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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 Village Green.

  • 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 Victorian Christmas traditions, learn about the origins of Wassail, and view the authentically decorated Historic House. Hands-on activities include candle dipping, interactive butter making, and...

  • 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...

  • 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...

  • 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 person Meet at the lawn in front of M&T Bank

  • Public Skate at Union Arena

    Public Skate at Union Arena

    Union Arena 80 Amsden Way, Woodstock, Vermont

    Public Skate sessions are open to the public and a great way to have fun with family and friends. *Schedule Subject to Change* Public Skate Rates - Adult (ages 13 & up) $8.00 / Youth (ages 4-12) $6.00  / Seniors (ages 60+ ) $5.00Child (ages 3 and under) Free / Super Senior (ages 70+) Free Skate...

    $5.00 – $8.00

  • Children’s Stories for December Holidays @ NWPL

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

    Children’s Stories for December HolidaysJoin us for a lively reading of storybooks celebrating the season. We’ll gather on the Mezzanine right after school at 3 pm and begin the stories when everyone has had a little snack and settled.December brings the Winter Solstice, Hanukkah, Christmas, and more! These short, dark days are marked with a...

  • VINS Lights
    Forest of Lights at VINS

    Forest of Lights at VINS

    VINS Nature Center 149 Natures Way, Quechee, Vermont

    Experience winter magic as thousands of lights transform the VINS Nature Center into an enchanted wonderland. Stroll through spectacular displays featuring this year’s new attractions: the Sparkle Dome, Fiery Tower, Dancing Lights Pavilion, and Under the Black Light Sea. Our captivating holiday experience expands each year with fresh exhibits and activities, creating joy for visitors...

  • Creating a pizza
    That’s Amore! Pizza and Calzone Cooking Class

    That’s Amore! Pizza and Calzone Cooking Class

    Bridgewater Corners Bridgewater Corners, Bridgewater Corners, VT, United States

    Have fun creating your own pizzas! Though award-winning Chef Ted can teach you almost anything food related, for this event he leads a hands-on pizza and calzone class. You’ll learn how to: make fresh dough make shells for later use treat toppings make sauce fashion a calzone grill a pizza, weather permitting We’ll use mostly organic and regional ingredients...

  • 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

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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