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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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Family and Kids

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  • Public Skate at Union Arena

    Public Skate at Union Arena

    Union Arena 80 Amsden Way, Woodstock, Vermont

    Public Skate sessions are open to the public and a great way to have fun with family and friends. *Schedule Subject to Change* Public Skate Rates - Adult (ages 13 &...

    $5.00 – $8.00
  • 1954 cover illustration of White Christmas movie

    White Christmas – The Film

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

    White Christmas (1954) is a classic American musical film directed by Michael Curtiz and starring Bing Crosby, Danny Kaye, Rosemary Clooney, and Vera-Ellen. The story follows two World War II...

  • 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, VT, United States

    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...

  • Family Night at Billings Farm with TCC

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

    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
  • 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...

  • Toddler Story Time at NWPL

    Toddler Story Time at NWPL

    Norman Williams Public Library 10 The Green, Woodstock, VT, United States

    Join the NWPL to read a few books on a theme of the week. Enjoy stories, socializing, and often a project tied into the theme. For young children ages 20...

  • VINS Lights
    Forest of Lights at VINS

    Forest of Lights at VINS

    VINS Nature Center 149 Natures Way, Quechee, Vermont

    Experience winter magic as thousands of lights transform the VINS Nature Center into an enchanted wonderland. Stroll through spectacular displays featuring this year’s new attractions: the Sparkle Dome, Fiery Tower,...

  • 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...

  • Alice by Heart Musical

    In the rubble of the London Blitz of World War II, Alice Spencer’s budding teen life is turned upside down, and she and her dear friend Alfred are forced to take shelter in an underground tube station. When the ailing Alfred is quarantined, Alice encourages him to escape with her into their cherished book and...

  • horse-drawn sleigh ride at Billings Farm

    Wassail Weekend at Billings Farm

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

    As Woodstock celebrates its 41st annual Wassail Weekend, Billings Farm & Museum invites guests to step back in time and experience the holiday spirit of the 1890s. Visitors can explore Victorian Christmas traditions, learn about the origins of Wassail, and view the authentically decorated Historic House. Hands-on activities include candle dipping, interactive butter making, and...

  • Wassail participants approach and interact with a carriage horse

    Carriage Rides through the Village

    Take a whimsical ride through our quaint Village, while the town is decorated like a hallmark Christmas Card.  Wassail Carriage Rides through the VillageFri, 1-3PM, Sat. 9:30AM-12:30PM, Sun 10AM-2PM, $10...

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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