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20 Most Picturesque Towns in New England

New England charms visitors with some of the country’s most picturesque scenery, postcard-worthy towns, and luxury hotels. Most travelers flock to this area to see the fall foliage or indulge in incredible seafood, but it’s also a family-friendly area where you’ll discover a long list of things to do. If you’d like to experience some of its prettiest towns, these destinations from Vermont and New Hampshire to Massachusetts and the rocky shores of Maine are sure to be some of the most unforgettable.

Oak Bluffs - Martha's Vineyard, Massachusetts Oak Bluffs on Martha's Vineyard, MA
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Oak Bluffs - Martha's Vineyard, Massachusetts

Oak Bluffs, located on the northeastern shore of Martha’s Vineyard, is known for its unique, vibrant-colored gingerbread cottages that give the town a storybook feel. The picturesque harbor village evolved from a mid-19th-century Methodist campground, and eventually, the canvas tents were replaced with hundreds of tiny, elaborately decorated cottages. They became a tourist attraction in their own right in the late 19th century – many are still family-owned and passed on from generation to generation. In this beautiful New England beach town, you can easily walk off the ferry and spend the day on foot exploring it or visiting the shoreline. The beaches here face into Vineyard Sound and usually have very minimal surf, which makes the water ideal for swimming or letting the little ones enjoy wading. Don’t miss taking a ride on the Flying Horses Carousel – it’s the oldest carousel in the nation, spinning since 1876, and a national landmark.

Woodstock, Vermont Woodstock, Vermont
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Woodstock, Vermont

One of the most charming getaways in Vermont, Woodstock is located on the banks of the Ottauquechee River and home to 3,200 residents that are spread throughout five even smaller villages and hamlets. Settled in the mid-18th century, Woodstock exudes Americana charm as a quintessential New England village with a picturesque covered bridge, old country farms, pretty parks, restored Georgian, Federal, and Greek Revival homes, as well as a village green. While it’s especially stunning in the autumn when the leaves have turned, it’s beautiful year-round. Wander the streets and check out the beautiful homes and buildings in this town that look the same as they did a century ago, and be sure to sample the cheeses and maple syrups at Sugarbush Farm.

Weston, Vermont The old Mill Museum, water wheel, millpond and waterfall in Weston Village in Vermont
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Weston, Vermont

Weston is another lovely Windsor County town that represents the New England countryside at its finest. A village green with a gazebo, family-owned country stores and shops selling Vermont-made clothing and heavenly Vermont fudge, charming B&Bs, and beautiful New England homes helps create this Vermont masterpiece that looks as if you’ve stepped into a Norman Rockwell painting. The entire village is listed on the National Register of Historic Places. Not only will you find a variety of dining experiences, including everything from relaxed bites at taverns to sophisticated eats at upscale restaurants, but Weston also hosts historical museums and theatrical productions.

Mystic, Connecticut Mystic, Connecticut
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Mystic, Connecticut

Mystic, Connecticut is a beautiful coastal town located halfway between New York City and Boston that is home to Mystic Seaport, originally one of the region’s most important seaports, and its history is wonderfully preserved. It includes one of the largest maritime museums in the country, with more than 500 vessels, including the last remaining whaleship in the world. It also hosts an aquarium where you can get up close to penguins, sea lions, seals, and beluga whales, and inland, you’ll find charming Colonial period homes lining Main Street as well as plenty of interesting shops and seafood eateries, including the famous Mystic Pizza restaurant that inspired the 1988 movie of the same name starring Julia Roberts. Stop by the Olde Mistick Village if you’re looking for souvenirs – and you can indulge in delectable homemade fudge at Franklin’s General Store.

Rockport, Maine Rockport, Maine
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Rockport, Maine

Rockport is a quaint town in Maine known for its tranquil and beautiful harbor, where you’ll see grand schooners and fishing boats bobbing up and down. If you’re a seafood lover, check out the restaurants teeming with fresh-caught seafood and other dishes featuring high-quality farm- or sea-to-table ingredients. There are local artisan shops for picking up gifts and souvenirs, and a variety of activities can be enjoyed too, like beachcombing for shells and wading at Walker Park. One of the must-dos is to take a selfie next to the commemorative statue of Andre the Seal, the honorary Harbor Master for some two decades. Andre spent his summers here in the harbor after being released from his winter stay at Boston’s New England Aquarium. A book about him, A Seal Called Andre, was published in 1975, and after Andre’s passing in 1985, a movie was made about him and his influence on the local community.

