Woodstock, Vermont. Image credit MindStorm via Shutterstock

12 Most Charming Towns in New England

New England boasts one-of-a-kind charm with nautical experiences amidst the American atmosphere, and fall foliages unparalleled anywhere else in the world. The coastal region spreads over six northeastern states and includes countless shining gems along the shores that lucky residents call home. These charming towns immerse visitors in the scenic romance of the attraction-laden landscapes, endless water views, and historical sights galore.

Camden, Maine

View from Mount Battie overlooking Camden harbor, Maine
View from Mount Battie overlooking Camden Harbor, Maine. Image credit Leena Robinson via Shutterstock

The town, sitting picturesquely along the MidCoast, is the epitome of modern coastal life with the essence of traditional Maine charm. Camden’s historic streets are laden with brick buildings and architecture such as massive Victorian mansions, all the way to the scenic harbor with renowned Maine views. The working harbor includes handsome sailboats, classic windjammers, and old schooners.

Camden is a popular destination getaway for artists and photographers, while the active head to the town’s surrounding rolling landscape. It smoothly transitions into highlands and mountains where seamless cascades flow down to the water’s shore, in a complete scenic overload.

Concord, Massachusetts

Old North Bridge, Concord, Massachusetts
Old North Bridge, Concord, Massachusetts. Image credit Christian Delbert via Shutterstock

Known for its historic charm, Concord had a focal role during the early days of the Revolutionary War. The charming town was also home to some of America's most-notable literary giants such as Ralph Waldo Emerson, Louisa May Alcott, and Henry David Thoreau.

Concord is a magnet for creatives and sight-seekers on a getaway looking for inspiration through scenic views and history. The town with a welcoming vibe and cozy streets boasts Walden Pond with picturesque shores for recreation and relaxation. The Colonial Inn dating back to 1716 tends to guests with modern rooms and amenities, set conveniently a stone's throw away from must-visits in-town and nature's gateway.

Damariscotta, Maine

Damariscotta, Maine harbor Mid Coast Maine
Damariscotta, Maine harbor Mid Coast Maine. Image credit Anthony F Battista via Shutterstock

The postcard town of Damariscotta is often overlooked for its northern neighbor, Wiscasset. Surrounded by salt marshlands of preserves and oyster beds the charming landscape spreads along the midcoast of Maine. The village’s quaintly-historic downtown induces nostalgia with brick architecture and a vibrant thoroughfare. The Main Street is perfect for strolls right off a storybook cover, overlooking the harbor with vast water views.

There is a decidedly forward-minded food scene in town, while fall time brings about the infamous Pumpkinfest and Regatta to the scenic locale. The oddball, yet charming race comprises 400 to 700-pound, hollowed-out pumpkins, riskily navigated by local "pilots" with paddles and motors. Their awkwardly-masterful piloting down the Damariscotta River during high tide to boast the first prize is a must-see spectacle.

Essex, Connecticut

Waterside houses among trees with boats moored to wooden jetties on a clear autumn day along the Connecticut River, Essex
Connecticut River, Essex. Image credit Albert Pego via Shutterstock

The unique New England town set along the banks of the Connecticut River is full of bucolic charm. Essex boasts a beautiful harbor that justly rates the town among the US’ best. Its charming landscape dotted with cozy inns and historic architecture appears locked in time from the heyday of ship-building prosperity. Settled in 1664, the town includes landmarks such as the Connecticut River Museum. 

Essex downtown and Main Street are whitewashed with tightly-packed houses in a Colonial and Federal-style galore that is a sight to see. Nautical lovers, historians, and the artsy types adore the town for its views and attractions to pass the time. The Griswold Inn, one of the nation's oldest boasts a delicious Sunday breakfast, while the Goods and Curiosities is a cute shop to stock up on history-themed trinkets for the house. There is also the famed Essex Steam Train and Riverboat, comprising a 2.5-hour dual-mode travel through the countryside for varied vistas, such as farms, inlets, and coves.

