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AT BERKSHIRE BUSK!: Week of July 24, 2025

The new partnership between Berkshire High Peaks Festival and Berkshire Busk! is just one of many new acts coming to the festival on Friday and Saturday.

Berkshire High Peaks Festival, a classical music summer festival for teens, is set to collaborate with Berkshire Busk! for the first time this Saturday, July 26, starting at 6:30 p.m. The new partnership is just one of many new acts coming to the festival on Friday and Saturday.

Friday Highlights: Hack Monet, Jaane Doe, Magic, and More

Friday brings the return of Housatonic’s blues band Hack Monet, fronted by Luke Germain. The group’s show on the Warrior Trading Stage will alternate with festival newcomer Slow Pony on the Haddad Subaru Stage. Festival goers who fell in love with the Dust Bowl Faerie’s brand of “freak-folk” earlier this month will find kindred spirits in the folk-punk ensemble of Slow Pony.

Elsewhere downtown, Jaane Doe will bring her signature mix of originals and favorites from the past few decades to the Berkshire Money Management Stage. Jaane Doe was first discovered in Saratoga’s Caffe Lena at 16, and since then, she has shared stages with musical greats, produced many original albums, and even directed an award-winning short film titled “PAWNS.”

Magician Myron the Magnificent, roaming clown Ol’Miss Money Bags, blues musician Robin OHerin, and more will be busking on sidewalks and alleyways around Main Street.

Slow Pony’s accordion-driven music features a rotating cast of players every show. Photo courtesy of Berkshire Busk!

Saturday Highlights: High Peaks Festival Musicians, Brass Bands, Poetry

The Berkshire High Peaks Festival, produced by Close Encounters With Music, brings bright young classical talent from around the world to their home base on the Simon’s Rock campus. Their performance at the Berkshire Money Management Stage is just one of many shows currently taking place until the festival finishes on August 3.

Around the corner on Railroad Street, two Berkshire bands will alternate shows. Up first is the bluegrass band The Juckets, led by singer-songwriter Kevin James Healey, on the Haddad Subaru Stage. The Berkshire Resilience Brass Band—whose repertoire includes music of the African diasporas, Cuba, New Orleans, and the Balkans—will bring joy to the Warrior Trading Stage.

Busking poet Jacqueline Farrara, steel guitarist Daryl Brooke, Balloon Ben, and aerialist Lia Pearl are just a few of the other buskers to be found throughout downtown on Saturday evening.

The Juckets playing on Railroad Street in 2024. Photo by Roman Iwasiwka.

Extended Schedule on Saturdays

After his performance at Berkshire Mountain Distillers, Dav!d Reed will return to the busking festival on Aug. 1 and Aug. 23. Photo by Berkshire Busk! staff.

Folk duo John and MaryBeth Bunge, known professionally as Jasperoo, will open the morning at the Great Barrington Farmers’ Market from 10 a.m. to 12:30 p.m. Once the market concludes, kids can head to Robin’s Candy to pay a visit to John the Balloon Guy from 1 p.m. to 3 p.m. The unmissable, sunny presence of Dav!d Reed will bring his brand of blues and Americana to Berkshire Mountain Distillers from 3 p.m. to 5 p.m.

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The Edge Is Free To Read.

But Not To Produce.