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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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Arts, Film & Culture

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  • The Art of Dining

    The Art of Dining
    Barnard Town Hall 115 North Rd., Barnard, VT, United States

    The Art of Dining By Tina Howe Directed by Linda Treash Fridays & Saturdays, March 20-21 & 27-28 –7:30pm Sundays, March 22 & 29 –2pm Thursday, March 26 –7:30pm Barnard...

    $15 – $20

  • Escape to Create (21+) at Billings Farm

    Billings Farm & Museum 69 Old River Road, Woodstock, Vermont

    Welcome to TCC's first 21+ Community Event Escape the doldrums and join us for an evening of connection and creativity! Expect to feel inspired during a TCC-style art experience, while...

    $50.00
  • portrait of Ira Allen

    Kevin Graffagnino – Ira Allen and the Green Mountain Frontier

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

    Land speculator, revolutionary, politician, and empire builder, Ira Allen. a key figure on the Green Mountain frontier, helped create and sustain the independent State of Vermont.

  • Sheep Shearing at Billings Farm & Museum

    Billings Farm & Museum 69 Old River Road, Woodstock, Vermont

    Come watch the farm’s sheep and goats get their spring haircuts! Witness the skill and care behind this seasonal tradition, learn how shearing tools and techniques have evolved over time,...

    $12 – $21
  • Word Games @ NWPL

    Word Games! | “Library After Hours”

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

    Calling all crossword puzzlers, Wordle fans, spelling bee champs: time to relax, mingle, and play games!

  • Baby Farm Animal Celebration

    Baby Farm Animal Celebration
    Billings Farm & Museum 69 Old River Road, Woodstock, Vermont

    Don’t miss the cutest event of the year! This fun-filled weekend offers a special opportunity to interact with the farm’s newest and cutest arrivals, meet farmers, and experience the wonders...

  • Baby Farm Animal Celebration

    Baby Farm Animal Celebration
    Billings Farm & Museum 69 Old River Road, Woodstock, Vermont

    Don’t miss the cutest event of the year! This fun-filled weekend offers a special opportunity to interact with the farm’s newest and cutest arrivals, meet farmers, and experience the wonders...

  • painting of a battle

    Howard Coffin – The Great Bennington Battle and Vermont |

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

    The surrender at Saratoga of a British army has long been called the decisive battle of the American Revolution, but perhaps John Burgoyne was doomed two months earlier at the Battle of Bennington.

  • Bookstock

    Bookstock
    The Green The Green, Woodstock, VT, United States

    Bookstock, the Vermont Festival of Words, features author readings; a huge used book sale; poetry; workshops; events for children; food; and other festivities centered on Woodstock's Green. New in 2026:...

    Free

  • Bookstock

    Bookstock
    The Green The Green, Woodstock, VT, United States

    Bookstock, the Vermont Festival of Words, features author readings; a huge used book sale; poetry; workshops; events for children; food; and other festivities centered on Woodstock's Green. New in 2026:...

    Free
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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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