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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.

Planning ahead? See our annual events here, and check out our blog for more itineraries and things to do in Woodstock.

Would you like to share a community event for publication on our site? Submit events here.

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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...

  • 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,...

    $82

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    12U Tier 3 Regional Hockey Tournament

    Union Arena 80 Amsden Way, Woodstock, Vermont

    Come to Union Arena to watch the top 12U Tier 3 hockey teams from Vermont (Woodstock Jr. Wasps), Maine, New Hampshire, Connecticut, and Rhode Island

  • WAMBA Trail Work Day

    Ready to get outside and experience the craft of trail building? The Woodstock Area Mountain Bike Association invites you to a trail work day at Knox Meadow in the Mt....

    Free

  • Ottauquechee River Trail Firecracker 5K Run/Walk

    Ottauquechee River Trail 0 Maxham Meadow Way, Woodstock, Vermont

    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...

Community Events

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Take a few moments to tell us about your event by clicking the button here and using our Community Events Submission form. You’ll need to create an account on our site to share an event. Follow the steps on the Events Submission page to get started.

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

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Mt. Peg Bike Riders

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