Exeter, New Hampshire

The river front buildings of Exeter, New Hampshire
The riverfront buildings of Exeter, New Hampshire. Image credit MindStorm via Shutterstock

Many know this charming town for the infamous private school, the Phillips Exeter Academy. The highly reputable institution appears on TV and in movies, along with the town's charming landscape. Students greatly enjoy the vast assortment of mom-and-pop shops veiled in a nostalgic vibe, alongside modern restaurants and art galleries to stay full and cultured between classes.

The new school year brings out the best fall foliage in the state, and arguably the whole country. Its warm glow embraces the campus and complements Exeter's cozy streets. The Exeter Inn offers a quintessential New England overnight experience amidst stately trees and a romantic courtyard crowned with elegant architecture, a stone's throw away from the Academy.

Gloucester, Massachusetts

Gloucester Fisherman's Memorial, Massachusetts
Gloucester Fisherman's Memorial, Massachusetts. Image credit Wangkun Jia via Shutterstock

The charming Massachusetts enclave is America’s oldest working art colony, just a short drive or train ride from Boston. America's oldest seaport, Gloucester was named after the town in England, with the first British settlers arriving from Dorchester, in 1623. Today, tourists enjoy easy access to nautical charm and history veiled in a small-town atmosphere. It is a highly demanded summertime getaway for spectacular beaches and waterside strolls with old lighthouses.

The lovely waterfront main attraction is a promenade strewn with opportunities for deep-sea fishing, and whale watching, and aligned with delightful restaurants. You can have a waterfront view for every meal of the day while dining on some of the freshest seafood in the US. The waterfront is also within walking distance of all the town's rich offerings in art, culture, and many historical sites.

Hancock, New Hampshire

Summit views from Mount Monadnock in New Hampshire
Summit views from Mount Monadnock in New Hampshire. Image credit Monika Salvan via Shutterstock

Stepping into this charming small town in southern New Hampshire is like walking out of a time machine two centuries ago. The streets exude a magical olden-day aura amidst the most-delightful collection of historic buildings and architecture, such as Hancocks’s heart of the 1820 meeting house. The magnificent church is one of the best, meticulously-preserved examples in the entire US, while the whole main thoroughfare boasts a spot on the National Registry of Historic Places.

Hancock boasts big attractions to its name for complete immersion in the deep culture and history of the small town. Follow the sounds of the authentic Revere and Son’s bell, chiming every hour, day and night. For a complementing stay, New Hampshire's oldest, the Hancock Inn, is one of the oldest B&Bs in all of New England. It opened six years after the Revolutionary War in 1789 and continues to exceed guest expectations with impeccable service and delicious meals amidst modern amenities.

Newport, Rhode Island

The historic seaside city of Newport, Rhode Island
The historic seaside city of Newport, Rhode Island. Image credit George Wirt via Shutterstock

Newport is the shining star along Rhode Island’s scenic coast and one of New England's most-precious gem towns. It is a beloved and easily accessible getaway for all interests of pursuit with a year-round bustling waterfront downtown, wondrous architecture, and open views. The historic port was once a playground for the nation's wealthiest who could afford then-expensive amenities with expansive vistas along the shore. The notable Gilded Age mansions reminiscent of European palaces are open for a stroll through history today.

Newport evolved with plentiful and affordable modern amenities for the everyday traveler on a weekend escape, including three vineyards for wine enthusiasts. Its magnificent seaside aligned with fine-dining establishments is nation-renowned for the best yachting. History fans and sight-seekers enjoy visiting many fascinating museums and historical sights and spotting the distant old lighthouses.

