Fresh Snow, Oil Painting by Michael McGovern

Wassail Weekend kicks off winter excitement in Woodstock! This festive annual holiday event is held the second weekend in December and features three days of holiday shows, beautiful music, a parade of riders, horses and carriages, a historic house tour, a medieval banquet, a 19th Century Christmas celebration at Billings Farm & Museum and many more activities throughout the village. Voted one of Vermont's 10 best winter events.

Woodstock is an incredible winter wonderland from November to April. There are miles of trails for cross country skiing and snowshoeing, including trails in Vermont's only National Park. Our local Suicide Six ski area, located north of the village, offers excellent downhill skiing and snow boarding, and Woodstock is also located 20-25 minutes from four other terrific ski areas. Ice skating is available at the new Woodstock Union Arena, and on Silver Lake and many local ponds. And for the competitor(s) in the family, Woodstock hosts its own winter triathalon for all ages!

Middle Bridge, Oil Painting by Michael McGovern

Photo curtesy of Billings Farm & Museum

Come in from the cold and visit our wonderful, independently owned, unique shops and galleries, and savor a fabulous meal in one of our eateries. Woodstock boasts some of the best restaurants in Vermont! And for the romantic in all of us, a sleigh ride through the hills of Woodstock and South Woodstock or a full moon snowshoe hike is a great way to end a day.

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