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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.

Planning ahead? See our annual events here, and check out our blog for more itineraries and things to do in Woodstock.

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Benefit/Fundraiser

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  • Apples & Crafts 2

    Apples and Crafts and Food Truck Festival

    21701 Maxham Meadow Way 21701 Maxham Meadow Way, Woodstock, VT, US

    More than 100 juried Craftspeople, Specialty food producers, and Food Trucks.Jewelry, paintings, pottery, clothing, handbags, crafts, photography, and much much more!$5 per person. Children ages 12 and under are free. Bus groups welcome. This is a dog-friendly event!Proceeds to benefit the Woodstock Rec Center.Saturday, October 12th-10:00 am-4:00 pmSunday, October 13th, 10:00 am-3:00 pm  

  • Apples and Crafts and Food Truck Festival

    21701 Maxham Meadow Way 21701 Maxham Meadow Way, Woodstock, VT, US

    More than 100 juried Craftspeople, Specialty food producers, and Food Trucks.Jewelry, paintings, pottery, clothing, handbags, crafts, photography, and much much more!$10 per person. Children ages 12 and under are free....

  • Horse-Drawn Wagon Rides

    Join us for a horse-drawn wagon ride through the middle covered bridge and around the Green in Woodstock Vt. Cost is $20 per person Saturday and Sunday. .Proceeds to benefit...

  • Trivia! | Library After Hours

    Trivia! | Library After HoursTest your knowledge! Trivia questions will run the gamut from pop culture, sports, history, and – of course – books. The winning team gets bragging rights and their picture on the coveted digital display board!A “fun-raiser” that is also a mini-fundraiser, there will be a $5 entry fee per player.  Gather...

  • An Evening with Kathryn Downs

    Join us for an artist reception celebrating Kathryn Downs,a nature-inspired artist featured at AVA Gallery.Enjoy an evening of art, conversation, and lightrefreshments, including cheese and crackers.Please RSVP by November 5th to Gaige Pequenogaige.pequeno@fourseasonssir.com | C: 603.348.1143Location: Four Seasons Sotheby’s International Realty17 1/2 Lebanon StreetHanover, New Hampshire

  • A lively, festive dancefloor scene at the Cabaret

    Holiday Cabaret 2025

    115 North Rd. 115 North Rd., Barnard, VT, US

    BarnArts Holiday Cabaret kicks off a busy December with savory and sweet treats, dancing, and music by Speak Easy Prohibition Band with Samira Evans along with BarnArts performers.Saturday, December 67-10pmBarnard Town Hall (115 North Rd., Barnard)  Tickets: $35 plus optional additional donation to BarnArts end-of-year driveIncludes nibbles & dessert bars with coffee & tea. Cash bar

  • An Enchanted Wassail Evening

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

    We invite you to embrace the holiday spirit and support the Norman Williams Public Library by joining us for an Enchanted Wassail Evening, a fundraising and fun-raising event.Lights twinkle, greenery scents the air, and piano music fills the historic, elegant building. Following centuries-old Wassail traditions, we enjoy delicious food and delightful drink with neighbors 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...

  • 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...

  • Bingo Night at NWPL

    BINGO Night! – Library After Hours

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

    Join us for fun games, laughter, & chances to win prizes. Bring your friends & support the library at this fun-raiser that is also a mini-fundraiser: $5/ Bingo card for the evening.

  • Trivia Night @ the library

    Trivia! | “Library After Hours”

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

    NWPL’s own Adrian Tans will challenge us with trivia questions that run the gamut from pop culture, sports, history, and – of course – books.

    $5
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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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