Historic downtown buildings in Ogunquit, Maine. Image credit Wangkun Jia via Shutterstock

9 Unforgettable Small Towns to Visit in New England

There is no better place to discover exactly what it's like to live out those small-town dreams than in New England. Comprising of Maine, Vermont, New Hampshire, Massachusetts, Connecticut, and Rhode Island, this northeastern region of the United States is home to some of the most stunning fall foliage and forested mountains. For visitors searching for an unforgettable trip that mixes the glory of New England with that cozy small-town feel, make sure to check out these destinations.

Woodstock, Vermont

Overlooking a peaceful New England Farm in the autumn at early morning, Woodstock, Vermont
Woodstock, Vermont, in autumn.

One of the most picturesque towns in the area, Woodstock, Vermont, has a population of around 3,000 people and has been named the "quintessential New England village." It comes alive during the months of September and October, with bridges and hills covered with brightly colored leaves, but offers an unforgettable experience during any time of the year. Tourists flock to the iconic Taftsville Covered Bridge or drive to one of the nearby farms and sample local cheeses and maple syrup. There is also the family-friendly Saskadena Six ski slope and a few skating rinks located in the town for more active visitors during the wintertime.

Bar Habor, Maine

Rocky coast and view of boats in the harbor at Bar Harbor, Maine.
Boats in the harbor at Bar Harbor, Maine.

Welcome to the gateway of Acadia National Park, where tourists will be able to witness the gorgeous views of Frenchman's Bay. Bar Habor lies in Maine's southern area and has attracted many visitors during the summer, starting all the way from the 19th century. It is also home to Cadillac Mountain, the highest point on the eastern seaboard and often where you can catch the first rays of sun in the early morning.

Essex, Connecticut

Antique train at Essex Train Station in Essex, Connecticut.
Antique train at Essex Train Station in Essex, Connecticut.

Located halfway between Boston and New York City, Essex is a small town many look past. With a population of approximately 6,500, this hidden gem is made up of Essex, Centerbrook, and Ivoryton — three small villages that each have its own charm. While Essex specializes more in its natural landscape and man-made architecture, Ivoryton holds years of history in its churches, factories, and Victorian-style houses, and Centerbrook is generally considered the more commercial part of Essex.

Stowe, Vermont

Iconic church in Stowe, Vermont with fall colors.
Autumn in Stowe, Vermont.

Located in northern Vermont, Stowe is heaven for those who love skiing or snowboarding. This small town is often known as "The Ski Capital of the East," where visitors can hit the slopes of Mount Mansfield and Spruce Peak. But just like any other New England town, Stowe isn't just a great destination during the wintertime. On warmer days, the town offers gondola rides up to the mountains or traveling along the historic Toll Road. During the fall, Stowe comes alive, as well, where tourists can buy pumpkins and take part in harvest festivals or marvel at the autumn scenery with a drive or stroll along Stowe Recreation Path.

New Shoreham, Rhode Island

Block Island North Light Lighthouse in New Shoreham, Rhode Island.
Block Island North Light Lighthouse in New Shoreham, Rhode Island.

New Shoreham is the smallest town in the smallest state in the United States — and that is a good enough reason for some tourists to visit this stretch of land. The municipality encompasses the entire area of Block Island, an island around 12 miles south of mainland Rhode Island, and is characterized year-round for its beach roses, 300+ freshwater ponds, two man-made harbors, 17+ miles of coastal beach, and 30+ miles of hiking trails. It may be a very small town, but it's an ideal getaway for travelers who are looking to be more active in an unforgettable destination.

Williamstown, Massachusetts

Aerial view of the Thompson Memorial Chapel on the campus of Williams College in Williamstown
Overlooking Williams College in Williamstown, Massachusetts.

Located in Berkshire County in the northwestern corner of Massachusetts, Williamstown is a place rich with history. The bustling town was originally settled in the mid-1700s and established by English colonists as a buffer against greedy Dutch settlers. The name "Williamstown" comes from Ephriam Williams, who was a British soldier and land owner who lost his life in the French and Indian War. This entire history is at the Williamstown Historical Museum, which takes guests on a journey from pre-colonial times to the present day.

Stockbridge, Massachusetts

Spring flowers blooming along a walkway in Stockbridge, Massachusetts.
Spring in Stockbridge, Massachusetts.

About a 2-hour drive from Boston, the small, quiet town of Stockbridge is a great getaway to relax and spend some time away from the city. One of its most popular attractions is the Norman Rockwell Museum, located in the center of Stockbridge. It features the late Norman Rockwell, where tourists are able to see the studio where he worked and lived. There are also the Berkshire Botanical Gardens or the Naumkeag Mansion and Gardens for visitors who may want to spend time outside.

Bristol, Rhode Island

Historic Blithewold Mansion, Gardens and Arboretum in Bristol, Rhode Island.
Historic Blithewold Mansion, Gardens, and Arboretum in Bristol, Rhode Island. Image credit: Faina Gurevich via Shutterstock.com

Bristol may have a larger population of around 22,000, but that doesn't take away its charming small-town feel. It is in Bristol County, which is made up of Warren, Barrington, and Bristol. This hidden gem was one of five state capitals until 1854 and is home to many historic landmarks, such as the Joseph Reynolds House from 1698. The town also hosts the iconic Annual Fourth of July celebration — a tradition that has been practiced since 1785.

Ogunquit, Maine

Fall colors and boats in Perkins Cove, Ogunquit, on the coast of Maine.
Perkins Cove, Ogunquit, on the coast of Maine.

With the holidays fast approaching, Ogunquit is the place to go for visitors dreaming of a white, wondrous Christmas. Popular during the holiday season, this quaint little town mostly draws travelers in with its promising summer scenery, but December is a special time for Ogunquit. Its event, "Christmas by the Sea," is a unique experience with a bonfire by the beach, fireworks, concerts, craft shows, and visits with Santa. With its decorative lights and cold weather, there is no doubt this small town is a great place for a calming yet unforgettable Christmas vacation.

New England In All Its Glory

New England may be known as the best place to witness fall foliage with its larger cities such as Boston, Worcester or Providence, but there are many unforgettable small towns within that offer a wide array of great activities all year round. For visitors who just want to wind down and escape the feeling of a big city for a while, these destinations can provide just that.

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