Oak Bluffs, Massachusetts

Aerial view of Oak Bluffs, Martha’s Vineyard
Aerial view of Oak Bluffs, Martha’s Vineyard. Image credit Megan.10 via Shutterstock

The town of Oak Bluffs is a truly-quintessential find along Martha’s Vineyard island’s northeastern shore, dotted with hundreds of colorful gingerbread cottages. The collection of unique houses exudes a fairy-tale atmosphere that often decorates the pages of travel magazines. This picture-perfect harbor started as a Methodist campground in the 1800s, evolving from canvas tents to the elaborately-decorated galore today. The attractive village became a tourist magnet in its own right in the late 19th century and thousands continue to seek out a weekend escape into an explicit burst of scenery.

The lucky residents enjoy easy beach access for everyday pursuits and quick travel to the mainland via ferry. The expansive shoreline with beaches facing into Vineyard Sound is also known for minimal surf (and great turf). Following a day of swimming in the calm waters where kids enjoy wading the shallows, it is imperative to try local cuisine that complements the wine scene. The postcard town is an incredible family destination, including a scenic ferry-in, and a ride on the nationally-landmarked Flying Horses Carousel, the oldest in the US. The charming attraction is a must-experience for all ages, spinning every year since 1876 from Easter Sunday through Columbus Day.

Siasconset, Massachusetts

Sankaty Lighthouse in Siasconset on Nantucket Island, Massachusetts
Sankaty Lighthouse in Siasconset on Nantucket Island, Massachusetts. Image credit Gretchen Blair Madden via Shutterstock

The town of Siasconset with a mystic name is a charming Nantucket enclave on the storied island. It is the epitome of freedom from a concentrated metropolis. The sweeping panoramas into the deepest blue of the Atlantic Ocean hypnotize for endless strolls, with only the Sankaty Head Light breaking the immense scenery.

Check out the rows of classic New England saltbox houses along the shores while sailing, followed by a stroll to admire the tasteful beach peas and rose gardens surrounded by white-picket fences. The island's most-scenic Sconset Bluff Walk is a popular hike along the coast with delightful views. It is an excellent way to enjoy some exercise and clear the mind with sights easy on the eyes, heading north from the village to a scenic lighthouse.

Sugar Hill, New Hampshire

Scenic view from Sugar Hill, New Hampshire
Scenic view from Sugar Hill, New Hampshire. Image credit Jerry Gantar via Shutterstock

With only about 500 year-round residents and the name Sugar Hill, the delightful village cannot get any more charming. The little New Hampshire town boasts a picturesque and quaint spot in the shadows of the beautiful White Mountains. The tiny Sugar Hill is a vision of beauty that leaves a big impact with wholesome attractions and picture-perfect landscapes. Its cozy streets are strewn with places to sit and admire the views, along with a local country store selling made-from-scratch cheddar cheese.

The justly-named Sunset Hill House offers sweeping views of the White Mountains from the windows and terrace, with unforgettable sunsets. The charming town also boasts access to the world’s oldest golf course of nine holes, alongside a pool, and pristine gardens for fresh-air strolls and relaxation.

Woodstock, Vermont

Woodstock, Vermont
Woodstock, Vermont. Image credit Eric Urquhart via Shutterstock

Woodstock is the county seat of Windsor County and encompasses five hamlets in addition to the village, along the scenic banks of the Ottauquechee River. The village with under 3,000 residents includes Georgian, Federal, and Greek Revival homes. It is the epitome of the mid-19th century charm, from when Woodstock was first settled along the waters. Today, the old-Americana atmosphere and quintessential New England vibe blend in picture-perfect sights such as a covered bridge, old pretty parks, village green, and surrounding country farms.

The lush townscape with year-round wander-worthy streets becomes especially cozy during autumn's embrace of fall foliage. After a stroll through the historic streets with beautiful homes and buildings, the nearby Sugarbush Farm has the best selection of fresh cheeses and locally-made maple syrups.

These quintessential towns in New England emanate local charm amidst stunning nature. The sweeping water views and deep history induce nautical nostalgia, so pick your closest enclave for a guaranteed delightful experience on a quintessential getaway.

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