America's Prettiest Winter Towns

You don’t need to find a beach to beat the winter blues. There’s an invigorating, rosy-cheek feeling that comes from a day out among fresh air and snow—followed by something hot to drink.

That’s the promise of America’s prettiest winter towns, where you can wander among beautiful historic streets with eclectic businesses and scenic surroundings—whether laced with cross-country trails or vineyards whose tasting rooms beckon with fireplaces. Even when snowfall is sporadic, towns like Jackson, WY, or Charlottesville, VA, have undeniable, picturesque appeal. There’s always something to do, and the passion their residents pour into cold-weather pursuits is contagious.

“When you walk into a great winter town, you immediately feel like you’re in its embrace,” says David K. Gibson, editor in chief for luxury lifestyle magazine Snow. “The joy comes in being able to walk from your hotel to the coffee shop, where you can talk to your barista, and she tells you where to go for dinner, and then your waiter at dinner tells you where to go skiing,” he says.

Consider it done in the friendly, artsy town of Red River among the Sangre de Cristo Mountains of New Mexico. Visitors, many from Texas, hit the slopes and then go for après-ski drinks along the town’s main drag. And is it any surprise that New England, the birthplace of the American ski industry, has its share of pretty winter towns?

“We have mountains, we have inns, we have a tradition of people coming here that goes way back,” says Mel Allen, editor of Yankee magazine. “Winter tourism is not a new thing for New England—many of the inns have been here a long time, and they know how to make people feel welcome.”

Grafton, VT, owes the upkeep of its clapboard buildings and Normal Rockwell–esque taverns and art galleries to the Windham Foundation, charged with promoting the state’s rural communities. The town—population 600—is far from Disneyfied, despite the historical aura and pastoral views at every turn.

Ready to dive into an authentic winter experience? Follow our lead to America’s prettiest winter towns.

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The Blue Ridge Parkway passes by this century-old mountain town, whose Main Street has shops for antiques, crafts, even dulcimers. Streams trickling through quiet forests banked with snow inspire exploring and reflection. After a day out, tuck into ham biscuits at Knight's on Main or go for more sophisticated southern fare like smoked North Carolina trout and sweet potato soup.

Winter Fun: Nearby ski areas—Appalachian Ski Mountain, Ski Beech, and Sugar Mountain—provide downhill action. And every year in late January, Winterfest takes over. During the Polar Plunge, costumed locals and visitors take an icy stride off a boat dock into frigid Chetola Lake.

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For all the tony chalets dotting its mountainsides, Jackson remains one of America’s most authentic western destinations. Mom-and-pop motels share the streets with exclusive furriers, and off-duty ranchers in boots still ask for a lady’s hand to dance at the Million Dollar Cowboy Bar. The Grand Tetons loom overhead, and the nearby slopes of Jackson Hole deliver steep, powdery runs. A fence on Jackson’s northern edge denotes the boundary with Grand Teton National Park and the National Elk Refuge.

Winter Fun: Bears are hibernating, but snow at high elevations pushes many other animals into the valley during winter. Jackson Hole Wildlife Safaris leads tours in Grand Teton National Park, where you’ll likely see (and hear) wolves, coyotes, elk, bighorn sheep, mule deer, and moose.

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Visitors to Yellowstone and the epic ski mountain at Big Sky often fly into Bozeman and head onward. But it’s worth lingering in this eclectic community of artists, outdoorsmen, and college students. Lined with turn-of-the-century buildings that once outfitted miners and ranchers (indeed, some still do outfit the latter), Main Street now caters to locals with coffeehouses, galleries, sports bars, and shops for vintage clothes and handmade jewelry. When snowflakes fall on the red brick façades, everything is even more atmospheric.

Winter Fun: Make the day trip to test your mushing skills with Yellowstone Dog Sledding Adventures. The mountain scenery, fresh winter air, and pitter-patter of husky paws on snow distill Montana’s wilderness to its purest incarnation.

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Lowcountry cities like Charleston, SC, and Savannah, GA, hog the tourism spotlight, which might be fine with Charlottesville residents—happy to keep their artsy college town to themselves. Things do pick up in the summer and fall, thanks to the burgeoning vineyard scene. But winter has a special beauty, found while admiring Monticello and the University of Virginia covered in white, snowshoeing along the trails of the Blue Ridge Parkway, or sipping a glass of local Merlot in a restaurant along Charlottesville’s pedestrian-friendly Downtown Mall.

Winter Fun: Virginia is the country’s fifth largest wine producer, and you can tour vineyards along the Monticello Wine Trail. The tasting room at King Family Vineyards is particularly cozy, with a stone fireplace.

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In the foothills of the Green Mountains, Grafton owes the upkeep of its clapboard buildings and Norman Rockwell–esque stores, small galleries, and taverns to the Windham Foundation, charged with promoting Vermont’s rural communities. Despite the historical aura and pastoral views at every turn, Grafton (population: 600) is far from Disneyfied. Winter visitors come for Nordic skiing, ice skating, and snowshoeing in the state where the American ski industry was born—and for the cozy inns with comfort food that await at the day’s end.

