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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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  • Ham Gillett presents Dylan Thomas’s Lyrical Portrait of Holidays Past

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

    A Traditional Reading at NWPL...Send the kids to romp outside, take off your apron, stash the light-hanging ladder, and join us on Saturday, December 13, from 12:00-12:30 OR 1:00-1:30 for Ham Gillett’s traditional Wassail reading.The Welsh poet, Dylan Thomas, looks back with a child’s-eye view of a magical time of presents, family, and newly fallen...

  • Wassail Horse Parade

    Join us for the 41st Annual Wassail Horse Parade where we will have 40 participates decked out in Victorian gear and Holiday Cheer. Lead by the Brattleboro American Legion Band,...

  • Wrensong Presents “Songs of Celebration Through the Centuries”

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

    Wrensong Presents “Songs of Celebration Through the Centuries” A Wassail tradition returns with a sampler of holiday songs performed by Wrensong on the Mezzanine at the Norman Williams Public Library...

  • Lighting of the Luminaries

    Come walk the green, while the sun goes down and admire the luminaries lighting up the pathway. Sponsored by the Woodstock Rotary Club 

  • 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...

  • The Harvard Krokodiloes A Cappella Group

    31 The Green, Woodstock Town Hall Theatre 31 The Green, Woodstock Town Hall Theatre, Woodstock, VT, United States

    The world renown a Cappella Group joins us with the Blue Streak Quartet Opening! A wonderful addition to our Wassail Weekend! The Krokodiloes are Harvard's oldest acapella group, blending choreography,...

  • Wassail Weekend: Holiday Music in the Hayloft

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

    Celebrate the season with a joyous evening of music and togetherness at our annual Christmas concert! Celebrate Woodstock’s Wassail Weekend in style with an evening of jazz and festive cheer at...

  • 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 personMeet in front of TD Bank

  • Wassail Holiday Craft Fair

    Wassail Holiday Craft Fair

    Masonic Hall 30 Pleasant Street, Woodstock, Vermont

    The 20th annual Woodstock Wassail Holiday Craft Fair will take place at the Masonic Hall at 30 Pleasant Street. There is no admission fee. There are wide variety of wonderful local makers who have been working hard to make special gifts for your special someone. Come do a little holiday shopping with local artisans! We hope...

  • Skate with Santa!

    Union Arena 80 Amsden Way, Woodstock, Vermont

    Visit Union Arena during Wassail weekend for a public skate event.... with special guest! Adult (ages 13 & up) $8.00 / Youth (ages 4-12) $6.00  / Seniors (ages 60+ ) $5.00 Skate rentals available

  • Cupcakes with Santa

    31 The Green, Woodstock Town Hall Theatre 31 The Green, Woodstock Town Hall Theatre, Woodstock, VT, United States

    Come meet Santa and his elves for this family celebration! Take a picture with the big guy and share some great scrumptious cupcakes in our lobby, made by Woodstock's own...

    Free
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
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