Past Events from September 24, 2022 – November 8, 2025 › Windsor County › – Page 2 – Happy Vermont

Vermont Events

  • Ludlow Harvest Fair

    Ludlow Harvest Fair 45 Main Street, Ludlow, VT, United States

    Celebrate Vermont's fall foliage season at the 41st annual Ludlow Harvest Fair. The event will include food trucks, more than 45 vendors, games and more.   The event helps to support the Ludlow Elementary PTG.

  • Reading Fall Festival

    Reading Fall Festival Route 106, Reading, VT, United States

    The Reading Fall Festival in Felchville features a bike parade at 11 a.m., food vendors, live music, a Ducky Derby, local organization information tables, a library book sale, pumpkin painting at the Reading Greenhouse, and more.

  • Okemo Valley Oktoberfest in Ludlow

    Off The Rails 64 Pond Street, Ludlow, VT, United States

    Okemo Valley TV and Off the Rails invite you to its inaugural Okemo Valley Oktoberfest in Ludlow. Enjoy live music, craft beer, food and games. This family-friendly event is a fundraiser to benefit Okemo Valley TV.

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    Harvest Celebration in Woodstock

    Billings Farm & Museum 69 Old River Road, Woodstock, VT, United States

    Embrace the best of fall at the Harvest Celebration at Billings Farm & Museum in Woodstock. Enjoy scenic wagon rides, hand pressed cider-making, pumpkin bowling, sunflower seed harvesting, apple tasting, creative card making and more.

  • Vermont Apple Festival and Craft Show in Springfield

    Riverside Middle School 13 Fairground Road, Springfield, VT, United States

    Celebrate fall at the annual Vermont Apple Festival and Craft Show in Springfield. The event features craft and food vendors, kids activities, apples and much more.

  • Ludlow Rotary Club Chili Cook Off

    Ludlow Chili Cook Off Main and Depot Streets, Ludlow, VT, United States

    The 34th annual Ludlow Rotary Club Chili Cook Off is a chance to sample unique and delicious chili recipes submitted by local chefs and at-home cooks. Vote for your favorite! Admission $15 per person; kids under 12 $10. Price includes chili, bread, ice cream and...

  • Vermont Food & Music Festival at Mount Ascutney

    Ascutney Outdoors 449 Ski Tow Road, Brownsville, VT, United States

    Join the Brownsville Butcher & Pantry in partnership with Ascutney Outdoors to celebrate Vermont’s food, music, and community at the Vermont Food & Music Festival. The event features a full day of live music, local flavors, and craft beverages in a beautiful mountain setting. This...

  • Reggie Harris Performs at Chester Town Hall

    Chester Town Hall 556 Elm St., Chester, VT, United States

    Upstairs at Town Hall presents a performance by iconic folk singer, historian, educator and civil rights activist Reggie Harris. As a descendant of an enslaved Black woman and a Confederate general, Harris has embraced his unique heritage to create profound and beautiful music about diverse...

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    The Woodlife Carving Festival

    The WoodLife Carving Festival 1126 VT Route 103N, Chester, VT, United States

    Get ready for two unforgettable days of artistry, skill, and the roar of chainsaws at The WoodLife Carving Festival in Chester. About a dozen talented chainsaw carvers will gather to showcase and sell their incredible one-of-a-kind creations. Festival Highlights: -Quick Carve Competitions: Watch carvers transform...

  • Fall Into Winter Celebration at Okemo

    Okemo Ski Resort 77 Okemo Ridge Road, Ludlow, VT, United States

    The Fall Into Winter Celebration at the Jackson Gore Courtyard at Okemo offers hayrides, live music, apple cider bar, Okemo BBQ, pumpkin decorating and more. Admission to the event is free, but you can purchase fall activity tickets in advance online, or the day of at...

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    Harpoon Brewery Fall Festival in Windsor

    Harpoon Brewery 336 Ruth Carney Drive, Windsor, VT, United States

    Celebrate the season at the Harpoon Brewery Fall Festival in Windsor. This two-day event showcases tasty beer, live music, local vendors and delicious food.

  • Haunted Village Theater in Barnard

    Barnard Town Hall 115 North Road, Barnard, VT, United States

    BarnArts Center for the Arts presents Haunted Village Theater in Barnard. Haunting characters will lead you from the tall grasses behind the Barnard Town Hall, along Silver Lake, and amidst the trees and lawns of the Dorothy Thompson Memorial Common to experience haunting, original tales...