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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 Vermont Mandolin Trio

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

    Listen to three of Vermont’s finest mandolinists for a rare evening of bluegrass, jazz and roots music in the unique (and very happy sounding) setting of three mandolins. The trio...

    $30

  • “Tie my own shoes” Comedy Night

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

    "Tie my own shoes" is a new show by comedian Vicki Ferentinos. Filled with fun stories, jokes and adventures about life lessons, epic fails and some unusual triumphs. Ferentinos has...

    $20 – $25

  • MUD (season) Exhibit Opening Reception

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

    As winter begins to loosen its grip, we welcome the return of the beloved annual MUD (season) Exhibit. This lively, joy-filled show features 2-D and 3-D work by more than 60 local artists, all inspired by the unmistakable signs of Vermont’s “fifth season” — melting snow, flowing sap, awakening wildlife, muddy backroads, and that magical...

  • Ashley Gutermuth Live at the Grange Theatre

    Ashley Gutermuth Live at the Grange Theatre
    Artistree Community Arts Center 2095 Pomfret Road, South Pomfret, VT, United States

    Ashley Gutermuth is coming to Vermont and she is bringing her hilarious friends! Described by The New York Times as a “comedian,” Ashley Gutermuth is a stand-up comedian, podcast host, and actor. She appeared on The Tonight Show Starring Jimmy Fallon, where Jerry Seinfeld selected her as the winner of the “Seinfeld Challenge.” Ashley performs...

    $25 – $30

  • Woodstock Vermont Film Series Screening of “Every Little Thing”

    Woodstock Vermont Film Series Screening of “Every Little Thing”
    Billings Farm & Museum 69 Old River Road, Woodstock, Vermont

    Every Little Thing follows author and wildlife rehabilitator Terry Masear on her heartfelt mission to save every injured hummingbird in Los Angeles. Amidst the city’s chaos, Terry tends to her fragile, feathered patients with extraordinary care. Through slow-motion imagery and tender storytelling, director Sally Aitken invites us into the delicate world of birds, celebrating their tiny...

    $12 – $15

  • Ashley Gutermuth Live at the Grange Theatre

    Ashley Gutermuth Live at the Grange Theatre
    Artistree Community Arts Center 2095 Pomfret Road, South Pomfret, VT, United States

    Ashley Gutermuth is coming to Vermont and she is bringing her hilarious friends! Described by The New York Times as a “comedian,” Ashley Gutermuth is a stand-up comedian, podcast host, and actor. She appeared on The Tonight Show Starring Jimmy Fallon, where Jerry Seinfeld selected her as the winner of the “Seinfeld Challenge.” Ashley performs...

    $25 – $30

  • Art on the Barns

    Art on the Barns
    Billings Farm & Museum 69 Old River Road, Woodstock, Vermont

    Wander through the farm and discover a bold outdoor art exhibition installed across its historic buildings. Moving beyond traditional gallery walls, this contemporary exhibition comes to life as the colors,...

    $12 – $21

  • Glitchy Business with Cindy Pierce

    Glitchy Business with Cindy Pierce
    Artistree Community Arts Center 2095 Pomfret Road, South Pomfret, VT, United States

    “Let me add to the heap of praise about Cindy’s show. What a messenger, Pierce, who grew up in Hanover and graduated from UNH, is known for her fearless personality...

    $20 – $25
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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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