Ice Skating is a natural fit for winter activities. Historically, Vermont's ponds and lakes have been swept of snow by townspeople eager for outdoor recreation during the long winter. Due to heavy snowfalls, skating on natural ice is relatively rare. Woodstock's low altitude (500 feet above sea level) and flat Village Green has often flooded and provided the center of the village a bucolic place to skate. The local fire departments have sometimes flooded the Green to provide a chance for skating parties during the winter months.

Today, the community rallied to raise funds to build the Union Arena at the Woodstock Union High School campus in West Woodstock which provides skating for visitors and residents alike throughout the season. Ice usually begins at this covered arena in October and runs through mid-March. Family and Senior Skating is popular as well as a variety of hockey matches throughout the season. Skate rentals and skating lessons for all ages are available. You can also rent skates at Woodstock Sports and Fine Clothing on Central Street in Woodstock No matter what the weather, you can enjoy this winter sport in Woodstock.