15 Prettiest Winter Villages in New England

New England is beautiful in any season, but here are the 15 villages that are even more charming with a little snow on the ground.

15 Prettiest Winter Villages in New England

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 Center. 

Lenox, MA

Set in the bucolic Berkshire hills, this walking village is renowned for it’s 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, 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

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, VT

This picture-perfect village, population 600, is known for its restored historic buildings that house art galleries, small museums, and shops selling artisan breads, preserves, maple products, and cheese. The Grafton Inn, circa 1801, offers a quintessential Green Mountain experience. 

See More: Grafton, Vermont | A Quiet and Cozy Winter Town

Wethersfield, CT

Step into the past in this charming village where 375 years of heritage is preserved and celebrated. In the Historic District, see more than 300 houses from pre-Revolutionary days through shortly after the Civil War. Tour artifact-filled museums, graceful churches, ancient burial grounds, and shops selling antiques, art, crafts, jewelry and one-of-a-kind treasures. Start your tour at the Wethersfield Museum.

Shelburne Falls, MA

Incorporated in 1775, the quaint and artsy village spans the mellow Deerfield River in the Pioneer Valley. The laid-back downtown is home to art galleries, studios, restaurants, and mom-and-pop shops. See work by 100+ artists, and a stunning river view, at Salmon Falls Gallery. 

See More: Guide to Shelburne, MA | Eat, Play, Stay

Wickford, RI

Salty breezes enliven this waterfront town that boasts architecturally intact churches and historic homes dating back to the 1700s. Over 50 indie shops sell gifts, jewelry, art, books and home goods. Take a self-guided walking tour of 20 noteworthy buildings. 

Bristol, RI

This archetypal New England port town has been a sailing and shipbuilding center for more than three centuries. In the well-preserved waterfront district, you’ll find boutique shops, restaurants, churches and slave-traders’ mansions. Boat enthusiasts enjoy the Herreshoff Marine Museum and America’s Cup Hall of Fame.

Kent, CT

In the rolling hills of western Connecticut, a stone’s throw from New York State, this small rural village is chock-a-block full with charming art galleries, shops, restaurants, and churches. For a true Americana experience, visit Eric Sloane Museum & Kent Iron Furnace. 

Middlebury, VT

Boutique shops, restaurants, and churches frame the historic downtown of this village, circa 1761, that nestles along Otter Creek in the pastoral hills of western Vermont. Home to Middlebury College, and the Henry Sheldon Museum of Vermont History. 

Rockport, ME

In this cultural town in mid-coast Maine, first settled in 1769, watch seagulls circle lobster boats in the harbor, and stroll the center to find farm-to-table, restaurants, galleries, a statue dedicated to Andre the Seal, and the perfect spot for a bundled up nature hike at Beech Hill Preserve.

Marlow, NH

It may be tiny, but this rural Yankee village, circa 1753, rates large on the picturesque scale. Around the town’s lily pond you’ll find the all-white Methodist Church, Odd Fellows Hall and Town Hall.

North Conway Village, NH

In the heart of New Hampshire’s White Mountains ski region, winsome storefronts along Main Street sell sporting goods and clothes, arts and crafts, locally-made gifts, chocolates and award-winning cupcakes. In the restored 1874 Boston & Maine railroad station, Conway Scenic Railway’s vintage trains evoke pleasures of travel in bygone days. Weather geeks enjoy the Mt. Washington Observatory Weather and Science Museum. 

See More: Guide to North Conway, NH | Eat, Play, Stay

Wiscasset, ME

Overlooking the Sheepscot River, this seaport town offers an abundance of architectural landmarks — many dating back to the 18th- and 19th-centuries. Antique shops, art galleries and museums line the historic center along Main Street.

Which New England winter villages would you add to the list?

This post was first published in 2015 and has been updated.

SEE MORE:
10 Best Winter Towns in New England

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