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Woodstock’s rich heritage and culture come alive during special events and annual celebrations that are packed with New England flair. From intimate, farm-to-table parties to winter festivals, come discover what makes the Woodstock area such an inspiring place to visit.

Looking for more information on an an event not listed below? Check out our blog for more itineraries and things to do in Woodstock.

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Wassail Weekend

Woodstock gets into the holiday season during Wassail Weekend, a celebration of the sights, sounds, and spirit of winter. Take in the magic of twinkling light displays, decorated historic homes,...

Wassail participants approach and interact with a carriage horse

Carriage Rides through the Village

Take a whimsical ride through our quaint Village, while the town is decorated like a hallmark Christmas Card. Wassail Carriage Rides through the VillageFri, 1-3PM, Sat. 9:30AM-12:30PM, Sun 10AM-2PM, $10 personMeet...

artistree ornament making

Wassail Weekend: Holiday Ornament Making for Families

2095 Pomfret Road 2095 POMFRET ROAD, South Pomfret

Celebrate the magic of Wassail Weekend with a joyful, hands-on workshop for all ages! ?✨ Create your own collection of whimsical holiday ornaments at a variety of festive art stations—work...

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Wassail Cafe

Wassail Beverages on the Green! Come quench your thirst with our festival holiday drink (adult & non). $$ Card or Cash 

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Wassail Holiday Craft Fair

Wassail Holiday Craft Fair

Masonic Hall 30 Pleasant Street, Woodstock

The 20th annual Woodstock Wassail Holiday Craft Fair will take place at the Masonic Hall at 30 Pleasant Street. There is no admission fee. There are wide variety of wonderful local...

norman williams public library

Wrensong Presents “Songs of Celebration Through the Centuries”

Norman Williams Public Library 10 The Green, Woodstock

Wrensong Presents “Songs of Celebration Through the Centuries” A Wassail tradition returns with a sampler of holiday songs performed by Wrensong on the Mezzanine at the Norman Williams Public Library...

Wassail Weekend luminaries

Lighting of the Luminaries

Come walk the green, while the sun goes down and admire the luminaries lighting up the pathway. Sponsored by the Woodstock Rotary Club 

holiday music at artistree

Wassail Weekend: Holiday Music in the Hayloft

2095 Pomfret Road 2095 POMFRET ROAD, South Pomfret

Celebrate the season with a joyous evening of music and togetherness at our annual Christmas concert! Celebrate Woodstock’s Wassail Weekend in style with an evening of jazz and festive cheer at...

Community Events

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Take a few moments to tell us about your event by clicking the button here and using our Community Events Submission form. You’ll need to create an account on our site to share an event. Follow the steps on the Events Submission page to get started.

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Seasonal Feature

There is something for everyone regardless of the season. From fall foliage guides to winter traditions to spring rebirth and summer adventures, explore the latest that celebrates the best of Woodstock right now.

  • Around Town Holidays
    How to Enjoy the Holiday Season in Woodstock
    Woodstock, Vermont, offers a captivating holiday journey, intertwining age-old traditions with modern charm. Revel in the vibrant festivities of a New England Thanksgiving, Wassail Weekend, or explore artisanal treasures in local shops, and bask in winter’s serenity or adventures outdoors.
    Read article

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