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Beautiful New England Towns Perfect for a Summer Retreat

Pack your bags and hit the beach at these picturesque New England towns.

Photography by Michael Denning


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For most of us, the mention of New England in the summer leads to visions of quaint towns, lighthouses, beachside clambakes, lobster rolls, and chowder. Sandy shores, lakeside cottages, and chilly evenings around a fire pit also fit the picture very nicely. There’s a good reason our imagination creates those images. They describe New England summers perfectly.

We’ve gathered a few destinations from the New England states, huddled in America’s northeast corner along the Atlantic and blessed with inland mountains. Most fulfill the dream of historic lighthouses, plentiful beaches, and assorted outdoor activities. All boast abundant and varied seafood, from clams to oysters, lobsters, and fish of all kinds, good reason to head to one of America’s oldest states.

We hope these suggestions will inspire you to plan a visit to the northeast this summer. Rustic, luxurious hotels and inns await, and even if you spend more time in an Adirondack chair on the porch than swimming or paddling, you’ll deserve an evening cocktail with sunset at the end of the day.

Woodstock, Vermont

Less than three hours north of Boston in the Green Mountains, Woodstock is an inviting summer destination and a step back in time. Covered bridges over the Ottaquechee River, farmers’ markets, wagon rides, antique shops, and a restored 1890 farmhouse remind visitors of the town’s history dating to its 1761 charter. The Billings Farm & Museum, a working dairy farm features a museum dedicated to preserving the area’s rural history. The Marsh-Billings-Rockefeller National Historical Park, with more than twenty miles of shaded trails, includes a trail to Mount Tom’s peak where hikers are rewarded with a panoramic view of the town. Browse the galleries and unique retail shops or just find a comfortable spot to relax as you enjoy the summer breezes. The luxurious Woodstock Inn & Resort is the ideal place to stay, offering restaurants, golf, tennis, falconry, and biking. Or join a Duvine guided bike tour to explore the area’s scenic roads and towns with The Woodstock Inn as your home base.

Barnard, Vermont

This small Vermont town, surrounded by hills and set near the shores of Silver Lake, is a summer destination made for both relaxation and activity. Silver Lake State Park offers boating, fishing, paddle boarding, kayaking, swimming, hiking, and camping. Barnard’s farming community ensures a bountiful supply of fresh fruits, vegetables, dairy products, and meats, so feasting in the town’s cafes and restaurants is a treat. The Appalachian Trail passes through Barnard for visitors who want to experience a bit of the storied path. Summer theater, art galleries, outdoor live music, and touring show and dance companies provide entertainment in Barnard and nearby towns. Vermont’s only five-star resort and an American Express Fine Hotel & Resort property, Twin Farms, would make for a splendid summer visit with its customized dining, wines, spa, fitness center, and activities arranged for your pleasure, plus its 300 woodland acres. Swimming in Copper Pond, soaking in the Japanese Furo at 104 degrees, or luxuriating on your screened in porch are just a few of the ways to enjoy Twin Farms.

Chebeague Island, Maine

Want to really get away? This island off the coast of northern Maine in Casco Bay could be just the place to wind down and relax. About an hour on a ferry or water taxi from Portland or a shorter trip from Yarmouth, takes you to this small island where the population has increased during summers since the days when early Native Americans sailed there to stock up on fish and shellfish. Today’s summer visitors also enjoy the fresh seafood, along with bicycling around the island, playing golf, swimming at beaches, napping on porches, and trying to capture perfect photos of colorful sunsets. The cozy Chebeague Island Inn, built in the late 1880’s and restored in 2004, offers comfortable rooms, fine dining, lawn games, but no TV, alarm clocks, or room telephones. No worries—your withdrawal from civilization doesn’t have to be complete—there’s free WiFi. They also have L. L. Bean bicycles to borrow, a chef’s garden to explore, and local art to enjoy. If there’s time on your way home, stop in Portland for shopping, nightlife, and a visit to Maine’s oldest lighthouse, the 1791 Portland Head Light. Stay at the historic Press Hotel and treat yourself to their Penthouse Suite for a great experience.

Kennebunkport, Maine

Billing itself as a year-round destination, Kennebunkport is especially lovely in summer when visitors head for beaches, boats, and the pleasures of browsing its shops, galleries, and restaurants. With the Atlantic Ocean and Kennebunk River, there’s plenty of water around, and touring by boat is a great way to appreciate the coastline. Visitors can also learn about where those delicious lobsters are found and how lobstermen bring in the crustaceans that are so much a part of New England vacations. Its location led to Kennebunkport’s history as a shipbuilding and seafaring town, and elaborate mansions built by sea captains can still be seen today in styles of Victorian, Italianate, and more, many with widow’s walks where wives watched and waited for their husbands to return for a journey at sea. For a perfectly plush visit to the area, the White Barn Inn offers guestrooms, suites, and cottages, along with exquisite dining at the White Barn Inn Restaurant and more casual Bistro. The elegant Captain Lord Mansion bed and breakfast with a day spa and on-site concierge is the place for a romantic getaway in an authentic shipbuilder’s mansion.

