swim at Herring Cove Beach, and do a hike to the secluded shores of Long Point Beach that’s adorned with an 1875 vintage lighthouse (that was equipped with solar power just over a century later).

To better understand Provincetown’s fascinating backstory and rich culture, head to the Provincetown Museum to behold the 252-foot-tall all-granite Pilgrim Monument and learn about this town’s evolution from Wampanoag indigenous settlement to the site of the English Pilgrims’ arrival to the New World, and its subsequent journey to becoming a safe haven for LGBTQ+ Americans. Also check out the Provincetown Art Association and Museum to discover works by local artists and attend its regular program of artistic workshops and lectures. For the best finishing touch to your P-town getaway, book a stay at The Brass Key for a refined yet fun boutique hotel at the center of the action.

Lenox, Massachusetts

Tucked away in the Berkshires of Western Massachusetts, the town of Lenox is the heart of the region’s famously creative spirit. During the summer season, Tanglewood is the Berkshires home base of the Boston Symphony Orchestra, and you will find a variety of classical, jazz, avant garde new music, and musical theater productions happening all season long. To catch more of Lenox’s artistic heritage, visit The Mount and tour the country estate of the Pulitzer Prize-winning author Edith Wharton, and stop at the Frelinghuysen Morris House & Studio to get to know the cool couple who pioneered abstract modern art in the 1930s and 40s. For some classic Americana, it’s a short drive out to the Norman Rockwell Museum and the world’s largest collection of his original art.

When you’re more in the mood to experience the handiwork of Mother Nature, go to the Pleasant Valley Wildlife Sanctuary to hit the preserve’s network of trails spread across 1,000 acres of forest, meadows, wetlands, and the slopes of Lenox Mountains. And when you can use a wholesome weekend-long healing journey, Lenox has the Canyon Ranch and Miraval resorts with luxurious accommodations, full-service spas, and calendars full of wonderful wellness activities.

Middlebury, Vermont

Middlebury may be a college town, but this Vermont town goes above and beyond the stereotypical “college town” offerings. For one, Middlebury offers ample opportunities for exciting outdoor recreation year-round, its extensive hiking trail network that includes the local Trail Around Middlebury and connections to The Long Trail that traverses Vermont’s highest mountain peaks, to Middlebury College’s Snowbowl and Rikert Outdoor Center for wintertime skiing. Even if you prefer aquatic activities, Middlebury is a short drive away from Branbury State Park with its sandy beach, designated swimming area, and opportunities for kayaking, boating, and fishing.

Back in town, Middlebury offers plenty more to see and do, including an eclectic array of ancient, classical, and contemporary art at the Middlebury College Museum of Art and the charmingly historic Pulp Mill Covered Bridge. Finish the day with a delectable dinner and a restful night at the lovely Swift House Inn.

Woodstock, Vermont

Nestled in Vermont’s iconic Green Mountains, the village of Woodstock oozes timeless New England-style mountain town scenery and hospitality. For some epic views, hike the trails of Marsh-Billings-Rockefeller National Historical Park to reach the top of Mt. Tom and The Pogue mountaintop pond. Right next to the park, Billings Farm provides truly interactive learning experiences with farm animals (including cows, sheep, horses, and chickens), kids’ discovery days, crafty workshops for adults, and a gift shop stocked with some of the region’s tastiest artisan cheeses.

If you fancy a different kind of entertainment in Woodstock, check the event calendar for Woodstock Town Hall Theatre, which hosts a fun variety of live music concerts, theatrical productions, and movie screenings. When you’re more in the mood for rest and relaxation, check into the Woodstock Inn & Resort for an elegant yet comfortable take on New England craftsmanship and creativity. (The hotel also has great restaurants on site!)

Carroll, New Hampshire

Perched high in the White Mountains of northern New Hampshire, Carroll makes the ideal base camp for all sorts of thrilling adventures. A short drive from town is Mount Washington, the tallest peak in New England at 6,288 feet above sea level. What makes Mount Washington even more special is the fact that you can ride the historic 146-year-old Mount Washington Cog Railway all the way to the summit and tour the working research station (by reserving in advance) at Mount Washington Observatory.

Just beyond Mount Washington, there’s even more to explore around Carroll, including the trails leading to gorgeous mountain vistas and waterfalls at Crawford Notch State Park, and fly fishing at the Ammonoosuc River at Twin Mountain. For even more activities (as well as accommodations) year-round, head over to the Omni Mount Washington Resort in nearby Bretton Woods for elegant rooms and suites, a full-service spa with heated pools, the Mount Washington Golf Club, and the Bretton Woods Ski Area.

Kennebunkport, Maine

Located near the southern tip of Maine, Kennebunkport is a stately seaside village that became world-famous when then-U.S. President George H.W. Bush made the family beach house into his Summer White House. Though the Bush family compound is not open to the public, the nearby Colony Beach is, and it’s a pleasantly compact beach to touch the water, try some saltwater fishing, and watch the boats as they sail by. For a longer beach with perfect conditions for swimming and beachcombing, head north to Goose Rocks Beach. For the area’s best surfing beach, Gooch’s Beach is near the harbor and the Kennebunkport Historic District.

Meanwhile, in the Historic District, you can tour historic landmarks like the grand White Columns estate that’s stood in town since 1853 and the vintage 1900 Town House School. Also in town, feel free to explore the present-day arts scene at galleries like Thompson & Company and From Sea to You. After a long day traipsing around town, settle down at the oasis of Maine-style casual luxury that is the White Barn Inn.

Camden, Maine

The town of Camden prides itself on its special place “between the mountains and the sea,” and this unique location makes Camden the perfect place to embark on epic excursions. Directly north of town, Camden Hills State Park has a network of hiking trails ascending to the peaks of Mt. Battie and Mt. Megunticook, and it’s great for cross-country skiing and snowshoeing during winter. Near the state park, Barrett’s Cove is the area’s largest freshwater swimming beach at Megunticook Lake.

For saltwater fun and games, Laite Memorial Beach is a nice spot to watch the boats sailing in and out of the harbor, while Aldermere Farm is an actual working cattle farm offering tours of the agricultural areas and walking trails along this rugged stretch of the Atlantic coast. Back in town, treat yourself to a sumptuous stay at the Camden Harbour Inn, an award-winning boutique hotel offering opulent yet cozy accommodations with beautiful harbor and village views.

New England Is Perfectly Serene For All Kinds Of Weekend Retreats

When you’re looking for the ideal place for a long weekend escape, try one of these serene New England towns to make the most of it. At Mystic, dive deep into the region’s rich maritime heritage. At Provincetown and Lenox, discover New England’s fiercely independent artistic spirit. And at Woodstock and Carroll, take in the clean mountain air and enjoy the scenery on the wilderness trails. Whether you aim to ascend to the highest peaks, take a dip at the beach, or simply relax and de-stress, these New England towns will help you find your ideal sense of serenity.