Events in Bennington today

● Listings verified — Friday, September 25 · every listing checked against its source by our Bennington editors

Today — Friday, September 25

3 events today. See what the weekend holds →

  • 9am

    Fall Into Ranch

    69 Stillwater Bridge Rd, Schaghticoke · verified Sep 20
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    Over two days, ARHA judge and multi-breed carded judge Joan Werner leads focused training to help riders excel in the ranch horse show pen. A multiple-time world champion trainer and rider, she shares a judge’s-eye view of ranch classes, highlighting what matters most in the pen. Sessions include individual cattle work as well as dry work to build fundamentals and polish.

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  • 6pm

    Common Craft Night

    165 E Main St, North Adams · verified Sep 20
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    Enjoy a relaxed creative meetup for locals and visitors to work on personal projects alongside community-minded makers with a playful spirit. Bring any portable activity you love, such as knitting, crochet, embroidery, painting, drawing, writing, hand spinning, chain maille, coloring, diamond painting, or even Legos, and create in good company. The environment is welcoming to everyone and LGBTQ+ friendly. No registration is required, and no Common Folk membership is needed.

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  • 8pm

    Madison Cunningham: Ace Tour

    B11.2 Swing Space, 1040 Mass Moca Way, North Adams · verified Sep 20
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    Grammy-winning singer and songwriter Madison Cunningham brings a folk-centered performance to the Hunter Center to celebrate her newest album, Ace. The record treats heartbreak as both an ending and a doorway to possibility, tracing a path from falling out of love through loss and toward love again. It is her third release on Verve Forecast, a fourteen track collection co-produced with Robbie Lackritz, known for work with Feist, Rilo Kiley, Bahamas, and Peach Pit. Building on the momentum of Revealer from 2022, which earned her the Grammy for Best Folk Album, Ace moves from observational writing to feeling-first songs after a period of writer’s block and places piano at the forefront for a sweeping, peak-like sound. Its first single, My Full Name, drew praise from PASTE for lyrics that feel expansive and intimate, with a timeless poetic quality.

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Coming up this week

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Saturday, September 26 3 events
  • 9am

    Makers on Main - Weekly Craft and Artisan Market

    Main St, North Adams, MA 01247, United States, 55 Main St, North Adams · verified Sep 20
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    This market offers a welcoming space that brings creative work out of the studio and into public view. Emerging artists and experienced makers present their work, try out new ideas, and grow passion projects in a professional environment that supports participation in the local economy. Visitors can meet creators, discover works in progress, and experience a community-minded marketplace. Vendor opportunities are available for those interested in participating.

    Event website ↗
  • 9am

    2026 Summer Farmer's Market

    Main St., North Adams, MA, United States, Massachusetts 01247, 55 Main St, North Adams · verified Sep 20
    Free

    Explore local produce alongside baked goods, sweet treats, and handmade items at this community market. It takes place every Saturday and continues regardless of the weather.

    Event website ↗
  • 11am

    SoberFest 2026

    601 Main St, Bennington · verified Sep 20
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    A block party centers around Turning Point Recovery Center of Bennington, featuring live music, vendors, and the return of both a wellness village and a kids village. Guests can also tour the center’s relatively new home. Dedicated to cultivating a community that embraces a substance and alcohol-free lifestyle, the event highlights life in recovery.

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Monday, September 28 1 event
  • 5pm

    Common Folk Writer's Jam

    Common Folk, 165 E Main St, North Adams · verified Sep 20
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    Common Folk Writer's Jam offers a welcoming place to push through creative roadblocks and exchange ideas with fellow writers. Poetry, prose, and everything in between are welcome. Ask for feedback, try prompts for inspiration, brainstorm together, or simply settle in to write alongside others in a calm, supportive setting. Please bring a notebook and pencil or a device for writing. Open to members and nonmembers.

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Tuesday, September 29 1 event
  • 6pm

    Grief Support Group

    66 School St, Williamstown · verified Sep 20
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    This adult, peer-led grief support group offers a compassionate space for conversation and mutual support. Gatherings take place at the Youth Center building, with open discussions guided by participants. For more information, call the Youth Center at (413) 458-5925.

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Thursday, October 1 2 events
  • 10am

    North Adams Draws

    Common Folk Artist Collective, 165 E Main St, North Adams · verified Sep 20
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    An uninstructed, drop-in portrait drawing studio invites artists of all experience levels, from first-timers to seasoned professionals, to practice likeness, proportion, and dramatic light in a relaxed, self-directed setting. There is no teaching or critique, so participants can focus on developing their personal style at their own pace. A single model maintains one portrait pose for the entire session, organized into 20-minute drawing intervals with short stretch breaks, plus a longer 10 to 15 minute pause midway. Please bring your own materials and paper. Supplies that work well include graphite, charcoal, conté, colored pencils, ballpoint pens, and clean, non-messy sketchbooks. Oil painting is not permitted at this time while ventilation and disposal solutions are addressed, with the goal of allowing oils in the future. This is a pay-what-you-can session. Contributions support model fees and help sustain the space. RSVP by emailing NorthAdamsDraws@gmail.com.

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  • 4pm

    Playful by Nature - Play & Learn Group

    The Family Center, 210 State St, North Adams · verified Sep 20
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    Explore nature together in a registered play and learn group built around the Boston Children's Museum Nature curriculum. Designed with young children in mind, it is especially suited for ages 2 to 4. Each participating family receives a take-home kit to support hands-on discovery. This series runs for six weeks. Registration is required. To sign up, call 413-664-4821.

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