Westerly, Rhode Island

Set on the state’s southern shore, this beachfront community is bordered by the Pawcatuck River, which divides Rhode Island and Connecticut. Seven miles of sandy beaches include Misquamicut State Beach and several town and public beaches. Westerly’s location on the ocean and river makes it ideal for water sports like rowing, swimming, surfing, sailing, fishing, and paddle boarding. Historic sites attract visitors, and a favorite destination is the Watch Hill Lighthouse, in place since 1745, and rebuilt several times. Their museum is open three days a week during summer. An old-fashioned amusement area, Atlantic Beach Park, features snacks, games, rides, and a 1915 carousel with its unique “flying horses.” Napatree Point Beach, managed by the Audubon Society and the local fire district, is the place for birdwatching in summer. For a change of scenery from the beach, the Westerly Town Forest’s 2.8-mile trail attracts hikers, runners, and walkers to its shaded dog-friendly trails. The Weekapaug Inn, a Relais & Chateaux property, provides complimentary beach lounges, kayaks, paddle boards, sailboats, pedal boats, and boat tours aboard their electric Quonnie Queen.

Newport, Rhode Island

Ideal summer temperatures, balmy evenings, abundant seafood, sandy beaches, and stunning views have attracted visitors to Newport for well over a hundred years. Wealthy families with familiar names like Vanderbilt and Astor built summer homes there, many of which have been preserved and opened for tours. The Breakers, commissioned by Cornelius Vanderbilt II in 1893, has been designated as a National Historic Landmark. Many of the Gilded Age mansions can be seen from the 3.5-mile Cliff Walk, a popular attraction for its ocean views as well. The Scenic Ocean Drive or Ten Mile Drive is another way to see Newport. With more than 400 miles of coastline, visitors have their choice of beaches, some with ocean waves and others calmer waters. Tour Newport from the sea on an America’s Cup yacht, sailboat, lobster boat, or motor launch for another view of its shores, or just stroll around the harbor to ogle the opulent yachts. The International Tennis Hall of Fame, the Audrain Automobile Museum, and Fort Adams State Park are on many visitors’ itineraries. Stay in one of the twenty individually designed guestrooms in a historic mansion at the Chanler at Cliff Walk for comfort and atmosphere in an ideal location.

Narragansett, Rhode Island

A more laid-back summer town, Narragansett is popular with surfers and beach lovers who head for Narragansett Town Beach, Salty Brine Beach, Roger Wheeler State Beach, or Scarborough State Beach, with its boardwalk, bathhouse, concessions, barbecue grills, and hiking trails. Fishing, both onshore and on charter boats, is available, and visitors can rent jet skis, kayaks, or canoes to paddle down the Narrow River. Point Judith Lighthouse, still a navigational aid, was first lit in 1857. Also testifying to the town’s history are The Towers, the remains of the Narragansett Pier Casino, a lively resort during the 1880’s that featured boating, billiards, tennis dancing, and dining. Today, only the renovated granite towers remain after fires and storms destroyed many of the buildings. Visitors can learn more about the area’s history and culture in the South County Museum, with its demonstrations of farming, blacksmithing, carpentry, and textiles. Seafood shacks include the nearly century-old Aunt Carrie’s, known for clam cakes, oysters, and chowder. The boutique Break Hotel, featuring ocean views and retro-surf style, is luxurious and fun. Take advantage of their complimentary beach chairs and bikes, and watch the sunset from their rooftop bar.

Lake Winnipesaukee, New Hampshire

Set against the White Mountains, New Hampshire’s largest lake is one of the state’s most popular year-round destinations. In summer, boating, swimming, and activities in the lake’s eight surrounding towns keep visitors as busy as they wish, although many choose lazy days and scenic views from a chair on the beach or porch. Exploring the 72-square mile lake with its 264 islands and inlets is a favorite activity, and for the adventurous, there are zip lines and mountain bike trails, some with a lift to the top. Take an old-fashioned train ride aboard the Winnipesaukee Scenic Train along the lake’s western shore. For more nostalgia, see a film at the Weirs Drive-in Theater or cruise the lake on 19th-century paddleboat replica Winnipesaukee Belle or the elegant MS Mount Washington. Families will enjoy a visit to Funspot, the largest arcade in the world, offering classic games, bowling, bingo, mini golf, restaurant, and tavern. A range of lodging is available on the lake and in the towns, and for a luxurious stay, Mills Falls Church Landing in Meredith offers rustic elegance, private lakefront balconies, fireplaces, down bedding, beach access, pools, fitness center, and full-service Cascade Spa and Salon.