Bar Harbor, Maine People gathering for Independence Day in Bar Harbor, Maine
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Bar Harbor, Maine

Bar Harbor, Maine is a haven for nature lovers and is known for its beautiful rugged coast and as the home for the majority of Acadia National Park. It gets its name from the famous sandbar that connects Bar Island to the mainland at low tide, which is used by hikers and kayakers as a launching point for exploration. The quaint seaside town is incredibly diverse, offering everything from the sea to the mountains. There are biking and hiking trails throughout the national park, with one of the most popular leading to the top of Cadillac Mountain, where amazing vistas await, as well as canoe and kayak tours along the Mount Desert Island coastline. The Abbe Museum offers the chance to learn about native Wabanaki peoples, and at the 2 Cats Restaurant, not only can you enjoy a meal, but you can purchase cat-themed souvenirs. Of course, you won’t want to miss the chance to dine on the area’s specialty: lobster, which can be found on nearly every corner.

Franconia, New Hampshire Franconia Notch State Park
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Franconia, New Hampshire

Franconia is an ideal place to escape the chaos of the city and enjoy the beautiful outdoors. This tiny, sparsely populated town is home to the Cannon Mountain Ski area and Franconia Notch, a mountain pass with towering mountains that rise as high as 3,000 feet on each side, where visitors will find all sorts of adventures to enjoy, including fishing, canoeing, kayaking, hiking, and biking in the summer months. At this time of year, an Aerial Tramway brings tourists to the top of Cannon Mountain to enjoy the alpine conditions. In the winter, the area makes the perfect base for all types of winter sports and activities. The New England Ski Museum is located next to the tramway and features exhibits on the local aspects of ski history, including several important “firsts” at Cannon Mountain and the career of area native, Olympic gold medalist Bode Miller.

Brattleboro, Vermont Brattleboro, Vermont
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Brattleboro, Vermont

Brattleboro is a picturesque town in Vermont on the corner of three states known for its outstanding farmers’ market, as well as its liberal, counter-culture thinking. It prides itself on being one-of-a-kind and is the only town with its name in the entire world. Brattleboro is a great place to be in the wintertime, offering the chance to go ice skating, cross-country skiing, snowmobiling, and snowshoeing, and indoors you’ll have just as much to do. You’ll find an outstanding local theater, great local bands, a museum and art center as well as a number of unique shops downtown and a wide range of dining options. Area farms are vital to Brattleboro’s economy, and daily life in general, resulting in an outstanding selection at the Brattleboro Farmers’ Market which includes fabulous lunch fare, fresh produce, bread, and pastries.

Stowe, Vermont Stowe, Vermont
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Stowe, Vermont

Stowe has long been a popular ski destination in the Northeast, with many of the area activities revolving around the state’s tallest peak: Mount Mansfield. In the summer and fall, it’s a favorite for hiking, and in the winter, non-skiers and boarders can also enjoy tubing and sleigh rides. But its appeal lies beyond the mountain as the village is postcard-perfect, with covered bridges and church steeples set against the picturesque Green Mountains. Visitors can also stock up on fabulous made-in-Vermont items like cider donuts and maple syrup in addition to sampling delicious cuisine at the many restaurants.

Camden, Maine Camden, Maine

Camden, Maine

This “jewel of the Maine coast” as it’s often referred to, was once a haven for manufacturing but is now mostly known as a popular tourist destination. Camden is so picture-perfect that you might mistake it for a movie set – in fact, it has been used as the setting for several films, including 2001’s “In the Bedroom” and the 1957 drama “Peyton Place.” Sailboats dot the water in Penobscot Bay, and waterside seafood beckons. Simply walking the High Street Historic District to take in classic New England architecture is enjoyable though you can also go sailing around Camden Harbor or hike around Camden Hills State Park. If you visit in early autumn, you’ll be rewarded with the magnificent display of fiery reds, blazing oranges, brilliant yellows, and purple hues of leaf-peeping season.

