Favorite Things to Do in Woodstock, Vermont

Please note that many establishments throughout New England have modified their hours and/or operations in response to COVID-19. Always check for the latest information before making travel plans.

To complement season 1, episode 11 of the public television series Weekends with Yankee, we asked Amy Traverso, the show’s cohost and Yankee’s senior food editor, to share a few of her favorite things to do in Woodstock, Vermont.

Amy Traverso’s Favorite Things to Do in Woodstock, Vermont

Woodstock, Vermont, is one of my favorite places in New England. I love the village, with its hiking trails and restaurants and 1886 general store. I love that hiking, skiing, and swimming are all within easy reach from town. And I love that in every season, there’s something to do and explore. Here’s a tour of some of Woodstock’s best offerings to help you plan your next visit.

A cozy corner of the Woodstock Inn & Resort.

Tara Donne

Hotels in Woodstock, Vermont

Like many of Vermont’s other top tourist destinations, Woodstock has an abundance of inns and bed-and-breakfasts. The Woodstock Inn & Resort, built on the site of a 1793 tavern, is the local grande dame, occupying a prime spot on the town green. Recently remodeled, the inn has achieved a style that feels fresh and uniquely Vermont, with a roaring central fireplace (in cool-weather months) and an airy spa with its own courtyard hot tub (book a treatment and enjoy the facilities all day). Just down the road, the fitness center is perfect for an après-ski or après-golf soak. (Tip: Book a room during the annual post-Thanksgiving sale and enjoy a five-star inn at three-star prices.)

Newer on the scene, the family-friendly 506 On the River Inn sits about two miles out of town on the banks of the Ottauquechee River and offers cool country-industrial decor, spacious rooms and suites, an indoor pool and spa, free breakfast, and game rooms for rainy days.

Pint-size skiers at Suicide Six.

Tara Donne

Outdoor Things to Do in Woodstock, Vermont

Hiking up Mount Tom takes just 30 minutes from town (the trail begins on Mountain Avenue, behind the covered bridge), and the summit provides a stunning view of the entire village. In winter, you can strap on your snowshoes or cross-country skis to make the journey. But beyond that one hike, you’ll find a network of interconnected trails throughout and around the town that pass through a national park and along meadows and ponds.

The Suicide Six ski area, one town over in South Pomfret, is one of the best small ski mountains in New England, with trails for skiers at every level and a cozy vibe. If cross-country skiing is more your speed, the Tubbs Snowshoes and Nordic Adventure Center, part of the Woodstock Inn’s property but open to the public, offers nearly 20 miles of groomed trails.

In summer, go for a swim at Silver Lake in nearby Barnard, then grab some ice cream or a fresh sandwich at the Barnard General Store.

A window filled with snow-day reading inspiration at the Yankee Bookshop.

Tara Donne

Shopping & Things to Do in Woodstock, Vermont

At Farmhouse Pottery, they’ve been designing and crafting pottery, housewares, and accessories in an ever-expanding product line for more than a decade. Bookworms will find a well-curated selection at the Yankee Bookshop. The Woodstock Farmers Market is the kind of locally inspired small grocery that every town should have, stocked with fresh produce, staples, and Vermont-made cheeses, chocolates, jams, breads, and more.

I could spend an entire day in F.H. Gillingham & Sons, a sprawling general store that first opened its doors in 1886. It is still family-owned, now run by the founder’s great-grandsons, and offers a bit of everything, from gardening essentials to fishing tackle to toys and gluten-free crackers.

Billings Farm and Museum offers a taste of traditional New England farm life c. 1890, from butter-making and sheep-shearing demonstrations (the museum’s main season runs May to October, but it opens for special weekend and holiday events, such as sleigh rides, in the winter).

The mansion at the Marsh-Billings-Rockefeller National Historical Park (named after the families who have successively owned the property) offers a stunning example of Queen Anne–style architecture (complete with Tiffany stained glass windows) and gardens designed by some of the most renowned landscape architects of their time. This seasonal attraction is open from late May through October.

Middle Bridge, a single-lane span over the Ottauquechee River in the heart of town, is one of the most photographed covered bridges in New England.

Watch master glass artisans at work at the Simon Pearce flagship store in nearby Quechee, shop for tableware and home decor, then have dinner at the award-winning restaurant the Mill at Simon Pearce.

Mountain Creamery in Woodstock Vermont VerMonte Cristo

The signature VerMonte Cristo at Mountain Creamery in Woodstock, Vermont.

Clare Barboza

Restaurants in Woodstock, Vermont

Cloudland Farm is a true farm-to-table experience, located in a post-and-beam structure on the Emmons family farm in Pomfret, a short, scenic drive from town. Here, you can enjoy fresh meats and vegetables from this and other nearby farms prepared with French and American accents (choose from two- or three-course prix fixe options). Just outside town, Worthy Kitchen offers craft beer and terrific comfort fare (burgers, poutine, fried chicken, local cheeses).

And right in the heart of Woodstock, Mountain Creamery is a great place to grab a VerMonte Cristo sandwich (ham, turkey, and Swiss between French toast slices, served with a side of maple syrup) and a slice of mile-high apple pie. Finally, for more upscale options, try the Lincoln Inn & Restaurant, where chef Jevgenija Saromova takes years of restaurant training in Italy, England, and France and applies them to the seasonal flavors of Vermont.

Have you ever visited Woodstock, Vermont? Tell us some of your favorite things to see and do in Woodstock!

This post was first published in 2017 and has been updated.

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