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Live Music & Concerts

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.

Live Music & Concerts

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Today

  • Bookstock Market

    An array of Book Authors, Artists and Food Vendors with live music on The Green organized by the Woodstock Area Chamber of Commerce, along side Bookstock's children tent and book...

  • Lyle Brewer

    Guitarist Lyle Brewer

    Artistree Community Arts Center 2095 Pomfret Road, South Pomfret, VT, United States

    Lyle Brewer is a virtuoso guitarist whose unique sound blends jazz, classical, folk, and blues influences. An integral part of the Boston music scene for well over a decade, he’s...

    $25

  • Bookstock Market

    An array of Book Authors, Artists and Food Vendors with live music on The Green organized by the Woodstock Area Chamber of Commerce, along side Bookstock's children tent and book...

  • 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...

    Get Tickets $10.00
  • Music on the Hill

    Music on the Hill Summer Concert Series

    Music on the Hill Summer Concert Series
    Artistree Community Arts Center 2095 Pomfret Road, South Pomfret, VT, United States

    Join us every Wednesday at 6:30PM through September 9th for unforgettable evenings of live music and community. FREE! We’re thrilled to kick off Artistree’s Summer Concert Series on June 24th! Pack a picnic,...

    FREE

  • Music on the Hill

    Music on the Hill Summer Concert Series

    Music on the Hill Summer Concert Series
    Artistree Community Arts Center 2095 Pomfret Road, South Pomfret, VT, United States

    Join us every Wednesday at 6:30PM through September 9th for unforgettable evenings of live music and community. FREE! We’re thrilled to kick off Artistree’s Summer Concert Series on June 24th! Pack a picnic,...

    FREE
  • Concert attendees lounging at the East End Park during summer in Woodstock, VT.

    Music in the Park at East End

    East End Park East End Park, 217-03 Maxham Meadow Way, Woodstock, VT

    Music in the Park sponsored by Pentangle at the East End Park.  Food, beverages, and cotton candy available for purchase.

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    July 5th Fireworks

    Woodstock Union High School 100 Amsden Way, Woodstock, Vermont

    Celebrate July 4th weekend and the 250th celebration of the signing of the Declaration of Independence with fireworks at the Woodstock Union High School.  Tons of fun family-friendly activities including...

  • Music on the Hill

    Music on the Hill Summer Concert Series

    Music on the Hill Summer Concert Series
    Artistree Community Arts Center 2095 Pomfret Road, South Pomfret, VT, United States

    Join us every Wednesday at 6:30PM through September 9th for unforgettable evenings of live music and community. FREE! We’re thrilled to kick off Artistree’s Summer Concert Series on June 24th! Pack a picnic,...

    FREE
  • Concert attendees lounging at the East End Park during summer in Woodstock, VT.

    Music by the River: Mal Maiz

    Music by the River
    East End Park East End Park, 217-03 Maxham Meadow Way, Woodstock, VT

    After one of the most vibrant and well-attended seasons we’ve ever had on the river, Music By The River returns for Summer 2026—bringing community, celebration, and an eclectic lineup of artists...

  • Music on the Hill

    Music on the Hill Summer Concert Series

    Music on the Hill Summer Concert Series
    Artistree Community Arts Center 2095 Pomfret Road, South Pomfret, VT, United States

    Join us every Wednesday at 6:30PM through September 9th for unforgettable evenings of live music and community. FREE! We’re thrilled to kick off Artistree’s Summer Concert Series on June 24th! Pack a picnic,...

    FREE
Community Events

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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.

  • The Ultimate Guide to Mountain Biking in Woodstock, VT
    Casuals, pros, group riders, kids and families… get ready to shred.
    Read article

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Concert attendees lounging at the East End Park during summer in Woodstock, VT.

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