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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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  • 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

  • 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

  • O’Jizo with Matt & Shannon Heaton

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

    Hailing from Japan, O’Jizo specializes in Irish traditional music, and combines the musical talents of Kozo Toyota on flute, guitarist Koji Nagao, and Hirofumi Nakamura on bouzouki and accordion. Their...

    $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

  • The Faux Paws LIVE in concert

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

    From raging fiddle tunes, to saxophone solos and unrequited love songs, the music of The Faux Paws would be hard to pin down with standard genre descriptions. The trio’s contagious groove,...

    $30

  • Nashville American duo- Goldpine

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

    From Bristol Rhythm & Roots Reunion and the Kansas City Chiefs’ Arrowhead Stadium to listening rooms throughout the United States, husband-wife duo GOLDPINE has been offering their own brand of bold harmony-driven...

    $30

  • VT Symphony: Jukebox Quartet concert

    2095 Pomfret Rd, South Pomfret, VT 05067 2095 Pomfret Rd, South Pomfret, VT 05067, South Pomfret, VT, US

    Vermont Symphony’s Jukebox quartet honors the legacy of American folk traditions with Appalachian, bluegrass, spiritual, and classical-inspired music that invites listeners onto the proverbial porch. With Brooke Quiggins-Saulnier and Joana...

    $30

  • Bookstock Market

    An array of Book Authors, Artists and Food Vendors with live music on The Green organized by the Woodstock Area Chamber of Commerce, along side Bookstock's children tent and book sale.

  • Bookstock Market

    An array of Book Authors, Artists and Food Vendors with live music on The Green organized by the Woodstock Area Chamber of Commerce, along side Bookstock's children tent and book sale.

  • 2026 Covered Bridges Half Marathon Pasta Supper

    Saskadena Six Ski Area 247 Stage Rd, South Pomfret, Vermont, United States

    Get energized for the Covered Bridges Half Marathon at the annual Half Marathon Pasta Supper presented by the Woodstock Area Chamber of Commerce. The annual feast at Saskadena Six ski...

    Get Tickets $10.00

  • Concert attendees lounging at the East End Park during summer in Woodstock, VT.

    Music in the Park at East End

    East End Park East End Park, 217-03 Maxham Meadow Way, Woodstock, VT

    Music in the Park sponsored by Pentangle at the East End Park.  Food, beverages, and cotton candy available for purchase.

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    July 5th Fireworks

    Woodstock Union High School 100 Amsden Way, Woodstock, Vermont

    Celebrate July 4th weekend and the 250th celebration of the signing of the Declaration of Independence with fireworks at the Woodstock Union High School.  Tons of fun family-friendly activities including...

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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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