12 December Events: Killington Cup, Wassail Weekend, Cookies For Santa, New Year's Eve Gala & More

Nov 25, 2019 03:04PM ● By Erin Frisch

Fill up your calendar and kick off the holiday season with these fun events and activities taking place this December in Woodstock and the surrounding areas. Happy Holiday's!

Outdoor & Entertainment

The 2019 Homelight Killington Cup - start Nov 27 2019 1200PM

The 2019 Homelight Killington Cup: Dec 1, 2019 12:00PM

Live Music, Food, Skiing and so much more! Don't miss out on all the fun! The 2019 Homelight Killington Cup returns to Killington Resort, Nov. 27-Dec 1 with the women’s Audi FIS Ski World... Read More »

Holiday Cheer Craft Fair in Sharon - start Dec 07 2019 0900AM

Holiday Cheer Craft Fair in Sharon: Dec 7, 2019 09:00AM

Craft and food vendors, a free community meal from 11:30 a.m.-1 p.m. and craft activities with hot chocolate and books for the children. Contact Danielle Bird at 802-763-2372 or Donna Fos... Read More »

Wassail Weekend - start Dec 13 2019 1000AM

Wassail Weekend: Dec 13, 2019 10:00AM

Filled with twinkling lights, historic decorated homes, breakfast with Santa, and so much more, the town transforms into the holiday wonderland of your dreams, complete with sleigh bells ... Read More »

Wassail Weekend Whiffenpoofs - start Dec 13 2019 0730PM

Wassail Weekend Whiffenpoofs: Dec 13, 2019 7:30PM

Join us for a festive kick-off to Wassail Weekend with an exclusive live concert by the Whiffenpoofs, the internationally acclaimed a cappella singers from Yale University. About the Whi... Read More »

Cig Holiday Concert - start Dec 14 2019 0800PM

Còig Holiday Concert: Dec 14, 2019 8:00PM

Còig is one of Atlantic Canada’s most exciting Celtic traditional groups made up of four accomplished multi-instrumentalists, Chrissy Crowley, Rachel Davis, Darren McMullen, and Jason Roa... Read More »

Winter Solstice Party - start Dec 21 2019 0200PM

Winter Solstice Party: Dec 21, 2019 2:00PM

Join us for an afternoon of events at Suicide Six to celebrate the Winter Solstice and Holiday Vacation Week! There will be fat biking, local beers flowing, great food, sledding and live m... Read More »

Festivus Rail Jam - start Dec 28 2019 0200PM

Festivus Rail Jam: Dec 28, 2019 2:00PM

Festivus; A Rail Jam for the restuvus! An inaugural rail jam set up under lights on the bottom of Lasky’s so spectators can enjoy the action along with competitors! Open to skiers and r... Read More »

New Years Eve Gala Dinner - start Dec 31 2019 0600PM

New Year's Eve Gala Dinner: Dec 31, 2019 6:00PM

Join us for a splendid 4-course meal in the Rockefeller Room before you head down to the Ballroom to dance 2019 away to the live band at the NYE Gala! Dessert to be served downstairs in t... Read More »