Woodstock's Gilbert's Hill, just north of the village on Route 12 is the site of the first ski tow in the United States. Alpine skiing as we know it today started with a rope two hooked to a model A engine which carried skiers up the hill to ski down. Several of our local residents were some of the first to try skiing with a "lift".

Now, we're located in the heart of Vermont alpine ski country (both big skiing and intimate, uncrowded skiing). For the latter, try Suicide Six, just three miles from the center of the village on the Stage Road. Weekend races and the local Ski Runners program provides skiing for residents while visitors can enjoy skiing at an affordable an unhurried pace.

Bear Creek Mountain offers exclusive skiing for those staying at their slope-side condominiums just down the road in Plymouth, Vermont.

Ascutney Resort offers a small resort complete with its own ski hill right on the hotel property in Brownsville, Vermont just 10 miles south of Woodstock near Windsor.

Larger resorts including Killington & Pico, 17 miles west of Woodstock and Okemo, 25 miles southwest of Woodstock, have ongoing activities and events for winter and summer. Within a forty mile radius, enjoy a full range of superb skiing in Vermont.

Woodstock's Ski Touring Center is one of the country's pre-eminent nordic centers which boasts 60 kilometers of groomed and tracked trails for classic nordic and ski-skating enthusiasts. The Center is located just a half a mile south on route 106 from the Village Green. You can purchase a trail pass, rent equipment or purchase the latest in nordic gear and then be on your way on to the trails on the golf course and Mt. Peg. Or take a short drive to the Prosper Road off Route 12 to enjoy the trails on Mt. Tom. The Ski Touring Center maintains these trails during the winter which are part of the Marsh Billings Rockefeller Historic National Park, providing endless opportunities to “get away from it all” while being right in the midst of the diverse community of Woodstock. Several olympic skiers on our US Nordic team have come from our village due to the strong coaching and intimate opportunities for young people to enjoy this sport.

In nearby Quechee, Wilderness Trails offers full nordic skiing on the Quechee Inn at Marshland Farm property on the River Road. Marty Banak provides all the equipement you need to enjoy these bucolic groomed trails near Dewey's Pond and the hills of Quechee Lakes.