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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.

Events

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Today

  • Farm Friends Play Club at Billings Farm & Museum

    Farm Friends Play Club at Billings Farm & Museum
    Billings Farm & Museum 69 Old River Road, Woodstock, Vermont

    Join Farm Friends Play Club, a welcoming, hands-on, and screen free play experience on Saturdays! Using everyday materials, children can imagine, create, and play with their caregivers. It is a place to make new friends, explore together, and let curiosity lead the way. Designed primarily for children ages 3-9 and welcoming to siblings and family...

    $12 – $21

  • Bookstock

    Bookstock
    The Green The Green, Woodstock, VT, United States

    Bookstock, the Vermont Festival of Words, features author readings; a huge used book sale; poetry; workshops; events for children; food; and other festivities centered on Woodstock's Green. New in 2026: VT Youth Poet Laureate, VT Book Award winners, cookbook authors + restaurants!

    Free

  • Bookstock Market

    An array of Book Authors, Artists and Food Vendors with live music on The Green organized by the Woodstock Area Chamber of Commerce, along side Bookstock's children tent and book sale.

  • Spring Sidewalk Sale

    Spring Sidewalk Sales, enjoy discounts while browsing our unique downtown Woodstock merchants. Stroll through our beautiful village while the sun is shining. Over the same weekend as our Bookstock Market and all the Bookstock Events!

  • Tree display with picture books in library

    Family Story Time at NWPL

    Family Story Time at NWPL
    Norman Williams Public Library 10 The Green, Woodstock, VT, United States

    Grandparents, parents, and caregivers are invited to bring their young charges to enjoy stories. We’ll select picture books about the season, or a theme, or perhaps feature new additions to our collection. Everyone is welcome. Discover new picture books or savor old favorites with the younger family members. On the second Saturday of each month,...

  • Chef shows woman how to make a tortellini pasta

    Rid Your Pasta Performance Complex, Cooking Class

    Rid Your Pasta Performance Complex, Cooking Class
    Bridgewater Corners Bridgewater Corners, Bridgewater Corners, VT, United States

    Have a cooking pasta party! You'll have fun and learn to cook at our mountain-top idyll.  Chef Ted can teach almost anything culinary, and at this hands-on event you'll make a fresh tomato sauce, learn how to roll out ravioli, fashion tortellini, and make a perfect fettuccine Alfredo.  You're sure to fall in love with...

  • Bookstock Comes to Billings! Caleb Kenna Discussion and Book Signing

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

    Join photographer Caleb Kenna for an inspiring discussion on his photography book “Art from Above: Vermont”! Take a behind-the-scenes look at how Kenna captures Vermont’s beauty from the sky, revealing how striking aerial perspectives connect Vermont’s identity with its working landscapes. Take home a signed copy of his book and enjoy a drone demonstration at...

  • Lyle Brewer

    Guitarist Lyle Brewer

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

    Lyle Brewer is a virtuoso guitarist whose unique sound blends jazz, classical, folk, and blues influences. An integral part of the Boston music scene for well over a decade, he’s earned a reputation as one of today’s most versatile and expressive guitarists. Whether performing solo or with renowned artists such as Lake Street Dive, the...

    $25

  • Bookstock

    Bookstock
    The Green The Green, Woodstock, VT, United States

    Bookstock, the Vermont Festival of Words, features author readings; a huge used book sale; poetry; workshops; events for children; food; and other festivities centered on Woodstock's Green. New in 2026: VT Youth Poet Laureate, VT Book Award winners, cookbook authors + restaurants!

    Free

  • BarnArts Race Around the Lake 5K/10K Fundraiser

    Silver Lake State Park 250 North Rd., Barnard, VT, United States

    "The Most Beautiful Race in Vermont!" Sunday, May 17 10:30a (10K) & 11a (5K), at Silver Lake State Park. Runners (10K & 5K) and walkers (5K) circle Silver Lake on town roads, dirt roads and single-track wooded trails with intermittent views of the lake. Sign up by April 30 to get a free Race T-Shirt....

    $25 – $50

  • Bookstock Market

    An array of Book Authors, Artists and Food Vendors with live music on The Green organized by the Woodstock Area Chamber of Commerce, along side Bookstock's children tent and book sale.

Community Events

Have an upcoming event you’d like to share?

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.

Submit an Event

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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