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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 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...

  • A number of rare books are arranged on a table
    Rare & Vintage Book Sale

    Rare & Vintage Book Sale

    Norman Williams Public Library 10 The Green, Woodstock, VT, United States

    Wassail Rare & Vintage Book Sale Just in time for the holidays, Norman Williams Public Library is offering an intriguing collection of rare and vintage books — a special two-day...

  • 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...

  • 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...

  • Public Skate at Union Arena

    Public Skate at Union Arena

    Union Arena 80 Amsden Way, Woodstock, Vermont

    Public Skate sessions are open to the public and a great way to have fun with family and friends. *Schedule Subject to Change* Public Skate Rates - Adult (ages 13 &...

    $5.00 – $8.00

  • Children’s Stories for December Holidays @ NWPL

    Norman Williams Public Library 10 The Green, Woodstock, VT, United States

    Children’s Stories for December HolidaysJoin us for a lively reading of storybooks celebrating the season. We’ll gather on the Mezzanine right after school at 3 pm and begin the stories...

  • 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 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...

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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