Courtesy of Jackson Hole Chamber of Commerce

Play it cool in these scenic small towns that know just how to embrace winter.

Jackson, WY

3 of 14

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.

Get more holiday travel inspiration.

America's Prettiest Winter Towns

Jackson, WY

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.

Get more holiday travel inspiration.

Courtesy of Jackson Hole Chamber of Commerce

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.

Related: America's Best Cities for Winter Travel

“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?

Related: America's Favorite Mountain 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.

Related: America's Best Mountain Resorts

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

Get more holiday travel inspiration.

Promoted Stories
Explore More
More from T+L