Winter Fun: Grafton locals are often spotted with skis over their shoulders, heading into the woods. You can practice cross-country skiing on the corduroy-groomed runs at the Grafton Ponds Outdoor Center, where snowshoeing and snow tubing are also available.

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For all of the Rockies’ flashy resorts and rustic ranches, few places compare to the erstwhile mining town of Ouray when it comes to an authentic and adventurous winter vibe. Where else can you stroll streets with Victorian buildings, ogle ice climbers dangling from their pickaxes nearby, and then melt into the therapeutic warmth of a vapor cave discovered by miners searching for gold? While scaling enormous ice formations (or simply observing) may be the winter pastime of choice, there’s snowshoeing and skiing, too.

Winter Fun: Join the crowds at Ouray’s bridges to watch daredevil mountaineers swing their axes into the frozen faces at the Ouray Ice Park, then warm up with a dip in pools fed by natural springs at the Wiesbaden Hot Springs Spa, also the site of the vapor cave.

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Horse-drawn sleigh rides clomp through town, making forays into the pine-laden White Mountains surrounding Bethel. Roam around Bethel’s Main Street, and you’ll get your fill of everything cozy and inviting about winter in one of New England’s prettiest towns. Peer into the windows of inns housed in 19th-century buildings that glow with open hearth and candlelight. Just be prepared to be tempted off the snowy streets and indoors for a hearty meal of shepherd’s pie and Yankee pot roast.

Winter Fun: Five miles outside of Bethel, Mount Abram is the perfect beginner’s mountain for learning how to ski or snowboard, with a ski school for kids and just over 20 trails to explore (and not get lost on).

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Scandinavian roots mean Minnesotans know a thing or two about enjoying winter in all of its ice-cold, iced-down glory. Counterintuitively for the state, the southeastern town of Lanesboro is not a land of lakes but rather of river gorges and high limestone bluffs that makes for a winter wonderland of a different sort in the Root River Valley. Nordic skiers schuss out of town—past the Victorian façades in the center, where there’s neither a stoplight nor a franchise store—toward those haunting empty places that beckon.

Winter Fun: Skiers flock to the Root River Trail throughout winter, but on the first Saturday in February every year, it is lined with candles during the Whalan Candle Light Cross-Country Ski.

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If exploring one of the country’s most timeless villages—with a still-operating congregational church where George Washington and John Adams used to worship—sounds like your idea of wintertime fun, then Old Wethersfield is the place. Connecticut’s largest historic district and first permanent settlement counts 150-plus buildings that date from before 1850 (another 50 predate the Revolutionary War). Yet the town supports a vibrant community; neighbors still gather at their mailboxes to say hello and wave while walking their dogs.

Winter Fun: Bundle up for a leisurely stroll, then pop into the Silas W. Robbins House Bed and Breakfast. The immaculately restored property facing the town green dates back to 1873 and is decorated with period furniture.

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Forget visions of rainy Seattle. This town in eastern Washington gets its fair share of sunshine: more than 180 days per year contribute to the fine wines that hail from here. Those rays make this park-filled college town all the more attractive as an escape from the Northwest winter blahs. Walla Walla’s friendliness and beautiful Beaux-Arts and Victorian buildings—occupied by independent coffee shops, boutiques, and bistros—do wonders. The region’s 100-plus vineyards, and bars that pour their wines, will also do their part to lift your spirits.

Winter Fun: Perfect your spins or try your hand at broomball at the YWCA Ice Chalet Ice Skating Rink, an indoor rink playing retro disco and ’80s music. Bluewood Ski Resort is 52 miles away, and the hills of the nearby Umatilla National Forest offer cross-country and snowshoeing.

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With the Selkirk Mountains (alt. 8,000 feet) as their backdrop and Lake Pend Oreille for a centerpiece, Sandpoint’s roughly 7,500 residents are largely of the skiing, sailing, hiking, fishing, and paddleboarding variety. But the town also supports the arts; see what’s playing at the historic Spanish mission–style Panida Theater. Breweries, a vineyard, and a fiercely independent retail and dining scene are icing on the cake for locals—and travelers savvy enough to swing by. Sandpoint is only 75 miles from Spokane, across the Washington State border.

Winter Fun: Join Selkirk Powder for Sno-cat treks to Schweitzer Mountain’s wild west side, where you and a maximum of nine others can enjoy 4,000 acres of fresh tracks in terrain tracked by mountain lions and home to woodland caribou and grizzly bears.

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This town northeast of Taos in the Sangre de Cristo Mountains is where many Texan kids take their first turns before discovering the big resorts of Colorado and beyond. There’s just one funky road through Red River—shared by alpine-style restaurants and bars, draft beer, and Texas barbecue joints—and the earthy, artsy vibe gets balanced by lots of big hair and Texan twang. The mountain’s good range of predominantly intermediate ski terrain means you probably won’t be too tuckered out to join the roving après-ski party along the main drag.

Winter Fun: Go on a guided snowmobile tour with Bobcat Pass Wilderness Adventures and float atop the powder at 9,820 feet in the Kit Carlson National Forest, with miles of trails crossed by elk, mountain lions, and bobcats.

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