New England

15 Prettiest Winter Villages in New England

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

By Necee Regis

Feb 08 2022

wethersfield ct george savic

Wethersfield, Connecticut

Photo Credit : George Savic
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
Lenox, Massachusetts winter
Lenox, Massachusetts | 15 Prettiest Winter Villages in New England
Photo Credit : Kevin Sprague

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, Vermont winter
Woodstock, Vermont | 15 Prettiest Winter Villages in New England
Photo Credit : 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. woodstockvt.comSee 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
Photo Credit : Aimee Seavey

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. stockbridgechamber.orgSee More: The Red Lion Inn in Stockbridge, MA | A Historic New England Inn
Grafton, Vermont
Grafton, Vermont | 15 Prettiest Winter Villages in New England
Photo Credit : Aimee Tucker

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. graftonvermont.orgSee 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 winter
Shelburne Falls, MA | 15 Prettiest Winter Villages in New England
Photo Credit : Phil Billitz - Creative Commons License: Attribution-NonCommercial-NoDerivs CC BY-NC-ND

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 Galleryshelburnefalls.comSee More: Guide to Shelburne, MA | Eat, Play, Stay
Wickford, Rhode Island
Wickford, Rhode Island | 15 Prettiest Winter Villages in New England
Photo Credit : Melissa Devine

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 mt hope Suzanne Munroe
Mt. Hope Farm in Bristol, Rhode Island. | 15 Prettiest Winter Villages in New England
Photo Credit : Suzanne Munroe

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
Kent, Connecticut winter
Kent, Connecticut | 15 Prettiest Winter Villages in New England
Photo Credit : Lyn Stirnweiss

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
Middlebury, Vermont
Middlebury, Vermont | 15 Prettiest Winter Villages in New England
Photo Credit : Teena Betourney

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

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
marlow nh stephanie tickner
Marlow, New Hampshire | 15 Prettiest Winter Villages in New England
Photo Credit : Stephanie Tickner

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.
Top 5 New England Winter Getaways
North Conway Village, New Hampshire | 15 Prettiest Winter Villages in New England
Photo Credit : Dick Pollock

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 Museumnorthconwayvillage.netSee More: Guide to North Conway, NH | Eat, Play, Stay
Wiscasset Village winter
Wiscasset Village, Maine | 15 Prettiest Winter Villages in New England
Photo Credit : Pat Cloutier

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. Visit Sarah’s Cafe for casual dining with river views, or check out the cozy Little Village Bistro for elegant, Italian-inspired cuisine. 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