Winter Weekend in Woodstock, Vermont

It’s a windy Saturday night in early February, and despite temperatures that plummet with every gust, there’s a lively après-ski crowd gathered around firepits outside Au Comptoir, a craft cocktail bar just behind Central Street in Woodstock, Vermont. Inside the white clapboard cottage (originally built as the personal garage of Laurance S. Rockefeller, whose largesse left a permanent stamp on this town), the decor is all reclaimed barn wood, antique brass, and marble. Owner Zoe Zilian was a cofounder of the artisan housewares brand Farmhouse Pottery, and there isn’t a sconce or bar stool or cocktail that isn’t expertly curated.

Au Comptoir encapsulates much of what is lovely and stylish about winter in Woodstock. The Danes may get through winter with their hygge—a quality that embraces coziness and small pleasures—but this Vermont village has its own brand of gentle comfort.

Consider Central Street: At the darkest time of the year, when most people have dutifully taken down their holiday decorations, this main commercial street still abounds with fairy lights sparkling in shop windows and sidewalk trees. Over on Elm Street, the Vermont Flannel Company specializes in the snuggliest of winter fabrics. And a few miles down the road in Quechee, you can dine in style in Simon Pearce Restaurant while gazing out at the dramatic falls that once powered a woolen mill here.

The Woodstock Inn & Resort commands a prime spot on the village green and boasts several satellite facilities, including the Saskadena Six Ski Area, a Nordic center, and a fitness center with an indoor pool, a sauna, a steam room, and a hot tub. A day on the slopes followed by a soak in the hot tub and a hot toddy at the inn’s Richardson’s Tavern is a good day.

On this visit, though, we’re lodging in a newer spot. The Vesper is a bed-and-breakfast run by Dana Hale, who updated an 1835 brick Greek Revival with colorful modern design featuring textiles and pottery from her partner Rafael’s native Guatemala. The couple have two young children, so it’s no surprise the B&B has a relaxed “we’re all family” vibe (so much so that the young couple we meet at breakfast become our companions for beers and rollicking conversation later that night).

The Vesper stands as a stylish, budget-friendly option right in the village and reminds us that while Woodstock has long had a reputation as a retreat for the Rockefeller set, it’s possible to enjoy a trip here without overspending. Consider this: A weekend day pass at Saskadena Six costs about half that of nearby Killington, and there’s something more intimate and welcoming about its smaller size and the crackling wood fires inside the lodge (and outside, as well).

Back in town, you’ll find shopping at many price points, from Farmhouse Pottery with its upscale home goods to the Yankee Bookshop, the perfect small-town bookstore. Founded in 1886, F.H. Gillingham & Sons reigns as the archetypal general store, complete with penny candy and Carhartt work wear. Meanwhile, the Norman Williams Public Library, housed in a stunning Romanesque building of pink sandstone and Barre granite, offers an eminently calming—and free—place to pass a snowy afternoon. (Note to parents: The children’s room downstairs is excellent and welcoming to visitors.)

Even if you’re not staying at the Woodstock Inn, you can still enjoy its athletic club via a $25 day pass that allows you to use all the exercise areas and the pool. The town’s three free trail networks are perfect for day hiking, snowshoeing, cross-country skiing, or fat-tire biking. Waiting for you afterward is perhaps a drink at Au Comptoir or a burger at Worthy Kitchen.

On our last day in town, we buy day passes at the Woodstock Nordic Center and head out on the trails that run around and through the golf course—the easiest route for our modest skills. A light coating of fresh flakes has blessed us with smooth tracks, and with a temperature of about 14 degrees, the snow makes that perfect squeaking sound as I glide alongside Kedron Brook.

Skate skiers zoom past me, glowing with rosy-cheeked good health, and—just as I do every time we visit Woodstock—I think about how much more outdoorsy and glowy I’d be if I lived here. I’m reminded of how many ways there are to truly enjoy the outdoors in winter. And I remember how to find warmth and comfort on the long, dark nights.

What to Do in Woodstock, Vermont

Dining in Woodstock, Vermont

Au Comptoir: There’s more to this bar’s popularity than just its sleek good looks. Juices are freshly squeezed, syrups and some bitters are made in-house, and many of the spirits hail from Vermont. aucomptoirvt.com

Ransom Tavern: Just down the road in South Woodstock’s Kedron Valley Inn, dig into Neapolitan-style pies from a Forza Forni gas-fired pizza oven. Imaginative combos include ingredients such as gorgonzola, maple syrup, and butternut squash. kedronvalleyinn.com

The Red Rooster: The Woodstock Inn’s signature restaurant offers seasonal fare that’s sourced locally and served with a Mediterranean accent. You can always count on the pork chop, the roast chicken, and the Vermont cheese plate. Don’t miss the Parker House rolls. woodstockinn.com

Simon Pearce Restaurant: For delicious food with a waterfall view, make a reservation: This upscale eatery adjoining the Simon Pearce glassblowing studio fills up fast, especially on the weekend. Save room for the triple chocolate layer cake. simonpearce.com

Worthy Kitchen: Craft beer lovers, rejoice: Worthy Kitchen has your Hill Farmstead, your Trillium, your Heady Topper. Use them to wash down smash burgers and crispy wings—and possibly a fresh doughnut or two. worthyvermont.com

Lodging in Woodstock, Vermont

The Vesper: The room names at this B&B pay homage to owner Dana Hale’s favorite musicians, and she brings her personal taste to the decor, too: part modern, part folk art, all colorful. Expect good coffee, a generous breakfast buffet, and general bonhomie. vesperwoodstock.com

Woodstock Inn & Resort: Classically elegant (“Vermont semiformal,” if you will), the inn offers a big crackling fire in the lobby, afternoon tea and cookies in the conservatory, a Vermont-meets-Scandinavia-style spa, and two top-notch restaurants. woodstockinn.com

Things to Do in Woodstock, Vermont

Artistree: This vibrant community arts space near Saskadena Six hosts live theater, touring musicians, jam sessions, and a gallery featuring the work of Vermont and New Hampshire artists. artistreevt.org

Billings Farm & Museum: Visit velvet-nosed Jersey cows in their milking parlor and tour an 1890 farm manager’s home at this beloved outdoor history museum. billingsfarm.org

Saskadena Six: With three lifts and 28 trails, the former Suicide Six ski area is perfect for novices but still fun for advanced skiers. saskadenasix.com

Woodstock Nordic Center: Buy or rent cross-country skiing equipment, sign up for lessons, or even have lunch at this well-appointed facility, which welcomes snowshoers and fat-tire bikers, too. woodstockinn.com