Mystic, Connecticut

Once a shipbuilding center and now one of Connecticut’s top vacation spots, Mystic is located on the Mystic River along the coast, across Long Island Sound from the eastern tip of Montauk, Long Island. Just about 100 miles from Boston and 140 from New York City, Mystic is an easy weekend escape from the city. Mystic Seaport takes visitors back to the town’s 19th century past, with a stroll through the Mystic Seaport Museum’s village, a recreation with real shops and businesses from the 1800’s. Craftspeople, including shipsmiths, coopers, carvers, and riggers demonstrate their trades, while historians and storytellers describe the past. The Mystic Aquarium features a main gallery with thousands of colorful fish, and the Weird and Wonderful exhibit includes a Giant Pacific Octopus and Giant Japanese Spider Crabs in a live coral reef. Shark encounters, jellyfish, sea lions, whales, penguins, and more are presented in a lively and appealing space. Explore downtown Mystic’s historic sea captains’ homes, churches, and landmarks like the Mystic Drawbridge. Tours and cruises are available, or rent a kayak or paddleboard to explore on your own. Stay in town at the Spicer Mansion, built in 1853 and opened in 2016 after years of renovation. Its eight impeccably decorated guestrooms, fine dining restaurant, and amenities promise a luxurious stay in keeping with the historic atmosphere of the town.

Chatham, Massachusetts

This town on Cape Cod’s southeastern tip is a destination for its beaches, scenery, history, and summer activities. Chatham Lighthouse Beach is one of the most popular, with sandy shores and the Atlantic’s waves and currents. The lighthouse, referred to as Chatham Light, is still in use, dating back to Thomas Jefferson’s appointment of its first lighthouse keeper. A short boat ride away, Monomoy National Wildlife Refuge is a habitat for migratory birds, providing opportunities for visitors to observe at least 25 species of seabirds and shorebirds. Hiking, fishing, shellfishing, and wildlife viewing are permitted among natural habitats that include sand dunes, salt marsh, freshwater ponds, and ocean beach. Baseball games and summer evenings pair well, and Chatham has one of the best collegiate summer leagues in the country. Local theater, walking tours, boat rides, and browsing quaint shops keep visitors entertained. The fully restored Godfrey Windmill is open for tours and actually grinds grain just as it did more than a hundred years ago. The Chatham Bars Inn offers its own quarter-mile beach, pool, spa, and eight-acre farm for the freshest produce to serve with just-caught seafood. Sail around the harbor aboard “Stars and Stripes,” their French-built sloop or shuttle to a barrier beach along the Cape Cod National Seashore.

Edgartown, Massachusetts

Located about six miles off the coast of Cape Cod on Martha’s Vineyard, Edgartown is accessible by ferry, boat, or plane. Its past as a whaling town is still evident in well-preserved 18th- and 19th-century sea captains’ houses, its historic Edgartown Harbor Light, and Village Historic District. Stroll or bike through town at your own pace to enjoy the blend of modern and vintage buildings. An architectural walking tour of the town includes stops at homes dating to the 1600’s and 1700’s as well as the Old Whaling Church still in use as a performing arts center. More recently, Edgartown appeared as the town of Amity in the 1975 film Jaws. Popular South Beach, free and open to the public, faces the Atlantic Ocean on one side and calm waters on the other. Other island activities include fishing, surfing, kayaking, paddle boarding, parasailing, and windsurfing. The Harbor View Hotel, originally opened in 1891, has recently reopened after major renovations, still retaining its classic style and beauty. Dine at the elegant Bettini Restaurant or enjoy a cocktail and tapas at Roxana Bar.

Boston, Massachusetts

If your New England vacation plans involve more of a city atmosphere and less beachy surroundings, that’s fine too. Boston has much to offer summer vacationers, with the Red Sox in town at fabled Fenway Park, harbor boat rides, historic locales, waterfront views, and top hotels and dining spots. A walk on the Freedom Trail at any pace you choose takes you to Faneuil Hall, the Paul Revere House, Bunker Hill Monument, and other historic sites, starting from Boston Common. For more history, visit the Boston Tea Party ship and Museum where you can actually toss tea overboard for your own tax rebellion of sorts. The Museum of Fine Arts, Boston Public Library main branch, Institute of Contemporary Art, and JFK Presidential Museum and Library are other venues you may want to add to your itinerary. For a bit of time away from the city, take a ferry to the Boston Harbor Islands or stay in town and paddle down the Charles River. Pick a neighborhood to walk through, perhaps the North End’s Italian section or Harbor area. Then treat yourself to a stay at the sumptuous American Express Fine Hotel & Resort Property, Mandarin Oriental, Boston, or the Envoy Hotel, with harbor views and rooftop bar. One of Boston’s newest resorts, the Encore Boston Harbor, includes a gambling casino and fifteen dining outlets.


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