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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.

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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Seasonal Events & Holidays

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  • 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 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.

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

    Music by the River: Community Choir and Marc Berger

    Music by the River
    East End Park East End Park, 217-03 Maxham Meadow Way, Woodstock, VT

    After one of the most vibrant and well-attended seasons we’ve ever had on the river, Music By The River returns for Summer 2026—bringing community, celebration, and an eclectic lineup of artists...

  • 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.

  • Drone image of east end park with grassy lawn, amphitheater seating, and pergola alongside the river

    Ottauquechee River Trail Firecracker 5K Run/Walk

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

    Join us for the inaugural Ottauquechee River Trail (ORT) Firecracker 5K on Saturday, July 4th, 2026. Part of Woodstock’s 250th Celebration honoring the signing of the Declaration of Independence, the Firecracker 5K also will raise funds to support the ongoing maintenance of the Ottauquechee River Trail.  The Firecracker 5K is family-friendly, and the route is...

  • July 4th Kids Bike Parade

    The Green The Green, Woodstock, VT, United States

    Join the fun for the Kids Bike Parade starting at Woodstock Elementary School with decorations available at 10:30, parade begins at 11:00am and goes up to the Village Green.

  •  July 4th Kids Market on the Green

    The Green The Green, Woodstock, VT, United States

    Come support youth in the community at the Kids Market on the Green. The PTO will also have food available for sale.

  • July 4th Craft Fair

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

    Shop from local craft vendors on the Village Green.

  • The Green During Fall

    July 4th Community Dinner

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

    Join together with neighbors, friends, and community members for a special July 4th community dinner on the Village Green. Live music, food available for purchase, beverages and bar, and good old fashioned fun!

  • Rec Center Pool Party

    Woodstock Rec Center 54 River Street, Woodstock, Vermont

    Come join the party and swim for free at the Rec Center pool. Bring a picnic or enjoy snacks from the snack bar.

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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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