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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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Today

  • Wassail Green at night over head

    Wassail Artisan Market

    Friday December 12th 1-6PMSaturday December 13th 10AM-4PM Wassail Artisan MarketSponsored by The Woodstock Chamber of Commerce Local Artisan's selling their goods in the heart of the Village, located on the...

  • 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,...

  • Alice by Heart Musical

    In the rubble of the London Blitz of World War II, Alice Spencer’s budding teen life is turned upside down, and she and her dear friend Alfred are forced to...

  • horse-drawn sleigh ride at Billings Farm

    Wassail Weekend at Billings Farm

    69 Old River Rd 69 Old River Rd, Woodstock, VT, United States

    As Woodstock celebrates its 41st annual Wassail Weekend, Billings Farm & Museum invites guests to step back in time and experience the holiday spirit of the 1890s. Visitors can explore...

  • Small Works
    Small Works Gallery Exhibit

    Artistree Small Works Gallery Exhibit

    2095 Pomfret Road 2095 POMFRET ROAD, South Pomfret, VT, United States

    Small Works: An annual holiday exhibit featuring artworks and fine crafts that celebrate the season. Opening Reception: Friday, November 14th from 5:30-7:30pm The Small Works exhibit features size-restricted 2-D and...

  • VINS Lights
    Forest of Lights at VINS

    Forest of Lights at VINS

    VINS Nature Center 149 Natures Way, Quechee, Vermont

    Experience winter magic as thousands of lights transform the VINS Nature Center into an enchanted wonderland. Stroll through spectacular displays featuring this year’s new attractions: the Sparkle Dome, Fiery Tower,...

  • Wassail Opening Candlelight Walk

    03-217 Maxham Meadow Way 03-217 Maxham Meadow Way, Woodstock, VT, US

    New tradition here in Woodstock. Join us as we open Wassail Weekend in historic Woodstock with Pentangle’s Here We Go A-Wassailing, a festive community tradition that sets the joyful tone...

    Free
  • Creating a pizza
    That’s Amore! Pizza and Calzone Cooking Class

    That’s Amore! Pizza and Calzone Cooking Class

    Bridgewater Corners Bridgewater Corners, Bridgewater Corners, VT, United States

    Have fun creating your own pizzas! Though award-winning Chef Ted can teach you almost anything food related, for this event he leads a hands-on pizza and calzone class. You’ll learn how to: make fresh dough make shells for later use treat toppings make sauce fashion a calzone grill a pizza, weather permitting We’ll use mostly organic and regional ingredients...

  • Frisson Holiday Concert

    31 The Green, Woodstock Town Hall Theatre 31 The Green, Woodstock Town Hall Theatre, Woodstock, VT, United States

    One of America’s most celebrated chamber music groups, performing at Lincoln Center to Carnegie Hall, bring classical Holiday fair to the Historic Woodstock Town Hall Theatre! Frisson brings together some...

  • 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...

  • Strong & Slow Flow
    Strong & Slow Yoga

    Strong & Slow Yoga

    184 Hartland Hill 184 Hartland Hill, Woodstock, VT, US

    Join us for Strong & Slow Yoga on Saturdays, 10:00am at Wise Pines - 184 Hartland Hill Road, Woodstock, VT 05091. Whether you're a beginner or an experienced yogi, this class is designed to accommodate all levels. Come and enjoy a rejuvenating session of yoga in a welcoming and inclusive community setting. Instructor Chelsey Seering...

  • Wassail Weekend: Holiday Ornament Making for Families

    2095 Pomfret Road 2095 POMFRET ROAD, South Pomfret, VT, United States

    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 solo or team up with family and friends to craft one-of-a-kind decorations that will sparkle on your tree or make heartfelt handmade gifts. This merry...

Community Events

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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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