A familiar orange-clad figure will be back and hopping around Railroad Street this weekend. Stunt comedian Wacky Chad will return as one of Berkshire Busk!’s headlining acts on both Friday, July 5, and Saturday, July 6. Festivities throughout downtown Great Barrington begin at 6:30 p.m.
Friday Highlights: High-Flying Acts, Swinging Americana
Wacky Chad has been part of Berkshire Busk! since the beginning, and his extreme pogo-stick stunts have become a treat that local audiences look forward to year after year. When not joking, dancing, and jumping down lower Railroad Street, Wacky Chad has been seen on stages including “America’s Got Talent,” “The Gong Show,” and pop-up shows across 26 different countries.

Upper Railroad street also sees a returning act in Rees Shad and The Conversations. Shad is a prolific songwriter and has put out three albums in the past three years alone: “The Galahad Blues,” “Six Strings & a Story,” and “Tattletale.” Those who are already familiar with the Americana combo are bound to hear a new song or two in this summer’s performance.
To round out the crowd-pleasing aerial acts, Chalk Gremlin Circus will be returning with their quirky and fun stunts at the First Congregational Church. Other beloved buskers like Katherine Winston, Mike Pagnani, Brian Hailes, and more can be found throughout town.
Saturday Highlights: Brass Bands, Blues, and Balloons
On Saturday night, the Berkshire Resilience Brass Band will take the stage opposite Wacky Chad! on Upper Railroad Street. Led by Shamu Sadeh, the group draws on traditions from Cuba to New Orleans for some big-band fun.

Throughout the rest of Great Barrington, the circus fun continues with the talented juggler Timbalanced and creative balloon twister Balloon Ben, who is willing to take on even the most out-of-the-box requests with his ballooning skills. Attendees can also enjoy music from three-time Boston Blues Finalist Robin OHerin, singer-songwriter Michael Aaron, fingerstyle bluegrass artist Joel Blumert, and jazz courtesy of Eric Bascom and Ted Levine.
Extended Schedule on Saturdays

Spend Saturday morning at the Great Barrington Farmers’ Market with the incomparable swinging jazz of The Lucky Five. Then pay an early visit to Balloon Ben, who will be in front of Robin’s Candy for an additional time slot of 12 p.m. to 2 p.m. before returning for the evening. The San Diego-born singer-songwriter DAYMEN will be captivating audiences at Berkshire Mountain Distillers beginning at 2 p.m.
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.