Though beautiful year-round, some towns become even more charming once the snow flies. Here we present the prettiest winter villages in New England.

Necee Regis ~ New England Travel News

Litchfield, CT

Settled in 1721, the Colonial-era town nestles in an Arcadian landscape. A former 19th-century artisan hotspot, visitors today enjoy shopping for antiques, art, and gifts along the village green. Or visit the nature museum and hiking trails at the White Memorial Conservation

Lenox, Massachusetts winter

Lenox, Massachusetts | 15 Prettiest Winter Villages in New England Kevin Sprague

Lenox, MA

Set in the bucolic Berkshire hills, this walking village is renowned for its architecturally diverse churches, farm-to-table restaurants, and high-end boutiques selling art, antiques, clothing, jewelry, and crafts. Open year-round, Ventfort Hall offers tours of its Gilded Age splendors.

Woodstock, Vermont winter

Woodstock, Vermont | 15 Prettiest Winter Villages in New England Samuel M Purvis IV

Woodstock, VT

In this rural New England town, population 900, stately 18th- and 19th-century homes and public buildings rim the village green. Cross the Ottauquechee River on a covered bridge, and visit galleries, restaurants, and shops along Elm and Central streets. Don’t miss F. H. Gillingham & Sons, a vintage general store.

See More: Wassail Weekend | Holiday Fun in Woodstock, Vermont

stockbridge ma | 15 Prettiest Winter Villages in New England

Stockbridge, Massachusetts celebrating its annual Rockwell Christmas weekend. | 15 Prettiest Winter Villages in New England

Stockbridge, MA

In pastoral western Massachusetts, the 18th- and 19th-century buildings along Main Street look much the same as when Norman Rockwell painted his iconic image in the 1950’s. The Red Lion Inn, circa 1773, is one of the nation’s oldest continuously operating historic inns.

See More: The Red Lion Inn in Stockbridge, MA | A Historic New England Inn

Grafton, Vermont

Grafton, Vermont | 15 Prettiest Winter Villages in New England Aimee Tucker


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