Christmas towns in Vermont — could anything evoke a more charming, heartwarming image? You haven’t truly experienced an old-fashioned Christmas until you visit Vermont. The quiet charm of the small towns comes even more alive during the winter. A Woodstock Christmas is unlike any other. Full of enchantment and spirited traditions, this small town transforms into a festive wonderland every holiday season.

From December 8 - 10, 2023, the Annual Wassail Weekend will turn the delightful town of Woodstock into a Christmas wonderland. Immerse yourself in the spirit of the holidays during this three-day celebration.
Facebook/Billings Farm & Museum
Twinkling lights, lumieres, and greenery spruce up the town for the long weekend full of celebration. Concerts, storytelling, an artisan market, and bucketloads of other activities keep the whole family entertained.
Facebook/Billings Farm & Museum
One of the highlights of the weekend is the annual holiday parade. Enjoy the beautiful horses and bright costumes from a front-row seat on the village green.
Facebook/Billings Farm & Museum
Of course Santa with his silver bells also makes an appearance during the parade.
Facebook/Billings Farm & Museum
Get in the spirit with plenty of tunes belted out by local musicians.
Facebook/Billings Farm & Museum

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Residents and visitors alike put on their most Christmassy apparel and participate in Wassail weekend.
Facebook/Billings Farm & Museum
Stores and homes are decked out in their finest for the occasion. Nearby Billings Farm Museum is decorated in full 19th-century finery and welcomes visitors to stop by.
Facebook/Billings Farm & Museum
A huge bonfire keeps the center of town glowing with warmth.
Facebook/Billings Farm & Museum
Visit the outdoor cafe on the village green for seasonal favorites such as Wassail, chili, and mac and cheese. Indoors you can browse the craft fair, attend the silent auction, or take the kids to make crafts.
Facebook/Billings Farm & Museum
Join the town in singing traditional carols and songs. There are also plenty of concerts going on around town.
Facebook/Billings Farm & Museum
A Woodstock Christmas captures the essence of the holiday season. Make your plans now to visit this quintessential New England town.
Facebook/Billings Farm & Museum
Wassail Weekend will take place from December 8 - 10, 2023 from 10 a.m. - 7:30 p.m. daily. To take a closer look at what makes this event so memorable, you can watch the brief video below, courtesy of the Billings Farm & Museum:

Have you ever experienced a Woodstock Christmas? Let us know! If you need more information about the event, be sure to check out the official Woodstock, Vermont visitor’s site. While you’re in town, you’ll want to pay a visit to Vermont’s oldest family-run general store. And, if you need a cozy place to stay while you’re exploring the area, don’t forget to check out these unique cabin rentals in Woodstock, Vermont.

Do you have any other Christmas towns in Vermont that you consider a must-visit? If so, feel free to share them with us — we would love to hear from you!

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More to Explore

Winter In Vermont

Beth C. | November 06, 2023

What are some of the most charming Christmas towns in Vermont?

Vermont is absolutely magical during the holiday season. Below you'll find a list of some of the most charming Christmas towns in Vermont:

  • Woodstock
  • Stowe
  • Burlington
  • Grafton
  • Manchester
  • Chester
  • Weston
  • Middlebury

 

Let's face it: anywhere you travel in Vermont over the holidays is bound to be magnificent. If you're curious to learn more about any of the towns we mentioned above, be sure to check out our full article detailing some truly enchanting Christmas towns in Vermont.

What is there to do in Vermont in the winter?

There are so many activities to enjoy in Vermont in the wintertime, including any of the following:

  • A Traditional Christmas in Stowe

  • Castleton Christmas Market

  • Winter Lights at Shelburne Museum

  • Holidays on the Marketplace

  • Woodstock

  • Manchester

  • Grafton

  • Bolton Valley Backcountry and Nordic Sports Center

  • Stowe Mountain Resort

  • Mount Snow

  • Jay Peak Resort

  • Trapp Family Lodge

  • Leonard’s Log Cabin

  • Vermont Tree Cabin on Walker Pond

  • Tiny Cottage at Lake Eden

As you can see, there's so much to enjoy during the holiday season in the Green Mountain State. Looking for more information? We've compiled a list of the ultimate winter activities in Vermont -- there's something for everyone!

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