The Most Beautiful Towns in New England

Portland Light Head, built in 1791, sits at the entrance of Portland harbor in the Gulf of Maine
Portland Light Head, built in 1791, sits at the entrance of Portland harbor in the Gulf of Maine | © lucky-photographer / Alamy Stock Photo
Photo of Veronika J Spencer
28 July 2021

New England is one of the most beautiful parts of the United States, brimming with small, pretty seaside towns. Here’s our guide.

Visitors will fall in love with the spectacular scenery in Newport and Martha’s Vineyard, the historic buildings and museums of Lenox and Portsmouth, tasty seafood in Brattleboro and Gloucester and the many unique cultural activities found in these incredible towns. It is no wonder that many of these small towns are favorite living and vacation choices of the wealthy. In the summer months, visitors from all over the world come to see and enjoy all that New England’s lovely towns have to offer. Here is a list of the most beautiful towns in New England.

Newport, Rhode Island

Museum
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Castle Hill Lighthouse bathed with the warm glow of sunset, Newport, Rhode Island
© Dawna Moore / Alamy Stock Photo

Newport, Rhode Island, is one of the shining gems of New England. This spectacular coastal town is rich with architectural wonders and a bustling waterfront downtown. A popular weekend getaway spot, Newport was once a playground for the incredibly wealthy, and visitors can now tour the famous Gilded Age mansions that were modeled on European palaces. With three vineyards, Newport is an ideal destination for wine enthusiasts. Its magnificent seaside also makes it one of the top destinations in the US for yachting. In addition to the finer things in life, Newport also offers a range of historic sites, lighthouses and fascinating museums that are definitely worth a visit.

Kennebunkport, Maine

Natural Feature
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A large mansion reflecting off the waters of the Batson River in Kennebunkport Maine on a cold sunny winter day.
© Dan Hanscom / Alamy Stock Photo

Kennebunkport was settled in the 1600s as a ship-building town for many years, and wealthy sea captains built impeccable mansions on the beautiful Maine Coast. Today, many of these mansions have been converted into lovely inns that are perfect for relaxing weekend getaways. Visitors to Kennebunkport will find exciting activities to take part in at any time of year. Whale watching and sailing excursions are popular summer activities, as are visiting the natural wonders of Blowing Cave, Spouting Rock and Goose Rocks Beach. Kennebunkport is also known for being the summer residence of President George HW Bush.

Lenox, Massachusetts

Architectural Landmark, Historical Landmark
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Lenox, Massachusetts USA
© Prisma by Dukas Presseagentur GmbH / Alamy Stock Photo

Lenox is a small town nestled in Western Massachusetts and is a thriving cultural destination in New England. It is home to the Shakespeare and Company’s international campus and the Boston Symphony Orchestra in the summer months. Art lovers can find an excellent collection of American and European cubist art at the Frellinghuysen Morris House and Studio, and history buffs will enjoy the many fascinating museums that Lenox has to offer. Edith Wharton’s mansion, the Mount, is also a popular destination as it is one of the finest restored New England mansions from the Gilded Age.

Portsmouth, New Hampshire

Natural Feature
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Scenic town, Portsmouth, New Hampshire, USA
© Mira / Alamy Stock Photo

Portsmouth was settled in 1623 and is the third oldest city in the US. This long history has contributed to the charm of the town, and offers visitors many fascinating historical sights to see. The streets are filled with colonial, Georgian and Victorian architecture and there are plenty of museums to explore. The Strawbery Banke Museum offers visitors a glimpse into the colonial past of the city through a 10-acre (4ha) living history museum, and the famous tug boats on the Piscataqua River are also a must-see when visiting Portsmouth.

Brattleboro, Vermont

Architectural Landmark, Historical Landmark
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Beautiful Vermont covered bridge surrounded by colorful fall foliage.
© Littleny / Alamy Stock Photo

Brattleboro is a unique town with a lot to offer. It is the only town with that name in the entire world and it prides itself on being one-of-a-kind. This town is a great place to be in the winter as hiking, skating, cross-country skiing and snowmobiling are all popular activities. For those who prefer the arts, there are many fantastic local bands, an excellent local theater, and a museum and art center with year-round exhibitions. The edgy downtown hosts a number of unique shops to visit and a large range of dining options.

Mystic, Connecticut

Architectural Landmark, Historical Landmark
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Harbor View with a Lighthouse and Sailing Ships, Mystic Seaport, Connecticut
© George Oze / Alamy Stock Photo

The small town of Mystic, Connecticut, is one of New England’s most delightful towns. Visitors can see the only beluga whales in New England at the Mystic Aquarium, and be delighted by the sight of tall ships in the Mystic Seaport. A stroll through downtown Mystic will uncover a number of one-of-a-kind shops, the landmark Bascule Bridge, a number of unique dining options and the Olde Mistick Village. For those feeling lucky, there are two exciting casino resorts located nearby, while Mystic itself is home to many cultural and historical museums.

Martha's Vineyard, Massachusetts

Natural Feature
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Historic Gay Head Lighthouse, Martha's Vineyard, Massachusetts
© Cindy Goff / Alamy Stock Photo

Martha’s Vineyard, just south of Cape Cod, is known as an affluent summer getaway destination. The third-largest island on the East Coast of the US, it’s accessible only by boat or air. More than half the houses here are only occupied seasonally and the population of the island increases six-fold in the summer months. There are six small towns here that each have their own charms and make Martha’s Vineyard a great destination to visit. The summer weather is pleasant, the scenery is incredible and the large range of activities available will keep you entertained.

Bar Harbor, Maine

Natural Feature
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A colorful photo of waterfront houses in Bar Harbor Maine as the seasons begin to change in Autumn.
© Joe Benning / Alamy Stock Photo

Bar Harbor’s location, among soaring granite cliffs and surrounded by Acadia National Park, creates a glorious scene for romance and adventure. Visitors can enjoy the rocky coastline, as well as the nearby lakes and mountains. Bar Harbor is a small town of just over 5,000 that sits on Mount Desert Island and is a New England destination that should not be missed. Like several other beautiful New England towns, Bar Harbor was a popular summer destination for the affluent-elite during the Gilded Age. Today, visitors can enjoy a wide range of activities including, biking, kayaking, hiking, fishing, snowmobiling, visiting museums or taking lighthouse tours.

Montpelier, Vermont

Architectural Landmark
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© Sean Pavone / Alamy Stock Photo

Montpelier is the smallest state capital in the US, with a population of only a little more than 8,000 people. Despite its small size, Montpelier has a lively music and arts scene, and many historical attractions to visit. Shopping options and world-class dining are also plentiful in this small city. It is also home to the Vermont College of Fine Arts and the New England Culinary Institute. Visitors will be happy to discover that they have access to all of the amenities of a bigger city, but with small-town charm and amazing outdoor recreational activities available just outside the city center.

Gloucester, Massachusetts

Natural Feature
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United States, New England, Massachusetts, Cape Ann, Gloucester, Annisquam Harbor, autumn
© Hemis / Alamy Stock Photo
Gloucester, Massachusetts is known as America’s oldest working art colony and the original seaport. Just a short drive or train ride away from Boston, Gloucester is an easily accessible and delightful getaway. The waterfront is a main attraction with many opportunities for deep-sea fishing and whale watching. The historic lighthouses and spectacular beaches are also worth a visit. Thanks to its great location, Gloucester has some of the best and freshest seafood in the US and features many delightful restaurants. Whether in search of historical sights, cultural arts or tasty food, Gloucester has it all.
These recommendations were updated on July 28, 2021 to keep your travel plans fresh.

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