Stop by Sunday Drive for Wassail Weekend!

Looking for a fun way to kick off the holidays this weekend? As we approach the end of another year, Woodstock, Vermont, transforms into a winter wonderland filled with historical charm with the 40th Annual Wassail Weekend. This cherished event marks the beginning of the holiday season with an array of activities that capture the essence of New England’s festive charm during this time of year. Let’s dive into what you can expect during this always anticipated community event this weekend. 

Shop Now

Wassail Weekend: A Festive Holiday and Winter Tradition

Wassail Weekend is not just an event; it’s a tradition that weaves together the community’s love for winter, music, community, and celebration. From December 13th to December 15th, Woodstock’s streets are lined with twinkling lights, and historic homes are fully decked out with holiday decorations, creating a scene straight out of a storybook.

Beyond the scenery, however, visitors can enjoy everything from a parade and carriage rides to arts and crafts and a bonfire, not to mention the annual lighting of the tree. Events are available for people of all ages, including kids.

Additionally, from the Artisan Fair to food trucks, Wassail Weekend is the perfect time to support local businesses. So, whether you go for the live music, the parade, the food, or otherwise, you’re bound to enjoy your visit and get some of the best VT has to offer during your visit.

Wassail Weekend Woodstock: Highlights of the Event

Friday 12/13 at 5 p.m.

On Friday, December 13th the festivities kick off with the opening ceremony at 5:00 pm. In the evening, you can get cozy and enjoy a classic show with “A Classical Christmas” by Frisson at the Woodstock Town Hall Theatre. This concert features holiday classics performed by some of the region’s finest musicians, offering a perfect prelude to the weekend’s festivities.

Saturday, 12/14 at 2 p.m.

The main event, the 40th Annual Wassail Parade, starts at 2 p.m., where you’ll see horse-drawn carriages, carolers, and festive floats circling the Village Green. Before the parade, explore the Artisan and Food Market under the Middle Covered Bridge, where local artisans showcase their crafts and treats.

After the Parade

Catch the Hot Cocoa & Donut Bar on the Front Lawn. Grab some warm, comforting cocoa or cider and delicious donuts at the Woodstock Inn & Resort’s Front Lawn. As the sun sets, there’s a tree lighting and a bonfire where community members gather to sing carols and enjoy the closing of the event.

Planning Your Visit to Wassail Weekend

Here are just a few things to know before heading to Wassail Weekend in Woodstock, VT:

• Dress in Layers: Vermont’s winters are beautiful but cold, especially during December, so be sure to wear thermal layers, a warm coat, hat, gloves, and insulated boots.
• Book in Advance: Secure spots for any fee-based events, local hotels or Airbnbs, or special activities early to get to enjoy the weekend to the fullest.
• Use the Shuttle: Enjoy the free shuttle service on Saturday to visit all the event locations.
• Parking Tips: Opt for the free parking at the Woodstock High School and use the shuttle service to avoid the hassle of finding a spot in the village.
• Pets Are Welcome: Pets are welcome to outdoor events as long as they are kept on a leash and cleaned up after along the way.
• Check Out the Schedule: Wassail Weekend is full of events and festivities, far too many to list here. Therefore, to get to see and do everything you want, be sure to look at the full schedule of events and plan accordingly.

Visit the Wassail Weekend Dispensary: Sunday Drive

At Sunday Drive, Woodstock’s own cannabis dispensary, we are thrilled to be part of this year’s Wassail Weekend and one of the communities’ most appreciated annual traditions. Our location in the heart of Woodstock means you’re just a short drive from the best cannabis in town if heading out to enjoy the festivities.

Whether you’re looking to enhance your experience with cannabis or looking for something to take home after, we’ve got you covered. Don’t forget, you can also order via our online menu to make pickup quick and easy along the way.

Shop Now