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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 Green at night over head

    Wassail Artisan Market

    Friday December 12th 1-6PMSaturday December 13th 10AM-4PM Wassail Artisan MarketSponsored by The Woodstock Chamber of Commerce Local Artisan's selling their goods in the heart of the Village, located on the...

  • Wassail Weekend

    Woodstock gets into the holiday season during Wassail Weekend, a celebration of the sights, sounds, and spirit of winter. Take in the magic of twinkling light displays, decorated historic homes, and the sounds Holiday music throughout the Village. 

  • Alice by Heart Musical

    In the rubble of the London Blitz of World War II, Alice Spencer’s budding teen life is turned upside down, and she and her dear friend Alfred are forced to take shelter in an underground tube station. When the ailing Alfred is quarantined, Alice encourages him to escape with her into their cherished book and...

  • horse-drawn sleigh ride at Billings Farm

    Wassail Weekend at Billings Farm

    69 Old River Rd 69 Old River Rd, Woodstock, VT, United States

    As Woodstock celebrates its 41st annual Wassail Weekend, Billings Farm & Museum invites guests to step back in time and experience the holiday spirit of the 1890s. Visitors can explore...

  • 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 in front of TD Bank

  • Strong & Slow Flow
    Strong & Slow Yoga

    Strong & Slow Yoga

    184 Hartland Hill 184 Hartland Hill, Woodstock, VT, US

    Join us for Strong & Slow Yoga on Saturdays, 10:00am at Wise Pines - 184 Hartland Hill Road, Woodstock, VT 05091. Whether you're a beginner or an experienced yogi, this class is designed to accommodate all levels. Come and enjoy a rejuvenating session of yoga in a welcoming and inclusive community setting. Instructor Chelsey Seering...

  • 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...

  • Victorian Garland Making

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

    Kick off Wassail Weekend with a cozy, hands-on family craft event! Join us at the Woodstock Town Hall Theatre to create your own Victorian-style garlands using popcorn, cranberries, and charming decorative pieces. It’s the perfect way to spend time together, get festive, and warm up before the Wassail Parade on the Green at 2 PM. We’ll have hot mulled...

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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