Small Towns In New England

The 7 Most Beautiful Small Towns In New England

Thanks to its extremely diverse population, landscape and culture, the United States is home to an abundance of quirky small towns. We took the time to research the ones that best fit the bill for a staycation this year. These small towns in New England tick all the boxes!

Beautiful Small Towns In New England

1. Stockbridge, Massachusetts

Stockbridge looks like something out of a Norman Rockwell painting, and that’s because it is! This cosy New England town was made famous by his portrayal of the city during Christmas. Stockbridge is the ideal New England small-town.

Its charming square, constant community events, historic inns, local eateries and preserved homes make it top the list for the best small towns in New England.

Image result for stockbridge ma

2. Woodstock, Vermont

Woodstock has all the fixin’s of a charming small town. New England character, prideful locals, surrounding scenery and unbelievably charming old town. In Woodstock, you can enjoy delicious farm to table meals, endless scenic trails and then experience its rural heritage without ever getting on a highway.

3. Sugar Hill, New Hampshire

Few things wow like Sugar Hill’s sweeping views of New Hampshire. This tiny New Hamshire town is known for its stunning fall foliage and annual Lupine festival in addition to its gorgeous natural beauty. Take in the meadows in the spring or fiery trees in the fall; Sugar Hill is lovely year-round.

Virtual Visit | Sugar Hill, New Hampshire: The Granite State's ...

4. Mystic, Connecticut

This seaside village is every bit as charming as you’d expect with a name like ‘Mystic’. Tirelessly devoted to all things nautical, this cosy Connecticut town is unbelievably cute. Plenty of local festivals, markets and community get-togethers bring the place to life. Additionally, the Historic Downtown features plenty of great options for local dining, nightlife and shopping.

5. Stowe, Vermont

Famous as a family fun summer destination or winter hotspot for skiers, Stowe is one of America’s best small-towns. Get your fill of local fare while taking in the surrounding natural beauty with plenty of outdoor activities. Whether you want to bike, fish, or hike, there’s something for everyone.

Vermont chapel | Stowe vermont, Fall foliage vermont, Travel images

6. Nantucket, Massachusetts

This former whaling village sings of the old days with its crooked cobblestone streets and sleepy harbours. While widely known as a tourist destination, Cape Cod has done an excellent job of ensuring that it doesn’t turn into a tacky vacay-town. Eat your heart out with their world-famous seafood and then take in the golden beaches.

small towns New England

7. Great Barrington, Massachusetts

Berkshire County’s Great Barrington is known for being one of the country’s most charming small towns. An oasis for nature lovers and art aficionados, there’s something for everyone. Sip on fresh spiced cider from a local farmer, catch a show at Mahaiwe, explore the Berkshires or grab a bite and drink at any of the charming small towns gastro gems.

small towns New England

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Sarah Clayton-Lea
Sarah Clayton-Lea

Co-founder of Big 7 Travel, Sarah created the company through her passion for championing the world's best food and travel experiences. Before her career in digital media, where she previously held roles such as Editor of Food&Wine Ireland, Sarah worked in the hospitality industry in Dublin and New York.

Contact [email protected]

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How can you talk about Sugar Hill and not mention the Pancakes from Pollys Pancake Parlor.