Photo looking down a Woodstock, Vermont village sidewalk showling colorful storefronts all decorated for the Christmas season.

Woodstock–the prettiest small town in America.

Winter is upon us. Snow covers the ground here at the October Country Inn (check us out). The nearby Ottauquechee River has started to freeze over. The morning air has a bite that makes it especially welcome when the Winter sun shows itself. Christmas will be here soon but the second weekend in December is reserved for Vermont’s most iconic Winter event: the nearby village of Woodstock hosts it’s 35th annual Wassail Weekend. Wassail Weekend is an especially unique event for an especially unique Vermont village. Often named the prettiest small town in America, the village of Woodstock also hosts the best Christmas celebration in New England.

photo of a horse drawn wagon participating in Woodstock, Vermont's annual Wassail Parade.Wreathes and Christmas trees dot the village as the three-day festival prepares to celebrate traditional local culture. It’s a unique window into one of the many things that makes the Green Mountain State so special. A wide range of eclectic activities from craft fairs, to carol singing on the steps of the library, to ornament-making at Billings Farm & Museum, there’s something for everyone to enjoy. Many of Woodstock’s beautiful homes are opened to the public for charity and almost every local business and organization is involved in some way. In case you’re wondering what a Wassail might be, the word comes from a old Anglo-Saxon phrase which means “good health.”

Photo of Wassail Weekend participants warming themselves around a yule log campfire during a Winter sunset.

Getting warm around the yule log.

Originally, the wassail was a drink made of mulled ale, curdled cream, roasted apples, eggs, cloves, ginger, nutmeg, and sugar. It was served from huge bowls often made of silver or pewter.

The high point of Wassail Weekend is Saturday’s horse-drawn parade through downtown Woodstock that showcase local rural expertise and culture with more than fifty horses from all around the town and further afield taking part, the parade is truly a must-see. A performance by the Yale Whiffenpoofs, an internationally acclaimed group of a cappella singers will perform at the Woodstock Town Hall Theatre on Friday, Dec. 13. Established at Yale University in 1909, it is the oldest such group in the U.S.  At 2:00 p.m., on Saturday, Dec. 14, the Wassail parade invites you to line the streets around the village green for a cavalcade of clopping hooves, tossing manes, jolly jingling bells, tall top hats, flowing skirts, and merriness all around. Petite ponies and mighty Percherons pass by carrying their cargo of children in candy cane stockings, adults in historic finery, heavy carts, and Santa himself. Starting at the 3:00 p.m. first lighting, gather in the village green around the neatly stacked yule log. Check the Woodstock Chamber website for a complete listing of all the many ways to enjoy the holidays, as well as parking and shuttle information.