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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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Events

Today

  • A lively, festive dancefloor scene at the Cabaret

    Holiday Cabaret 2025

    115 North Rd. 115 North Rd., Barnard, VT, US

    BarnArts Holiday Cabaret kicks off a busy December with savory and sweet treats, dancing, and music by Speak Easy Prohibition Band with Samira Evans along with BarnArts performers.Saturday, December 67-10pmBarnard...

  • Vermont Comedy Festival: Judy Gold

    31 The Green 31 The Green, Woodstock, VT, United States

    Get ready to laugh!  Pentangle Arts welcomes back Vermont Comedy Festival  with headliner Judy Gold!  Judy Gold has had stand-up specials on HBO, Comedy Central and LOGO, and was a part of Netflix’s Stand Out: An LGBTQ+ Celebration. She is the author of Yes I Can Say That: When.  Lobby opens at 7pm for drinks.

  • Close-up of a bird in a nest

    Woodstock Vermont Film Series Presents:”La Liga” and “Stories to Save Us: The Saltmarsh Sparrow”

    Woodstock Vermont Film Series Presents:”La Liga” and “Stories to Save Us: The Saltmarsh Sparrow”
    69 Old River Road 69 Old River Road, Woodstock, VT, United States

    The film series opens with a celebration of Vermont filmmakers, featuring two powerful short films that highlight the artistry, compassion, and vision of local storytellers. La Liga shares the inspiring story of Vermont’s immigrant dairy workers who, amidst isolation and hardship, form a soccer league to build community and hope. The film reflects on resilience...

  • Small Works

    Artistree Small Works Gallery Exhibit

    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 3-D artwork  and fine crafts by area local artists. Paintings and prints 144 square inches (12"x12") or smaller will be displayed for your holiday viewing (and...

  • Close-up of a rooster amongst a flock

    Sensory Story Hour at Billings Farm: Chickens

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

    Get ready to discover the world of eggs and learn all about chickens! Young learners will explore which animals lay eggs and enjoy a farm-fresh tasting of Billings cheesy eggs. Sensory Story Hour is a movement-rich, interactive experience designed for children ages 3-5 and their caregivers. Through stories, song, poetry, rhymes, sensory exploration, and farm-themed activities,...

  • Small Works

    Artistree Small Works Gallery Exhibit

    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 3-D artwork  and fine crafts by area local artists. Paintings and prints 144 square inches (12"x12") or smaller will be displayed for your holiday viewing (and...

  • 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. Public Skate Rates - Adult (ages 13 & up) $8.00 / Youth (ages 4-12) $6.00  / Seniors (ages 60+ ) $5.00Child (ages 3 and under) Free / Super Senior (ages 70+) Free Skate Rentals (Figure or Ice Hockey)...

    $5.00 – $8.00
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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