Winter Weekend in Vermont’s Deerfield Valley

There is an “ahhh” moment that people talk about when they cross the border into Vermont. The billboards disappear (they are not legal in the state), weathered barns shoulder the winter snowpack, dirt roads meander up the hillsides into hidden hollows. It doesn’t take long for the gentleness of the rural landscape to sink into your soul. Just a 25-mile drive from the Massachusetts border on I-91, the Deerfield Valley is classic Vermont. It’s also a place that has seen many upgrades in the past few years.

In 2019, Vail Resorts bought the ski resort Mount Snow and made it part of its Epic Pass offerings. Then Covid hit, and many establishments closed up shop. But since then, the Deerfield Valley has had a resurgence: Dozens of new restaurants, hotels, and breweries have blossomed up and down Route 100 in the eight or so miles that link the historic town of Wilmington with West Dover and Mount Snow.

Thankfully, careful stewardship has ensured that many of the new establishments have built on the valley’s heritage. Barnboard and white clapboard, family-owned restaurants, and proud innkeepers still prevail. And thanks to a legacy of skiing, you’ll also find a touch of the Alps on the menus and in the decor.

Where to Eat & Drink in Vermont’s Deerfield Valley

1. Go for gourmet fondue … in a gondola. If your vision of a perfect après-ski moment is sitting on a leather banquette in a refurbished private gondola car and noshing on fondue and venison meatballs while perusing an award-winning wine list, the Hermitage Inn has you covered. Work up an appetite by cross-country skiing on one of the trails that wind through the inn’s 112 acres, and then retire to one of the elegant historic rooms, completely renovated in 2021. thehermitageinnvermont.com

2. Dine Alpine-style. Sheepskin throws and candles lend a cozy ambience to the Alpenglow Bistro, where the menu starts with Bavarian pretzels and oysters before letting you move on to such Alpine favorites as savory crepes, fondues, and bratwurst. alpenglowbistrovt.com

3. Go beer-tasting. Home to one of the biggest and oldest beer festivals (held in both fall and winter at Mount Snow), the Deerfield Valley has experienced an explosion of microbreweries. Wilmington’s Valley Craft Ales opened in 2022 and now has a brewpub in the Old Red Mill Inn, with reasonably priced rooms upstairs for those who don’t want to drive. At Snow Republic Brewery, located in the largest log cabin in Vermont, order a Hop Avalanche and let the kids enjoy the shufflepuck and other games. Set atop Hogback Mountain in nearby Marlboro, Beer Nakednot only boasts some of the best views in the state but also serves tasty wood-fired pizzas from Pizzapalooza (try the Honey Pear Pie with gorgonzola and maple bacon). valleybeer.io; snowrepublicbrewery.com; beernakedbrewery.com

4. Visit one of Vermont’s most treasured diners. Betsey’s Dot’s of Dover has been one of Vermont’s best-loved places for eggs and pancakes for nearly 40 years—so much so that the town helped rebuild the place after it burned in a fire in 2019. dotsofdover.com

5. Fill up on local treats: cakes, breads, and coffee. The Deerfield Valley has no shortage of great bakeries. Home bakers Carolyn Weston and Andrew Allen opened Starfire Bakery in 2022 with menu items such as a pistachio-orange-cardamom cake. Just down Main Street in Wilmington, get a cup of locally roasted, sustainably sourced coffee at 1A Coffee Roasters; owners Brian and Chrystal Holt moved to Wilmington from Helsinki, Finland, where Brian worked at the U.S. embassy, and opened the roastery in 2018. And if you like crusty Italian breads and fresh challah, go to Sticky Fingers Bakery in West Dover. starfirebakery.com; 1acoffee.com; stickyfingersvermontbakery.com

6. Pay homage to an Olympic great. In 1979, Mount Snow ski instructors Terry and Cathy Clark opened a casual seasonal eatery, TC’s, in West Dover, then made it year-round in 1983. Their daughter, Kelly Clark, went on to become one of the most decorated snowboarders in history, earning three Olympic medals. TC’s tells her story in memorabilia and is now run by Kelly’s brother, Tim Clark, and his wife, Becky, who also run the more upscale restaurant Two Tannery Road. tcsrestaurantvt.com

Where to Stay in Vermont’s Deerfield Valley

7. Check into a classic Vermont hotel. The Vermont House is a four-column 1850s white Colonial in the heart of Wilmington that was recently renovated as a boutique hotel. Rooms are often under $200 a night. thevermonthouse.net

8. Bed down like a baron. Built in 1915 as the summer residence for a lumber baron, the White House Inn sits high on a hill with a view of the valley, like a grand dame surveying her surroundings. The inn’s restaurant, Clara’s Cucina Italiana, serves homemade pasta and Northern Italian specialties. whitehouseinnvt.com

