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Seasonal Events & Holidays

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.

Seasonal Events & Holidays

Events

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Today

  • 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

  • WAMBA Trail Work Day

    Ready to get outside and experience the craft of trail building? The Woodstock Area Mountain Bike Association invites you to a trail work day at Knox Meadow in the Mt....

    Free

  • 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...

  • Forest Stewards Guild Gathering at Hawkes Tree Farm

    Wayside Rd Wayside Rd Extension, Woodstock, VT, United States

    Join the Forest Stewards Guild for a lively Guild Gathering at the Hawkes Family Tree Farm in scenic Woodstock, Vermont!   Longtime Guild member Gerry Hawkes has been honored with the 2025...

    Free

  • Spring Sidewalk Sale

    Spring Sidewalk Sales, enjoy discounts while browsing our unique downtown Woodstock merchants. Stroll through our beautiful village while the sun is shining. Over the same weekend as our Bookstock Market...

  • 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...

  • Woodstock Garden Day

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

    Explore three stunning gardens in sites across Woodstock. Discover the shared story between Marsh-Billings-Rockefeller National Historical Park, Billings Farm & Museum, and the Woodstock Inn & Resort’s Kelly Way Gardens. Enjoy garden...

  • Opening of the Fairway Grill

    The Woodstock Country Club 76 South St, Woodstock, Vermont, United States

    Kick off Memorial Day Weekend with the opening of the Fairway Grill at the Woodstock Country Club! Join us for relaxed lunches, handcrafted cocktails, and scenic views overlooking the greens as...

  • 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...

  • 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...

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

What would you like to do today?

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

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Mt. Peg Bike Riders

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