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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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Today

A young girl in winter clothing participates in a taper candle making activity

Winter Celebration at Billings Farm

69 Old River Rd 69 Old River Rd, Woodstock

Step into the wonder of a Victorian Holiday, as the farm is beautifully transformed with twinkling lights and natural décor. The Historic House will be adorned in traditional 19th-century holiday trim, with Interpreters on hand to share stories and traditions of holidays past.    Families can take part in timeless activities including candle dipping, apple tastings featuring...

Close-up of a bird in a nest
Woodstock Vermont Film Series Presents:”La Liga” and “Stories to Save Us: The Saltmarsh Sparrow”

Woodstock Vermont Film Series Presents:”La Liga” and “Stories to Save Us: The Saltmarsh Sparrow”

69 Old River Road 69 Old River Road, Woodstock

The film series opens with a celebration of Vermont filmmakers, featuring two powerful short films that highlight the artistry, compassion, and vision of local storytellers. La Liga shares the inspiring story of Vermont’s immigrant dairy workers who, amidst isolation and hardship, form a soccer league to build community and hope. The film reflects on resilience...

Billings-Fence

Family Night at Billings Farm with TCC

Billings Farm & Museum 69 Old River Road, Woodstock

An evening all about engagement and connecting through laughter, competition and many silly constructed games! Get a glimpse of the environment that TCC creates in their programming, make new connections and enjoy an evening of pure community fun! TCC is partnering with Billings Farm & Museum to host Family Night in their beautiful event space...

$40.00

A lively, festive dancefloor scene at the Cabaret

Holiday Cabaret 2025

115 North Rd. 115 North Rd., Barnard

BarnArts Holiday Cabaret kicks off a busy December with savory and sweet treats, dancing, and music by Speak Easy Prohibition Band with Samira Evans along with BarnArts performers.Saturday, December 67-10pmBarnard...

judy gold vermont comedy festival

Vermont Comedy Festival: Judy Gold

31 The Green 31 The Green, Woodstock

Get ready to laugh!  Pentangle Arts welcomes back Vermont Comedy Festival  with headliner Judy Gold!  Judy Gold has had stand-up specials on HBO, Comedy Central and LOGO, and was a...

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.

  • 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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