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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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Today

  • Wassail Weekend: Holiday Ornament Making for Families

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

    Celebrate the magic of Wassail Weekend with a joyful, hands-on workshop for all ages! ?✨ Create your own collection of whimsical holiday ornaments at a variety of festive art stations—work solo or team up with family and friends to craft one-of-a-kind decorations that will sparkle on your tree or make heartfelt handmade gifts. This merry...

  • Wassail Cafe

    Wassail Beverages on the Green! Come quench your thirst with our festival holiday drink (adult & non). $$ Card or Cash 

  • A number of rare books are arranged on a table
    Rare & Vintage Book Sale

    Rare & Vintage Book Sale

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

    Wassail Rare & Vintage Book Sale Just in time for the holidays, Norman Williams Public Library is offering an intriguing collection of rare and vintage books — a special two-day event in addition to the ongoing book sale in the foyer. From signed, century-old gems to rare classics; illustrated children’s books to ornate, pocket-sized collections...

  • 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...

  • 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...

  • Ham Gillett with a copy of A Child's Christmas in Wales

    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...

  • Ham Gillett with a copy of A Child's Christmas in Wales

    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...

  • 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 following the Horse & Carriage Parade around the Green.  Wrensong is an a cappella choral group from Vermont’s Upper Valley that focuses on the vocal...

  • 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 

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
    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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