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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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Live Music & Concerts

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  • 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...

  • Wrensong Presents “Songs of Celebration Through the Centuries”

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

    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...

  • The Harvard Krokodiloes A Cappella Group

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

    The world renown a Cappella Group joins us with the Blue Streak Quartet Opening! A wonderful addition to our Wassail Weekend! The Krokodiloes are Harvard's oldest acapella group, blending choreography,...

  • Wassail Weekend: Holiday Music in the Hayloft

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

    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...

  • The Messiah – Sing-Along

    7 South Street 7 South Street, Woodstock, VT, United States

    “The Messiah” – Presented at Our Lady of the Snows Church, featuring professional musicians and local talent. Come join in on this family tradition for over 50 years. Lobby opens...

    Free

  • BarnArts Winter Carols 2025

    6211 VT Rt. 12 6211 VT Rt. 12, Barnard, VT, US

    BarnArts original event, Winter Carols, is a free & festive opportunity to join with neighbors and friends and celebrate the season as a community! Winter Carols includes audience sing-alongs as...

  • Jazz Jam at the library

    Interplay Jazz Jam Session: Library After Hours

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

    Musicians and listeners are invited to enjoy this Interplay Jazz Jam Session on the Mezzanine with its great acoustics and grand piano.

  • Rumney Sessions at Fable Farm

    Rumney Sessions at Fable Farm
    Fable Farm 1525 Royalton Turnpike, South Royalton, Vermont

    Much like Feast & Field, these Thursday evenings bring together farm food, art, and community—but in a smaller, cozier setting. Tucked inside a 250-year-old barn, these gatherings offer a warm and welcoming...

    $10 – $30

  • Ben Kogan Band

    Artistree Community Arts Center 2095 Pomfret Road, South Pomfret, VT, United States

    Jammy Roots Rock The Ben Kogan Band jammy roots rock with jazz and bluegrass sensibilities. Known for heartfelt lyrics and high-energy shows, Ben and his band have been lighting up local stages with...

    $30

  • Rumney Sessions at Fable Farm

    Rumney Sessions at Fable Farm
    Fable Farm 1525 Royalton Turnpike, South Royalton, Vermont

    Much like Feast & Field, these Thursday evenings bring together farm food, art, and community—but in a smaller, cozier setting. Tucked inside a 250-year-old barn, these gatherings offer a warm and welcoming...

    $10 – $30
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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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