Exeter, New Hampshire Exeter, New Hampshire
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Exeter, New Hampshire

Exeter is a historic town overflowing with charm. Founded in 1638, it offers appeal to everyone from history enthusiasts and outdoor adventurers to art lovers. A stroll downtown offers the chance to visit attractive buildings with art galleries, restaurants, and shops or view historic homes like the Ladd-Gilman House, now serving as the American Independence Museum, where you can see an original printing of the Declaration of Independence as well as original drafts of the Constitution, on its tree-lined streets. If you’re seeking outdoor recreation, you’ll find hiking and mountain biking opportunities.

Wolfeboro, New Hampshire Wolfeboro, New Hampshire
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Wolfeboro, New Hampshire

Summertime activities are where it’s at in Wolfeboro. Billing itself as America’s “Oldest Summer Resort,” it sits on the eastern banks of Lake Winnipesaukee, featuring whitewashed gateposts, coiffed hedges, and an English-rules croquet club. With its shoreside location, it also offers the chance to take part in every type of water sport imaginable, whether you want to dive in or stay afloat. If you want to stay on land, you might take a narrated trolly tour and then visit the Wright WWII Museum and the New Hampshire Boat Museum, dedicated to all manner of watercraft that figure in the state’s history, before shopping the waterfront’s interesting shops and galleries. When you’re ready to get out on the water but don’t want to get wet, charter the Latitude 43 or head out on MS Mount Washington.

Provincetown, Massachusetts Provincetown, Massachusetts
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Provincetown, Massachusetts

Provincetown, located at the far tip of Cape Cod, is famous for its gorgeous surroundings that include vast sand dunes and over 30 miles of beaches, as well as being a place that welcomes all types of people. It’s long been an art colony – in 1914, artists and business people formed the Provincetown Art Association and Museum to show and collect work by local figures, and it’s also a place where people can go to let loose and be themselves without fear of judgment. Explore the colorful downtown area, which hosts everything from grand mansions and fine eateries to fabulous seafood shacks, fudge shops, art galleries, and bookstores, and enjoy lots of interesting people-watching. Painters and photographers find it irresistible, with the broad arc of the sun creating a diffuse illumination that seduces the eye.

Boothbay Harbor, Maine Boothbay Harbor, Maine
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Boothbay Harbor, Maine

A laid-back village far from busy Route 1, Boothbay Harbor is a picturesque coastal town with a rich history, quaint local shops and boutiques, fabulous dining, and the opportunity for world-class boating excursions. You’ll be enchanted by its authentic charm, a working waterfront, and its tranquil coves, lighthouses, and rocky shores. The village shines with brick sidewalks, hilly terrain, and attractive hand-painted signs, while a 1,000-foot-long bridge connects the east and west sides of the harbor for easy access to all types of fun activities. There are some 25 daily boat excursions that leave right from the harbor, including the chance to enjoy close-up encounters with wildlife like seals, puffins, and whales or sip champagne aboard a romantic sunset schooner. Visitors can also check out the local boatyards to see the tradition of boat building that’s still alive today, and at Boothbay’s Coastal Maine Botanical Gardens, there are 250 acres of gardens and grounds to explore with everything from brilliant flowers to stonework and waterfalls.

Shelburne Falls, Massachusetts Shelburne Falls, MA: Bridge of Flowers
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Shelburne Falls, Massachusetts

The village of Shelburne Falls actually spans two towns, Shelburne and Buckland, both of which offer much to explore. Sightseers flock to the Bridge of Flowers, which stretches over the Deerfield River, connecting the two towns. In 1928, the arched bridge had fallen into disuse, so the Shelburne Falls Women’s Club sponsored a project taking it from visual blight to a public garden. Today, the community continues to work together to keep it in bloom. While the bridge is its claim to fame, you’ll also discover many fine examples of Victorian architecture, delightful shops, and galleries. While you won’t find a Walmart here, you will find lots of local, handmade items. The streets are filled with the energy of artisans that craft hand-blown glass, quilts, and all sorts of more unique, prized goods made by local artisans.

