Events from November 14, 2025 – September 24, 2022 › Rutland County › – Happy Vermont

Vermont Events

  • Killington Turkey Trot

    The Pickel Barrel 1741 Killington Road, Killington, VT, United States

    Join the 14th annual Killington 5K Turkey Trot to help support local organizations. Run or walk—all ages welcome! The event includes live music, drinks and raffle prizes. Fee $30/$35. Rain or shine, sleet or snow! Ad by Skida: MADE IN USA - www.skida.com -Skida is an...

  • Sip & Shop in Cuttingsville

    Wally's Corner 5444 VT Route 103, Cuttingsville, VT, United States

    Stop by Wally's Corner in Cuttingsville for a reception celebrating small businesses. Enjoy food and drinks, raffles and giveaways, plus Black Friday Deals all weekend long.

  • Holiday Auction in Brandon

    Brandon Town Hall 1 Conant Square, Brandon, VT, United States

    Don’t miss the Friends of the Brandon Free Public Library’s annual Holiday Auction. Offerings are from renowned local artists and craftspeople, local business owners and more. Doors open at noon.

  • Sap Bucket Tree Lighting in Pittsford

    Pittsford Village Farm 42 Elm Street, Pittsford, VT, United States

    Join Pittsford Village Farm for its annual Sap Bucket Tree Lighting. Enjoy cookies and cocoa, stories by Maclure Library, singing by the Lothrop Choir, special holiday guests and the lighting of the “tree.” This event is free.

  • Recurring

    Brandon Winter Village: Where Holiday Magic Meets Local Charm

    Come to downtown Brandon for a European-style Christmas Market! Imagine cozy booths and glowing tents snuggled together, holiday music, twinkling lights, spicy sausage sandwiches, hot mulled wine, handmade crafts and gifts, fresh greenery, rich cocoa, live performances, warm fires, cafe tables, rosy cheeks. On Saturdays,...

    Free
  • Recurring

    Holiday Market in Killington

    Killington Grand Hotel 228 E Mountain Rd, Killington, United States

    Gather with your family and friends at the Vermont Holiday Festival in Killington. Enjoy three days of twinkling lights, festive music, and holiday cheer. Wander through the Festival of Trees, shop the Vendor Village for unique gifts, sip hot cocoa, and visit Santa himself in this heartwarming Killington tradition. For...

  • Castleton Christmas Market

    Castleton Texaco Lot 635 Main Street, Manchester, VT, United States

    Step into your own Hallmark movie at the annual Castleton Christmas Market. Enjoy local food and gift vendors, caroling, a tree lighting in front of the town library, a holiday parade down Main Street and a visit from Santa at the firehouse. -Courtesy photo /...

  • Winter Makers Market in Poultney

    Analog Cycles 188 Main Street, Poultney, VT, United States

    Shop local this season at the second annual Winter Makers Market in Poultney. Find textiles, bags, gear, maple treats, local makers, unique gifts, cool tunes and more.

  • Holidays in Mount Holly

    Mount Holly 7 Maple Road, Mount Holly, VT, United States

    The Holidays in Mount Holly is a celebration of the season with caroling, cocoa, cider, and a visit from Sant, who arrives via fire truck. The menorah will be lit to begin the Festival of Lights commemoration.

  • Joe Samba @ Pickle Barrel Nightclub

    Pickle Barrel Nightclub 1741 Killington Road, Killington, VT, United States

    Guitar slung low, microphone turned up, and emotion overflowing, Joe Samba taps into rock ‘n’ roll spirit and reggae soul all at once. The Massachusetts-born singer, songwriter, and guitarist sonically teeters on an axis of island-inflected grooves and gritty guitar-craft balanced by his dynamic vocals....

    $18.92