Bearsville Bluegrass Festival Rescheduled to Saturday May 30th

The annual Bearsville Bluegrass Festival has been rescheduled to Saturday May 30th from 12-6pm at Bearsville Center, Tinker Street in Woodstock.

The organizers report this decision was not made lightly, given the expected weather conditions, postponing the event was the only way to safely and properly deliver the experience everyone expects and deserves.

If you have already purchased tickets, you will be contacted directly. Existing tickets remain fully valid for the new date, and no action is required. Your current digital or physical ticket will automatically grant you entry on Saturday, May 30th.

All scheduled artists and vendors have been in touch in order to retain the full festival program, and tickets are still available for the new festival date: CLICK HERE

Held each year over Memorial Day weekend, the festival transforms Bearsville Park into a community gathering centered around traditional bluegrass and roots music. The 2026 edition features a lineup featuring regional performers and interactive programming throughout the grounds.

The revised lineup is as follows:

11:30am Community Harmony Singing Session with Austin Scelzo

Start the day together with a relaxed and uplifting harmony workshop led by Austin Scelzo. Whether you sing in a choir or simply love music, everyone is welcome to join this joyful community session.

12:00pm Bugs on a Log with Austin Scelzo

One of the Hudson Valley’s most exciting emerging string bands, Bugs on a Log blends bluegrass spirit, warmth, and infectious energy into a live show that perfectly captures the heart of Bearsville.

2:00pm Andrea Maddox and the Hey Y’alls

We’re incredibly excited to welcome Andrea Maddox and her all-star Americana band to this year’s festival. Andrea Maddox and the Hey Y’alls is a six piece, female fronted honky tonk band living and playing in the Hudson Valley of Upstate New York.

Andrea’s Tennessee upbringing comes through her songs as she channels the legendary women of classic country music while connecting to her audiences with the timeless themes of love and heartbreak. With plenty of tunes for two-stepping and waltzing, The Hey Y’alls bring a lively dance vibe to the party. The Hey Y’alls have been featured at the O+ Festival, the Ashokan Center, Skinny Dennis Brooklyn, Daisy Dukes NYC, The Colony Woodstock, Tubby’s and many other venues in and around New York.

4:00pm Too Blue

Closing out the day is nationally acclaimed bluegrass group Too Blue. Traveling freely between bluegrass, swing & jazz, a Too Blue performance is a dynamic dose of serious fun. Smooth harmonies and adventurous musicianship bring stellar arrangements to life, and leave the listener anything but “blue”. Seamlessly blending their vocals are guitarist Betsy Rome and banjoist Joan Harrison. Mandolin powerhouse Michael Sassano and fiddler/ mandolinist David Chernack weave their melodies, while bassist Jamie Doris brings a jazzy vibe. Together, Too Blue makes exciting bluegrass that swings and entertains.

Plus Throughout the Day

  • Phoenicia Flea marketplace throughout the park
  • Delicious festival food & drinks
  • Rock & Roll Tours with Larry Germack
  • Family-friendly games and open space
  • VIP Pagodas available for groups

And best of all, advance tickets are still available for the new date.

Buy in advance and save $5 before day-of pricing increases. Get your tickets here.

Read more on Bearsville here.

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