Berkshire Busk! will feature a professional hula hoop performer on Friday, August 2, for the very first time! The rest of the performers for this weekend will feature a mix of folk, country, reggae musicians, and more.
Friday Highlights: Lessa Hoops, Jacob Shipley, Balloon twisting, and more
Lessa Hoops combines comedy and contortion into her hula hooping tricks. She has performed in variety shows, fairs, and other festivals including The Villages Mardi Gras Festival. Friday will be her debut on the Berkshire Busk! main stage across from SoCo.
On the other end of Railroad Street, attendees can see actor, singer, and musician Jacob Shipley. Shipley is a regular performer at Berkshire Busk! and is known for his delightful mix of covers and original music. He has already released two singles in 2024, titled “Kitchen Floor” and “Older.”

Face painting, balloon twisting, busking poets, and plenty more live music will be at your fingertips throughout the rest of downtown.
Saturday Highlights: Americana, Reggae, Circus Acts

Berkshire Busk! welcomes back Firetown Road and The Haughties for a music-filled Saturday night on Railroad Street. Firetown Road, an Americana group from Connecticut, released their full-length debut album “Here’s to This Life” earlier this year. The Haughites are a vibrant Berkshire-based reggae band that premiered at Berkshire Busk! in 2023.
While there are plenty of other outstanding musicians throughout the rest of downtown—
Quarteto de Samba and singer-songwriter Abby Lappen are just a start—Saturday night will also feature busking poet Kevin Devaney, Bowey the Clown’s balloon twisting, and Magic Brushes face painting. The juggler Timbalanced will put on his circus-themed variety show on Main Street’s sidewalks.
Extended Schedule on Saturdays
Christina Dellea will play her blend of 1960s, ’70s, and ’80s pop to start the morning at the Great Barrington Farmers’ Market. Afterwards, balloon twisting and face painting will begin outside Robin’s Candy from 12 p.m. to 2 p.m.. The unmissable David Reed will be bringing his delta blues repertoire to Berkshire Mountain Distillers for Berkshire Busk! Roadside later on in the afternoon.
Berkshire Busk! is free to attend and takes place in downtown Great Barrington every Friday and Saturday evening, from June 28 through August 31. Primary festival programming begins at 6:30 p.m. Visit the Berkshire Busk! website for the full schedule of events.