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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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  • Uphill Club at Saskadena Six

    Uphill Club at Saskadena Six

    The S6 Uphill Club is perfect for adult skiers looking to add an uphill component to their skill set. Learn the ins and outs of skinning and ski touring from our experienced Snow Sports staff, including how to properly apply, remove, and store skins, along with efficient uphill (and downhill) techniques. Participants should have their...

  • Magic of Maple

    Magic of Maple
    Billings Farm & Museum 69 Old River Road, Woodstock, Vermont

    Enjoy a sweet taste of Vermont’s maple history with sugar on snow, children’s stories, crafts, and more for Magic of Maple, daily from February 14 – February 22, 10:00AM – 4:00PM. Explore the magic of maple while learning all about maple syrup traditions in Vermont and enjoy the beautiful farmstead in winter.  Sample maple syrup,...

  • 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. Public Skate Rates - Adult (ages 13 & up) $8.00 / Youth (ages 4-12) $6.00  / Seniors (ages 60+ ) $5.00Child (ages 3 and under) Free / Super Senior (ages 70+) Free Skate Rentals (Figure or Ice Hockey)...

    $5.00 – $8.00

  • Magic of Maple

    Magic of Maple
    Billings Farm & Museum 69 Old River Road, Woodstock, Vermont

    Enjoy a sweet taste of Vermont’s maple history with sugar on snow, children’s stories, crafts, and more for Magic of Maple, daily from February 14 – February 22, 10:00AM – 4:00PM. Explore the magic of maple while learning all about maple syrup traditions in Vermont and enjoy the beautiful farmstead in winter.  Sample maple syrup,...

  • Magic of Maple

    Magic of Maple
    Billings Farm & Museum 69 Old River Road, Woodstock, Vermont

    Enjoy a sweet taste of Vermont’s maple history with sugar on snow, children’s stories, crafts, and more for Magic of Maple, daily from February 14 – February 22, 10:00AM – 4:00PM. Explore the magic of maple while learning all about maple syrup traditions in Vermont and enjoy the beautiful farmstead in winter.  Sample maple syrup,...

  • 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 & up) $8.00 / Youth (ages 4-12) $6.00  / Seniors (ages 60+ ) $5.00Child (ages 3 and under) Free / Super Senior (ages 70+) Free Skate...

    $5.00 – $8.00

  • 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. Public Skate Rates - Adult (ages 13 & up) $8.00 / Youth (ages 4-12) $6.00  / Seniors (ages 60+ ) $5.00Child (ages 3 and under) Free / Super Senior (ages 70+) Free Skate Rentals (Figure or Ice Hockey)...

    $5.00 – $8.00

  • Uphill Club at Saskadena Six

    Uphill Club at Saskadena Six

    The S6 Uphill Club is perfect for adult skiers looking to add an uphill component to their skill set. Learn the ins and outs of skinning and ski touring from our experienced Snow Sports staff, including how to properly apply, remove, and store skins, along with efficient uphill (and downhill) techniques. Participants should have their...

  • 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. Public Skate Rates - Adult (ages 13 & up) $8.00 / Youth (ages 4-12) $6.00  / Seniors (ages 60+ ) $5.00Child (ages 3 and under) Free / Super Senior (ages 70+) Free Skate Rentals (Figure or Ice Hockey)...

    $5.00 – $8.00

  • Widestock – Fat Bike Festival

    Join Mountain Bike Vermont and Woodstock Area MTB Association (WAMBA) for our second annual fatbike fest in Woodstock, Vermont! Presented by the Woodstock Area Mountain Bike Association, von Trapp Brewing, Ranch Camp, and Mountain Bike Vermont, we're proud to bring you Woodstock's second annual fatbike festival! Join us Saturday, February 28th, 2026 for a day...

    $82

  • Maple Open House at King Farm

    King Farm King Farm Rd, Woodstock, Vermont, United States

    Join the CRAFT (Community and Climate Resilience through Agriculture,Forestry, and Technology) program of Woodstock Union High School andthe Vermont Land Trust at the historic King Farm in Woodstock for an (early) Maple Open House Weekend celebration.Explore the sweet tradition of Vermont maple sugaring with tours anddemonstrations at the sugarhouse and learn how sap becomes syrup....

  • O’Jizo with Matt & Shannon Heaton

    Artistree Community Arts Center 2095 Pomfret Road, South Pomfret, VT, United States

    Hailing from Japan, O’Jizo specializes in Irish traditional music, and combines the musical talents of Kozo Toyota on flute, guitarist Koji Nagao, and Hirofumi Nakamura on bouzouki and accordion. Their band name comes from blending syllables of each player’s name (hirO, koJI, koZO). And their music is a blend of old and new Irish tunes,...

    $30
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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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