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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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Events

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 

  • Chef shows woman how to make a tortellini pasta

    Rid Your Pasta Performance Complex, Cooking Class

    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, humor, and a large repertoire of songs that were influenced by the Great American Song Book. They have performed all over the world and have...

  • 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 Artistree's "Holiday Music in the Hayloft". Enjoy timeless holiday favorites and jazzy renditions of seasonal classics performed by professional local musicians in an intimate cabaret setting....

  • 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

  • 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

    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 Splendid Bakes.

    Free
  • Woman carrying a pan of small soufflés just out of the open oven

    The Soufflé Also Rises and Apples in Pastry, Cooking Class

    The Soufflé Also Rises and Apples in Pastry, Cooking Class
    Bridgewater Corners Bridgewater Corners, Bridgewater Corners, VT, United States

    Having owned a restaurant named Hemingway's, we couldn't resist the title. Because we love cooking parties this is just one of many you can have here at our mountain-top retreat. Though Chef Ted can teach almost anything food-related, for this event you'll learn hands-on the secrets to making a delicious soufflé and more. First, we handle...

  • 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 and 3:00 PM on Sunday, December 14, 2026, to make your own holiday door swag using natural materials gathered from the King Farm property. Staff...

  • 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 at 4:00 PM  Doors open at 3:30pm Space is limited so Reserve your tickets today: This is for the entire community, therefore the event tickets are...

    Free
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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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