Things to Do in Vermont’s Deerfield Valley

9. Skate by an outdoor fire. For a true Vermont-y moment, skate under the lights at the pond at West Dover’s Farm Road Estate, sip cocoa and roast a marshmallow at the outdoor firepits, or head into the inn’s Sawmill Bar & Table for house-made tortellini. Farm Road, renovated by new owners in 2020–2021, has rooms and cottages you can stay in as well. farmroadestate.com

10. Explore Mount Snow. Now owned by Vail Resorts and part of the Epic Pass program, Mount Snow has more than 600 skiable acres and a vertical drop of 1,700 feet. The resort hosts popular annual events such as the Cloud Nine nuptials (you can renew your vows atop the mountain), beer festivals, and the Duct Tape Derby. mountsnow.com

11. Watch the pros catch big air—or try it yourself. Some of the best freestyle skiers in the world have come out of Mount Snow’s terrain parks, and many still come back to train. You might catch a glimpse of World Cup winner Mac Forehand launching 80 feet in the air, or see Olympian Caroline Claire doing backflips. But it’s not all big jumps and rails: Mount Snow’s 100-acre Carinthia Parks section has a series of 10 progression terrain parks aimed at every skill level of skier or rider, from novice toddlers to pros. mountsnow.com

12. Make a day of it with the kids. There aren’t many places in Vermont where you can go snow tubing. Mount Snow is one of them, with eight lanes for you to rocket down and a dedicated magic-carpet lift to ferry you back up. After, head to the Last Chair Bar & Grill—set in a converted red barn in West Dover—to refuel with locally brewed drafts and a full après-ski-style menu while the kids play air hockey, shufflepuck, or Guitar Hero in their own arcade area. mountsnow.com; lastchairvt.com

13. Go on a snowmobile adventure. One of Vermont’s biggest expanses of undeveloped land sits just west of the Deerfield Valley. The local snowmobile clubs maintain trails in the Green Mountain National Forest, and Snowmobile Vermont offers two-hour guided tours out of its base in Woodford. snowmobilevermont.com/mount-snow

14. Ski backcountry glades. Put on some touring skis with climbing skins and explore four gladed backcountry ski zones in the 1,400-acre Dover Town Forest, part of the Southern Vermont Trails Association, or the four smaller zones in the Horace Hill trail network. The routes (including the uphill skin tracks) are flagged but ungroomed, so skiers should travel in groups, be prepared, and carry maps, GPS, and basic safety gear. sovta.org

15. Snowshoe or cross-country ski from mountain to town. Depending on snow conditions, use snowshoes, alpine touring gear, or cross-country skis to explore the Crosstown and Valley Trails, a network of groomed, flat trails between Mount Snow and the towns of Dover and Wilmington. doververmont.com/community/page/crosstown-trails

16. Conquer a section of the Catamount Trail. One of the most beautiful sections of the Catamount, the state-long backcountry ski-touring trail, Section 3 runs 7.4 miles from Route 9 in Searsburg to the Somerset Reservoir, traversing a gorgeous, remote area west of Mount Snow. It’s generally flat with a few steep uphills and some small stream crossings. catamounttrail.org/ski-the-trail

17. Catch a live music show with a comedic twist. Comedian/musician/entertainer Bruce Jacques has spent many of his winter weekends for the past 30 years in the Deerfield Valley doing classic rock covers (and hilarious impersonations), with his shows often ending with patrons dancing on the tables. Catch the local legend himself at Mount Snow’s Cuzzins Bar & Grill in the base lodge on many Saturday nights and at other local music venues. brucejacques.com

18. Laugh at art. For humor with a bit of an acerbic (and often political) bite, stop by the Art of Humor Gallery in Wilmington, which features work by late gallery owner Skip Morrow. He started his cartoon career with the book I Hate Cats and published more than 20 other books, including I Still Hate Cats. skipmorrow.com

Where to Shop in Vermont’s Deerfield Valley

19. Bring home some local handcrafts. For 50 years, the Vermont Bowl Company in Wilmington has been producing hand-turned wooden bowls designed by local artisan John McLeod as well as cutting boards and other great gift items. Also in Wilmington, Far Beyond Woodworking’s Mark Sprague creates gorgeous custom furniture, much of it handmade and inlaid. vermontbowl.com; farbeyondwoodworking.com

20. Treat yourself to a good read. A classic independent bookstore for 35 years, Bartleby’s Books in the heart of Wilmington channels rustic Vermont as it offers the perfect book to curl up with by a fire, including classics by local authors such as John Irving’s The Last Chairlift or a mystery by Archer Mayor.myvermontbookstore.com