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AT BERKSHIRE BUSK!: Week of July 17, 2025

Wacky Chad's athletic brand of comedy is just one of many acts coming to Berkshire Busk! this weekend, beginning at 6:30 p.m.

The world-traveling, pogo-sticking street performer Wacky Chad returns to Great Barrington on Friday, July 18, and Saturday, July 19. His athletic brand of comedy is just one of many acts coming to Berkshire Busk! this weekend, beginning at 6:30 p.m.

Friday Highlights: Circus, Acoustic Rock, and Classical

Wacky Chad begins his weekend residency on the Warrior Trading Stage on Friday, alternating show times with Garrin Benfield at the Haddad Subaru Stage. Benfield is a prolific singer-songwriter with five full-length albums under his belt and captivates audiences with his live looping.

On the Berkshire Money Management Stage, Colby Lewis and Steve Ide come together to play the best of the ’70s. Between Lewis’ band Whitewood and Ide’s role as guitarist/vocalist in three bands (Hot Sauce, The BTUs, and The Eggmen), the duo are well versed in bringing great energy to Berkshire stages.

Elsewhere downtown, a wide range of musical acts will take over the sidewalks, including classical act Bel Canto Duo, slide guitarist Daryl Brooke, and more. John the Balloon Guy and circus-comedy act “It’s Chris” are sure to be big hits with younger audiences.

Garrin Benfield writes poignant original songs. His single “What You’re Hiding,” which pays tribute to Matthew Shephard, was used in a production of the Laramie Project. Photo by Sam Brewer.

Saturday Highlights: New York City-Style Jazz, Wacky Chad’s Finale

The Greg Glassman band will play opposite Wacky Chad on the Haddad Subaru Stage on Saturday evening. Glassman has played professionally since the age of 17 and has spent his career playing opposite jazz greats—when he is not in the Berkshires, he still plays regularly at Smalls Jazz Club in New York City.

Around the corner at the Berkshire Money Management Stage, local guitarist and singer Natalie Lewis will showcase her talents. Lewis first performed at the festival at the age of 15 and currently studies music education at the University of Vermont.

Greg Glassman has shared the stage with the likes of Clark Terry, Marcus Belgrave, Roswell Rudd, Sheila Jordan, Oliver Lake, Sherman Irby, Geri Allen, David Schnitter, and John Esposito. Photo courtesy of Berkshire Busk!

Along Main Street, attendees can find face painter Deb Carver, singer-songwriter Michael Aaron, folk artist Warren Sieme, and more. Saturdays also mark the addition of the festival’s night market, featuring local artisans and nonprofit groups. On both evenings, HUHT offers free wellness experiences by means of their mobile sauna and cold-plunge system.

Extended Schedule on Saturdays

Roger and Lenny started jamming together in 2009 and have brought their love for the Golden Oldies to farmers’ markets and beyond ever since. Photo courtesy of Berkshire Busk!

Folk duo Roger and Lenny will bring their Simon & Garfunkel-esque musicality to the Great Barrington Farmers’ Market from 10 a.m. to 12:30 p.m. Then, kids can find Balloons by Bowey and face painting by Magic Brushes at Robin’s Candy from 1 p.m. to 3 p.m..

The Acoustic Medicine Show will make their busking debut at Berkshire Mountain Distillers in Sheffield from 3 to 5 p.m. The band is a project of Hudson Valley-based singer-songwriter Joseph Tobin and is set to return to Berkshire Busk! for a performance on Railroad Street this August.


Berkshire Busk! is free to attend and takes place in downtown Great Barrington every Friday and Saturday evening, from June 27 to August 30. Primary festival programming begins at 6:30 p.m. Visit the Berkshire Busk! website for information on parking, free transportation options, and the full schedule of events.

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