Play it cool in these scenic small towns that know just how to embrace winter.
America's Prettiest Winter Towns
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.
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?
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“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.
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Ready to dive into an authentic winter experience? Follow our lead to America’s prettiest winter towns.