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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.

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

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Today

  • Wassail Weekend luminaries

    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 

  • 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...

  • 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 personMeet...

  • 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...

  • 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

  • Swag Making at King Farm

    Wreath Making Join Vermont Land Trust and WoodstockUnion High School’s CRAFT Program for a festive afternoon of creativity at King Farm in Woodstock.     Drop in anytime between 1:00...

  • The Messiah – Sing-Along

    7 South Street 7 South Street, Woodstock, VT, United States

    “The Messiah” – Presented at Our Lady of the Snows Church, featuring professional musicians and local talent. Come join in on this family tradition for over 50 years. Lobby opens...

    Free
  • Small Works
    Small Works Gallery Exhibit

    Artistree Small Works Gallery Exhibit

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

    Small Works: An annual holiday exhibit featuring artworks and fine crafts that celebrate the season. Opening Reception: Friday, November 14th from 5:30-7:30pm The Small Works exhibit features size-restricted 2-D and 3-D artwork  and fine crafts by area local artists. Paintings and prints 144 square inches (12"x12") or smaller will be displayed for your holiday viewing (and...

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.

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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