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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 lively, festive dancefloor scene at the Cabaret

    Holiday Cabaret 2025

    115 North Rd. 115 North Rd., Barnard, VT, US

    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 Town Hall (115 North Rd., Barnard)  Tickets: $35 plus optional additional donation to BarnArts end-of-year driveIncludes nibbles & dessert bars with coffee & tea. Cash bar

  • Vermont Comedy Festival: Judy Gold

    31 The Green 31 The Green, Woodstock, VT, United States

    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 part of Netflix’s Stand Out: An LGBTQ+ Celebration. She is the author of Yes I Can Say That: When.  Lobby opens at 7pm for drinks.

  • Woman carrying a pan of small soufflés just out of the open oven
    The Soufflé Also Rises and Apples in Pastry, Cooking Class

    The Soufflé Also Rises and Apples in Pastry, Cooking Class

    Bridgewater Corners Bridgewater Corners, Bridgewater Corners, VT, United States

    Having owned a restaurant named Hemingway's, we couldn't resist the title. Because we love cooking parties this is just one of many you can have here at our mountain-top retreat. Though Chef Ted can teach almost anything food-related, for this event you'll learn hands-on the secrets to making a delicious soufflé and more. First, we handle...

  • 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, VT, United States

    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...

  • Small Works
    Small Works Gallery Exhibit

    Artistree Small Works Gallery Exhibit

    2095 Pomfret Road 2095 POMFRET ROAD, South Pomfret, VT, United States

    Small Works: An annual holiday exhibit featuring artworks and fine crafts that celebrate the season. Opening Reception: Friday, November 14th from 5:30-7:30pm The Small Works exhibit features size-restricted 2-D and...

  • Close-up of a rooster amongst a flock

    Sensory Story Hour at Billings Farm: Chickens

    69 Old River Rd 69 Old River Rd, Woodstock, VT, United States

    Get ready to discover the world of eggs and learn all about chickens! Young learners will explore which animals lay eggs and enjoy a farm-fresh tasting of Billings cheesy eggs. Sensory...

  • Small Works
    Small Works Gallery Exhibit

    Artistree Small Works Gallery Exhibit

    2095 Pomfret Road 2095 POMFRET ROAD, South Pomfret, VT, United States

    Small Works: An annual holiday exhibit featuring artworks and fine crafts that celebrate the season. Opening Reception: Friday, November 14th from 5:30-7:30pm The Small Works exhibit features size-restricted 2-D and...

  • Garnishing a bowl of fish stew
    Name That Fish Stew! Cooking Class

    Name That Fish Stew! Cooking Class

    Bridgewater Corners Bridgewater Corners, Bridgewater Corners, VT, United States

    Learn skills to clean and combine fish,  shellfish, and various vegetables for a delicious tasting New England seafood stew—and with variation also known as French bouillabaisse or Italian cioppino. At the ready is fresh...

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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