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The Quaintest Small Towns to Visit in New England


The small town of Mystic, Connecticut, was made famous in the 1988 flick “Mystic Pizza.”

mystic connecticut

Mystic, Connecticut.


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Population: 4,249

There are tons of things to do while visiting, including visiting the Mystic Aquarium or grabbing a slice at the real-life Mystic Pizza restaurant.

Mystic also comes alive around the holidays, when visitors can stroll around the town’s harbor, look at decorated sailboats, and stop in for some holiday shopping on the town’s main street. 

Camden, Maine, is described as the “Jewel of the Maine coast” and is famous for its harbor and shopping district.

main street Camden, Maine

Camden, Maine.

Kristi Blokhin/Shutterstock


Population: 4,850

The small seaside town is home to antique shops, plenty of seafood restaurants, cafés, and the Camden Public Library, which overlooks the water.

In the summer, visitors can spend time at Barret’s Cove, a freshwater beach on Megunticook Lake, go sailing, grab a lobster roll at one of the many downtown restaurants, or tour one of the town’s lighthouses. Around the holidays, the town is just as festive, with colorful light displays and its annual “Christmas by the Sea” festival.

York, Maine, is famous for its beautiful beaches and seaside town feel.

hubble lighthouse york maine

Nubble Lighthouse in York, Maine.

Benjamin F Sullivan/Shutterstock


Population: 12,529

Founded in 1642, York is one of Maine’s oldest towns and is teeming with history. In the summer, there’s plenty to do to occupy your time, from visiting one of the small town’s four beaches or stopping by the Goldenrod for some saltwater taffy.

In the winter, York comes alive for the holidays with a light display at Nubble Lighthouse.

Lenox, Massachusetts, is located in the region known as the Berkshires.

lenox massachusetts

Lenox, Massachusetts.

Richard Cavalleri/Shutterstock


Population: 5,025

The town’s quaint downtown area has restaurants, shopping, and a lot of historic architecture. If you’re looking for something a little more lively to do, the local Tanglewood venue offers concerts and other events while parks and trails give you the opportunity to get outside and take in the natural beauty of the Berkshire mountains.

Oak Bluffs, Massachusetts, is a small town located on the island of Martha’s Vineyard.

oak bluffs marthas vineyard

Oak Bluffs, Massachusetts.

Megan.10/Shutterstock


Population: 4,678

The island town offers everything from sandy beaches to kayaking, paddle boarding, shopping, dining, and more. The town is also home to what are known as the “gingerbread cottages,” a collection of colorful 19th-century cottages at Oak Bluffs Campground that are actually a National Landmark.

Jamestown, Rhode Island, is known for its quaint downtown area and close proximity to Newport.

jamestown rhode island harbor

Jamestown, Rhode Island.

James Kirkikis/Shutterstock


Population: 5,405

Located on Conanicut Island, Jamestown is one of Rhode Island’s most historic towns. The town is known for its historic homes, many of which date back to the colonial era.

The Newport Pell Bridge connects Jamestown and the nearby city of Newport, Rhode Island. Each summer, Newport comes alive with tourists from all over the world who come to eat in its restaurants, stroll through its cobblestone streets, and pop into one of the many retail stores the town has to offer. 

Around the holidays, you can find festive light displays and even tour one of Newport’s historic mansions

Stowe, Vermont, is known as the “Ski Capital of the East.”

stowe vermont

Stowe, Vermont.


Shutterstock/DonLand



Population: 201

Stowe, Vermont, is a popular tourist destination for skiing, though the town has more to offer as well. There’s shopping, restaurants, and some of the most beautiful fall foliage you’ll find in New England.

Woodstock, Vermont

woodstock in vermont

The Woodstock Inn in Woodstock, Vermont.

James Kirkikis/Shutterstock


Population: 2,937

Woodstock, Vermont, is widely regarded as one of the most quintessentially New England towns in the country. Gorgeous in both the fall and the dead of winter, Woodstock has a number of attractions and activities the whole family will love.

If you’re planning to stay in town over the holidays or the winter season, try to book a room at the cozy and festive Woodstock Inn. Each guest suite has its own fireplace perfect for cuddling up with a cup of hot cocoa and a copy of “‘Twas The Night Before Christmas.”



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