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The Lineup

Week 8: August 16 & 17
Main Stage! Friday Night, August 16th: 6:30  - 10:00 PM

On Railroad Street in downtown Great Barrington.


Greg Glassman Band: Lower Railroad Street

Greg Glassman is a NYC-based trumpeter, composer, and educator. A protégé of jazz greats, Marcus Belgrave and Clark Terry, Greg is a staple of the New York City jazz scene. He has recently performed with groups led by David Schnitter, Lakecia Benjamin, Camille Thurman, Saul Rubin, Javon Jackson, Willie Jones III, and many others. His band’s multi-decade NYC residency is documented in the live recording, Greg Glassman/Stacy Dillard Quintet, LIVE AT FAT CAT. He has seen the world on tour with a diverse array of artists including Burning Spear, Oscar Perez, Roswell Rudd, The Skatalites, Oliver Lake, and 2017 MacArthur Fellowship recipient, Taylor Mac. He holds degrees in Jazz and African-American Music from Oberlin College and Queens College, and has been a faculty member at Bard College since 2011. He loves cooking, games, swimming in lakes, and residing with his family in Brooklyn, NY.

Michael Lesko & Suns: Upper Railroad Street

Indie folk / alt country from the Southern Berkshires. Michael Lesko is the cosmic crooner. He sings like a blue bird and laments like a wounded coyote howling into the void. Joining him is a formidable outfit of notorious local musicians including Sam McGarrity and Elias Scimeca on guitars, Tim Morrison on drums, and Ben Backus on bass. Their new single “No Matter” is out now! @michaelleskomusic
Friday Night, August 16th: 6:30  - 8:30 PM

All around downtown Great Barrington.


Madison and friends: Rubiner's Cheesemongers

Playing traditional folk music and fiddle tunes!

Jaane Doe: Triplex Courtyard

Jaane Doe AKA Elizabeth Berliner is loved by many fans including those attendees of Berkshire Busk. She has created a oerfect blend of melodic folk rock with a little country tinged Americana in her original tunes and covers. You may hear traces of Judy, Joan and Joni, that will always make you smile Joni

Chalk Gremlin Circus: First Congregational Church

The Chalk Gremlin Circus is a group of mildly chaotic but always entertaining circus artists!

Kristoffer Andrew Ross: Castle Street Corner

Kristoffer Andrew Ross is a folk musician and singer from Center Cambridge, NY, specializing in traditional ballads of Ireland, Scotland, Britain, and New England. He performs on fingerstyle guitar and Irish bouzouki, in addition to unaccompanied song. During his performances, he enjoys interweaving relevant stories and folk history. In addition to solo work, he directs and performs with the Men o’ War Balladeers, a vocal-harmony focused Celtic and Maritime Ballad band. He has produced two albums for the group, including their 2019 release, “Low Lie the Fields.” Kristoffer also works as a farmer and stagehand in New York’s Capitol District and Vermont. More information is available at,, or on Instagram

Berkshire Hills Chorus: First Congregational Church

The Berkshire Hills Chorus is a women's a cappella group who sing four-part barbershop harmony. For the past 50+ years, we have sung all over Berkshire County including such places as Berkshire Medical Center, the Red Lion Inn, the Linde Center at Tanglewood, the Berkshire Athenaeum, and Tanglewood-on-Parade to name a few. We sing up-tunes, ballads, showtunes, holiday songs, patriotic songs, and popular music.

Balloon Ben: Robin's Candy

Balloon Ben has been twisting and entertaining in Berkshire County and beyond for 12 years. His unique style allows him to meet almost any request. He loves a challenge, so feel free to use your imagination in your requests from this talented Airbender. Your imagination is the limit!

Sherry Steiner: Carr Hardware

Sherry Steiner offers soothing improvisational original instrumentals on either a double-neck ukulele or a dulcimer or a digital piano.
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