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Benefit/Fundraiser

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.

Would you like to share a community event for publication on our site? Submit events here.

  • Four Seasons Sotheby’s Cold Weather Gear Drive & Food Drive

    Help Support Our Community-Cold Weather Gear & Food Needed! Starting in October, we'll collect coats and cold weather gear at our Hanover and Fairlee offices, followed by a non-perishable food...

  • 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...

  • 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...

  • 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...

  • 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! – 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! | “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
  • In Full Bloom: A Library Fundraiser

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

    After the long winter, join us in welcoming Spring at the Norman Williams Public Library! Enjoy complimentary drinks, delicious light refreshments, and piano music with neighbors and friends. Preview the...

    $75
  • BarnArts Race Around the Lake 5K/10K Fundraiser

    Silver Lake State Park 250 North Rd., Barnard, VT, United States

    "The Most Beautiful Race in Vermont!" Sunday, May 17 10:30a (10K) & 11a (5K), at Silver Lake State Park. Runners (10K & 5K) and walkers (5K) circle Silver Lake on...

    $25 – $50
  • 2026 Covered Bridges Half Marathon Pasta Supper

    Saskadena Six Ski Area 247 Stage Rd, South Pomfret, Vermont, United States

    Get energized for the Covered Bridges Half Marathon at the annual Half Marathon Pasta Supper presented by the Woodstock Area Chamber of Commerce. The annual feast at Saskadena Six ski...

Community Events

Have an upcoming event you’d like to share?

Take a few moments to tell us about your event by clicking the button here and using our Community Events Submission form. You’ll need to create an account on our site to share an event. Follow the steps on the Events Submission page to get started.


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
    Read article