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Markets & Festivals

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.

Planning ahead? See our annual events here, and check out our blog for more itineraries and things to do in Woodstock.

Would you like to share a community event for publication on our site? Submit events here.

Markets & Festivals

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  • Wassail Green at night over head

    Wassail Artisan Market

    Friday December 12th 1-6PMSaturday December 13th 10AM-4PM Wassail Artisan MarketSponsored by The Woodstock Chamber of Commerce Local Artisan's selling their goods in the heart of the Village, located on the Village Green.

  • Wassail Holiday Craft Fair

    Wassail Holiday Craft Fair
    Masonic Hall 30 Pleasant Street, Woodstock, Vermont

    The 20th annual Woodstock Wassail Holiday Craft Fair will take place at the Masonic Hall at 30 Pleasant Street. There is no admission fee. There are wide variety of wonderful local makers who have been working hard to make special gifts for your special someone. Come do a little holiday shopping with local artisans! We hope...

  • Wassail Holiday Craft Fair

    Wassail Holiday Craft Fair
    Masonic Hall 30 Pleasant Street, Woodstock, Vermont

    The 20th annual Woodstock Wassail Holiday Craft Fair will take place at the Masonic Hall at 30 Pleasant Street. There is no admission fee. There are wide variety of wonderful local makers who have been working hard to make special gifts for your special someone. Come do a little holiday shopping with local artisans! We hope...

  • 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 of farm life firsthand! Enjoy horse-drawn wagon rides and explore engaging hands-on activities, including animal-themed crafts and games. Sample Billings Farm cheeses, grab a bite...

  • 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 of farm life firsthand! Enjoy horse-drawn wagon rides and explore engaging hands-on activities, including animal-themed crafts and games. Sample Billings Farm cheeses, grab a bite...

  • 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: VT Youth Poet Laureate, VT Book Award winners, cookbook authors + restaurants!

    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: VT Youth Poet Laureate, VT Book Award winners, cookbook authors + restaurants!

    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: VT Youth Poet Laureate, VT Book Award winners, cookbook authors + restaurants!

    Free

  • Mt. Tom Farmer’s Market

    Mt. Tom Farmer’s Market
    Saskadena Six 247 Stage Road, Pomfret, United States

    The Mt Tom Farmers Market at Saskadena Six will run Saturday mornings, 9:30am-12:30pm, rain or shine from May 23, 2026 to October 10, 2026. The market is in its 41st year and this year we have 20+ vendors--farmers, makers and bakers.  Vendors

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.

  • The Ultimate Guide to Mountain Biking in Woodstock, VT
    Casuals, pros, group riders, kids and families… get ready to shred.
    Read article

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

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