Dorset, Vermont Dorset, Vermont
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Dorset, Vermont

Dorset is a family-friendly, historic community tucked in the hills of southern Vermont that was established back in 1761. It’s well known for its mountains, valleys, and New England village charm. Lined with clapboard homes and divided by green, it feels as if you’ve entered a Thornton Wilder scene. There are a number of elegant inns that offer the chance to hang out on the porch and forget about all of your cares, and of course, you’ll find the requisite general store, which comes complete with a ‘70s-era gas pump. Dorset’s farmers’ market features freshly picked fruits and vegetables, home-baked bread and pastries, grass-fed meat and poultry, artisan cheeses and wines, specialty goods, Vermont crafts, hot prepared foods, live, local music, and more.

Bretton Woods, New Hampshire Omni Mount Washington Resort
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Bretton Woods, New Hampshire

For decades, Bostonians have been escaping the summer heat by fleeing to the natural air conditioning offered by the White Mountains, and in the peak of the Gilded Age, as many as 57 trains arrived daily at the depot in Bretton Woods. In the winter, it’s known as the home of the largest ski area in the state – Ski magazine named it one of the top five ski destinations in the East for snow. The enclave set on an alpine table west of Mount Washington is home to the Omni Mount Washington Resort, one of the last surviving handful of New Hampshire grand hotels, which includes two golf courses, alpine and Nordic skiing, a massive spa, sled reds, dog sled adventures, horseback riding, tennis and more. When the hotel opened in 1902, it was the culmination of a series of ever grander White Mountains hotels, and today, it’s the most luxurious survivor from those golden days – sink into a wicker armchair on its 900-foot veranda and gaze at a glorious sunset.

Hancock, New Hampshire Hancock, New Hampshire
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Hancock, New Hampshire

Hancock is a small town in southern New Hampshire that is a veritable time machine into the past, with most of its buildings that line the main street on the National Registry of Historic Places. Hancock considers its 1820 meeting house, known as one of the best Federal-style churches in the state, to be its heart. The meeting house is home to an authentic Revere & Son’s bell, which chimes on the hour, day and night. To truly immerse yourself in the town’s history, stay at the Hancock Inn, the oldest inn in the state and one of the oldest B&Bs in New England. It began offering accommodation and meals to travelers in 1789 – just six years after the Revolutionary War was over.

Sugar Hill, New Hampshire Saint Matthew's chapel in Sugar Hill, New Hampshire
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Sugar Hill, New Hampshire

On the opposite end of the spectrum, Sugar Hill is one of New Hampshire’s youngest towns, incorporated only a little over a half-century ago in 1962. Nestled in the White Mountains, it’s become popular for romantic getaways, fall foliage, and opportunities for outdoor adventure. Located near a number of ski centers, the town makes a perfect base for a winter escape with the chance to enjoy alpine and cross-country skiing, snowboarding, and snowshoeing. In the summer, ride the cable car up Cannon Mountain and hike the observatory trail, or take the Cog Railway to the top of Mount Washington to take in the view from New England’s highest peak. While in town, start your morning off right at Polly’s Pancake Parlor with homemade pancakes topped with famous New Hampshire maple syrup, and be sure and check out the Sugar Hill Historical Museum, which features a sleigh that once belonged to actress Betty Davis.

Wiscasset, Maine Wiscasset, Maine in the late fall
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Wiscasset, Maine

Situated just under 45 miles from Portland, Wiscasset overlooks the Sheepscot River and has managed to retain much of the charm that represents quintessential Maine and New England, with old lovely churches and magnificent historic homes. There are interesting sites on nearly every corner, including some of the region’s most famous architectural landmarks, like the Nickels-Sortwell House on Main Street with its Federal-style architecture, an elliptical stairway with rope-like carvings and a beautiful oval skylight. The Castle Tucker is a Victorian-style mansion known for its upstairs piazza which overlooks the river. Right downtown, you’ll find wonderful shops and antique stores, restaurants and attractions, like the 1812 Jail.

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