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It was 12 degrees and gusty when I started up the snowshoe trail that leads to the top of Mount Tom, the forested knob that looms just above Woodstock, Vermont. I moved fast, stabbing the frozen snow with my ski poles, rounding switchbacks, listening to rattling beech leaves, pale as parchment, that somehow refused to drop last fall. I seemed to be the only one on the Faulkner Trail that morning—no big surprise, given the weather. But I didn’t mind; I was generating my own warmth.

Some of that warmth, I should confess, may have been helped along by the breakfast I’d had earlier at the Woodstocker Inn, a goldfinch-yellow Cape set alongside the Ottauquechee River a few blocks from the village center. I’d turned down the signature sausage-heavy English breakfast offered by Dora Foschi and David Livesley, the inn’s cheery British expat owners, and ordered instead the noble steel-cut oatmeal—which David had presented with a little pitcher of Chivas Regal whisky on the side. Then he had stepped back and looked at me with an expectant smile. I hadn’t wanted to disappoint.

About a mile and a half up, I arrived at the South Peak overlook. From this vantage point, all of Woodstock was at my feet, laid out like a hobbyist’s model village: stately brick houses and white clapboard inns; pines like bottlebrushes near the elliptical snow-covered town green; and spanning a ribbon of dark river, the long, peaked roof of a covered bridge. I was just 2½ hours from Boston, but a world away.

The view hasn’t changed all that much from more than a century ago. When innkeepers began hosting winter carnivals here in the early 1900’s, it was a novel idea—that winter might be something to be embraced, rather than simply endured. Promoters of Vermont’s fledgling off-season tourism touted not just the beauty of the countryside but also its power, which—if you really got outside and experienced it—“renews our spunk,” as one writer put it at the time. City dwellers crowded onto Woodstock-bound trains for rollicking weekends of tobogganing down 1,000-foot snow chutes, ice skating on a rink at the village green (waltz and polka music provided by windup Victrolas), and ski jumping off high ramps.

Downhill skiing became the main draw beginning in 1934, when locals figured out a way to rig up the country’s first rope tow. Powered by a Ford Model T engine, it dragged skiers up a sloped sheep pasture at Gilbert’s Hill on a farm just a mile outside of town. More tows sprang up on nearby hills, and skiers descended on Woodstock. Eventually, big mountain resorts (Killington, Pico, and Okemo are less than 26 miles away) eclipsed all of the area’s original pocket-size hills but one: Suicide Six, where I’d skied the day before in bright sun and polar cold and had the baby-blue chairlift and the steep, groomed front face nearly to myself.

Woodstock might have faded as a tourist destination if not for the largesse of Laurance Rockefeller, who adopted the town after marrying Mary Billings French, granddaughter of railroad magnate and summer resident Frederick Billings. Besides saving little Suicide Six from its likely demise, Rockefeller bought and restored the landmark Woodstock Inn & Resort, expanded the country club and Nordic ski center (now with 18½ miles of trails), donated the Billings mansion and farm to the National Park Service, and even funded the burying of power lines in order to preserve the downtown’s 19th-century look.

But Woodstock is not frozen in time. In the past five years, there have been a series of openings and upgrades, most with a decidedly contemporary twist. The Woodstock Inn & Resort, after renovating all 142 rooms, unveiled a $10 million spa with 10 treatment rooms and a vaulted-ceiling Great Room filled with natural light. Just off the village green, the Blue Horse Inn opened in an 1831 brick Federal Greek Revival house with 10 guest rooms done in serene neutrals. Room No. 7, though, is a showstopping departure, with chic black-and-white toile wallpaper and crimson lamps.

Woodstock’s newest property, the 506 On The River Inn, debuted in February. Owner Aaren Macksoud grew up in town (his father runs a maple syrup operation on a nearby farm) and married into a hotelier family that also operates properties in Zanzibar, Nairobi, and Berlin. Throughout the 28-room, two-story hotel, spare cream and white interiors are warmed with vintage leather chesterfield sofas and quirky antiques: guests check in at an old drafting table and sip drinks at a massive bar that was salvaged from a monastery.

Some new construction was unplanned. Two iconic covered bridges near Woodstock, one in Taftsville and one in Quechee, were heavily damaged during Tropical Storm Irene in 2011. Both have since reopened. Also in Quechee, renowned glassmaker and restaurateur Simon Pearce had to rebuild his basement glassblowing studio after it was flooded in the storm. (One upside: the new space has a larger area for visitors to watch the glassmakers at work.) Pearce’s consistently excellent restaurant showcases both local producers, including vodka from Quechee’s own Vermont Spirits, and the family’s Celtic roots. The coarse Ballymaloe brown bread the kitchen serves is Simon’s mother’s recipe.

Worthy Kitchen, a gastropub that gained an instant following when it opened in 2013 in Woodstock’s east end, focuses on craft beers, many Vermont-brewed, and comfort food with a conscience: steak frites done with grass-fed beef; maple-bacon chicken wings from free-range birds. If you want to go hyperlocal, head to Cloudland Farm, a working farm four miles up a dirt road that serves BYOB dinners twice a week using its own pasture-raised beef, pork, and chicken in a beamed dining hall built from pine harvested from the property.

The cold wind finally drove me back down Mount Tom. In town, I warmed up with a maple latte and a cranberry scone at the snug Mon Vert Café, then browsed a few shops: the 128-year-old F.H. Gillingham & Sons general store, selling everything from guitars to goat’s-milk soap; Elevation, which carries Vermont-made Ibex merino-wool outdoor clothing; and Collective, an artisan-owned craft gallery where Rachel Kahn’s intricate hand-knit hats caught my eye.

Then, I was off to Twin Farms, 10 miles to the north. At the all-inclusive hideaway on the hilly former estate of writer Sinclair Lewis, guests play hard by day (skating, sledding, snowshoeing, downhill and cross-country skiing—all equipment provided), then recover in luxurious “cottages,” where no request made to the crack staff is too small. My home for the night was the Studio, a contemporary-art-themed stone cottage filled with museum-worthy pieces by Stella, Hockney, Lichtenstein, and others. I had an hour or so of daylight left, so I bundled up again and took off on the cross-country ski trails that loop around the wooded 300-acre property, past other cottages and the private five-trail Alpine ski hill.

Dinner in the main house was a parade of artfully composed dishes: potato confit and boar canapés; mushroom soup with truffle foam; short ribs with golden beets, salsify, and sweet-potato purée—each paired with wines from the 26,000-bottle cellar.

After dinner, I walked back to my cottage under a three-quarter moon. The snow squeaked beneath my boots. Once inside, I noticed that the living room fireplace had been neatly prepped with kindling and logs. I lit the fire with a single match. Then I flopped down on the sofa, full, tired, happy—spunk thoroughly renewed.

Meg Lukens Noonan lives in New Hampshire and is the author of The Coat Route: Craft, Luxury, & Obsession on the Trail of a $50,000 Coat (Spiegel & Grau).