Live music in Catskills, NY

● Listings verifiedMonday, September 21 · every listing checked against its source by our Catskills editors

Live music this week

9 shows across Catskills this week. All events →

Tuesday, September 22 2 shows
  • 11am

    Rhett Miller's Songwriting is Magic Retreat

    Music Masters Collective, 12 Valley View Rd, Big Indian
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    Rhett hosts a creative retreat in Upstate New York for working and aspiring songwriters, along with fans who want a behind the scenes look at how songs come to life. The program features workshops, seminars, open mics, group meals, and intimate performances by Rhett and special guests as they share songs and talk through their creative process. A limited number of participants can present original work in the "What's Great / What If" session and receive direct feedback from Rhett and the guests. All activities are held at Full Moon Resort. Lodging is on site and air conditioned, ranging from cozy bed and breakfast style rooms to premium cottages with mountain view private decks, Smart TVs, and elegant bathrooms. Deluxe and standard lodges are available for different budgets, and there are fully equipped glamping tents and other camping options. Accommodations are a short walk from daily sessions. When not in class, relax by the swimming pool, follow the paths along the Esopus Creek, and explore the Catskills on nearby hiking trails. Registration is limited to encourage meaningful connection and give each participant time to engage directly with Rhett and the community.

    Event website ↗
  • 8pm

    Madison Cunningham

    Bearsville Theater, 291 Tinker St, Woodstock
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    Madison Cunningham appears at Bearsville Theater in Woodstock, New York as part of her Ace Tour.

    Event website ↗
Wednesday, September 23 2 shows
  • 3pm

    Woodstock Farmers Market

    Rock City Rd, Mountainview Ave Lot, Woodstock, NY, 12498, NY
    Free

    Browse a lively mix of local vendors at the Woodstock Farmers Market. Enjoy live music while you shop, and pick up fresh, handmade dog treats.

    Event website ↗
  • 8pm

    The Wailers

    Bearsville Theater, 291 Tinker St, Woodstock
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    The Wailers perform at Bearsville Theater in Woodstock, NY in a milestone concert honoring five decades of music. The evening celebrates the band’s enduring legacy with a set highlighting songs from throughout the years.

    Event website ↗
Thursday, September 24 2 shows
  • 7pm

    Bruce Katz Band

    Colony, 22 CR-33, Woodstock
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    Colony Woodstock NY hosts the Bruce Katz Band, led by pianist and Hammond organist Bruce Katz. A 30 year veteran, Katz has released 12 albums as a bandleader and has appeared on more than 85 recordings by other artists. His collaborations include Ronnie Earl, John Hammond, Delbert McClinton, Gregg Allman, Duke Robillard, Little Milton, Maria Muldaur, Jimmy Witherspoon, Paul Rishell, Mighty Sam McClain, Debbie Davies, and David "Fathead" Newman. He is a ten time Blues Music Award nominee for Piano Player of the Year, including 2025. He received the Blues Music Award for Best Acoustic Album for Journeys To The Heart Of The Blues with Joe Louis Walker and Giles Robson, and earned a 2020 nomination for Acoustic Album of the Year for his solo piano release Solo Ride. The band has toured widely, with recent trips to Switzerland, Denmark, Germany, Romania, the Czech Republic, Poland, and the UK, and additional European dates this fall. The lineup features Aaron Lieberman of God Street Wine on guitar and vocals, John Medeiros Jr of Joe Louis Walker on drums and vocals, and Bruce Katz on piano and organ.

    Event website ↗
  • 8pm

    Sean Hayes

    Bearsville Theater, 291 Tinker St, Woodstock
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    San Francisco Bay Area songwriter Sean Hayes brings a mix of folk, soul, and R&B influences to the Bearsville Theater Lounge in Woodstock, joined by Etienne de Rocher of Haunted Shed. His songs pair a husky, expressive voice with roots-driven grooves, blending close-to-the-heart storytelling with rhythms that invite movement.

    Event website ↗
Friday, September 25 2 shows
  • 7pm

    The Music of Mamma Mia!

    The Byrdcliffe Barn, Woodstock
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    Rock Academy students bring the music of Mamma Mia to Woodstock in a lively performance. Young musicians ages 8 to 18, from beginners to advanced, take the stage as part of the school’s summer season. Tickets are available from Rock Academy students or at the door, depending on availability. Rock Academy is a year-round music school in the Hudson Valley, recognized as Chronogrammies Best Music School for six consecutive years, dedicated to teaching kids and getting them on stage to perform.

    Event website ↗
  • 8pm

    Katie Pruitt

    Levon Helm Studios, 160 Plochman Ln, Woodstock · verified Sep 18
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    Katie Pruitt brings the Fools for the Fleeting Tour to Levon Helm Studios in Woodstock, NY, highlighting the warm, soulful vocals and frank storytelling that have defined her rise. In less than ten years, the singer, songwriter, and guitarist from Georgia, now based in Nashville, has become a resonant voice for navigating modern life with honesty and heart. Her 2020 debut album Expectations drew wide acclaim and earned her a nod from the Americana Music Association in the Emerging Artist of the Year category, setting the stage for a body of work that tackles identity, self-acceptance, and the courage it takes to live truthfully. Her latest release, Fools for the Fleeting, picks up that thread by looking squarely at impermanence. The album reflects on environmental unease, the delicate nature of love, and the loneliness intensified by a screen-saturated world. Musically, it leans into an earthy mix of Americana and indie rock shaped by acoustic textures and an in-the-room feel. Across its ten tracks, and following 2024’s Mantras, the record treats the natural world as a lens for inner reflection and reaches further outward in scope and insight. Studio collaborators on the project include guitarist Juan Solorzano, associated with Ruston Kelly and Parker Millsap, and drummer Aksel Coe, known for work with Ella Langley and Sierra Ferrell. The tour centers on these songs and themes, offering a performance focused on change, grief, connection, and the steadying clarity that comes from presence and release.

    Event website ↗
Saturday, September 26 1 show
  • 6pm

    The MacS Band

    Chicken Run, 5639 State Route 23, Windham
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    The MacS Band brings a live show to Chicken Run.

    Event website ↗

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