Singer-songwriter Judy Collins will be bringing her magic to the Town Hall Theatre in Woodstock on Sunday, December 22 at 7:30 PM.  A grammy-winning artist, Judy’s show is called “Holidays and Hits.”  We are thrilled to have such a famous iconic singer coming to our town!  Tickets are available at

Woodstock’s Wassail Weekend is one of Vermont’s top winter events. The village of Woodstock is beautifully decorated and welcomes visitors to its many shops and fine restaurants. It is the perfect time to escape before the rush of holiday preparations, and it will put you in the festive spirit!

Here are some of the events scheduled for the weekend at Pentangle. 

  • First is a concert titled “An Irish Christmas in America” which takes place on Friday, December 13 at 7:30 pm at the Town Hall Theater. 
  • On Saturday, December 14, you can take a holiday house tour and get the chance to visit some of the lovely historic homes in the village decorated for the season. 
  • Also on Saturday a traditional British afternoon tea takes place at St. James Church with two seatings. 

Tickets for all of these events are available at 

The annual Messiah Sing will take place on Sunday, December 15 at 4 PM at Our Lady of the Snows church (free with donations welcome). This is a hugely popular event and seats are limited so be sure to get there early!

Other Wassail Weekend events include the Woodstock Historical Society evening celebration on Friday evening, December 13 where visitors can see the beautifully decorated Dana House. 

Billings Farm is open for tours and sleigh or wagon rides, depending on weather. 

A highlight of the weekend is Saturday’s Parade of Horses and riders dressed in 19th century period dress which takes place around the Village Green. It is truly a magnificent sight. 

There is music and carol singing on the Green after the parade. 

A myriad of additional activities will take place during Woodstock’s Wassail Weekend including a crafts bazaar, concerts, poetry readings and music in the streets. More information about this very special celebration can be found at