woodstock Vermont downtown awaits Wassail Weekend.

Woodstock–the prettiest small town in America.

Winter is upon us in Woodstock, Vermont, and that means Wassail Weekend. Snow covers the ground here at the October Country Inn. The nearby Ottauquechee River has started to freeze over.  And the morning air’s bite  makes it especially welcome when the Winter sun shows itself. Christmas will be here soon.  Most importantly, Vermont’s most iconic Winter event occurs the second weekend in December.  This is when the nearby village of Woodstock hosts it’s 35th annual Wassail Weekend.

Prettiest Small Town in America

Wassail Weekend is an especially unique event for an especially unique Vermont village. Named the prettiest small town in America, Woodstock also hosts the best Christmas celebration in New England.

Wassail is from a phrase meaning “good health.”

horse drawn Wassail Weekend parade Wagon in Woodstock VermontWreathes and Christmas trees dot the village as the three-day Wassail weekend 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 open to the public.  Almost every local business and organization is involved in some way. In case you’re wondering.  The word Wassail comes from a old Anglo-Saxon phrase which means “good health.”

The Wassail Weekend Yule log in Vermont

Getting warm around the yule log.

Wassail Weekend History

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. 

Join us in Vermont for Wassail Weekend

At 2:00 p.m., on Saturday, Dec. 14, the Wassail weekend 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.