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The Lineup

Week 2: July 5 & 6
Main Stage! Friday Night, July 5th: 6:30  - 10:00 PM

On Railroad Street in downtown Great Barrington.


Wacky Chad: Lower Railroad Street

Experience the incredible Stunt Comedian Wacky Chad in a mind-blowing show filled with extreme pogo stick tricks and uproarious laughter, captivating the audience with interactive delights. Having dazzled audiences in 26 countries, including appearances on America's Got Talent (Twice!) and The Gong Show, Wacky Chad is also featured in an award-winning documentary chronicling his 20-year journey, created by his brother. Follow the excitement @WackyChad all links on

Rees Shad & The Conversations: Upper Railroad Street

The Conversations are a swinging Berkshire based Americana combo made up of drummer Bobby Kay (Cole Broderick, Ellen MacIlwaine), bassist Jeff Link (Robben Ford, Albert Cummings), and percussionist Carlos Valdez (Mambo Kikongo) which is led by singer/guitarist/songwriter Rees Shad to cross a wide range of genres and deliver a swinging form of Americana that is both literate, imaginatively played, and grooving! Audiences at a Conversations show enjoy a swinging evening of stories and song performed by a tight knit group of musicians who thoroughly enjoy playing and sharing their music, and as a result the audience get swept up in the joy they exude.
Friday Night, July 5th: 6:30  - 8:30 PM

All around downtown Great Barrington.


Chalk Gremlin Circus: First Congregational Church

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

Quarteto de Samba: First Congregational Church

Quarteto de Samba is a musical journey to Brazil. Taz, Sam, Henry and Jean, drives the band's mission to spread musical diversity in western mass and beyond.

Facepainting by Debora: Robin's Candy

Debora is an artist & facepainter from Hinsdale MA.

Mike Pagnani: Rubiner's Cheesemongers

Mike Pagnani is a singer and multi-instrumentalist performing traditional acoustic music. He has been entertaining, educating and busking in the Hudson Valley and Berkshires for nearly 20 years.

Katherine Winston: Triplex Courtyard

From the rolling hills of New England, Katherine Winston is a Singer/Songwriter whose music is a blend of country, folk/rock, and pop. Inspired by musical icons like Stevie Nicks, Brandi Carlile, and Dolly Parton, Katherine's powerhouse vocals and raw emotional power have captivated audiences all over the country. As an American Idol alum, Katherine has toured extensively, showcasing her soulful performances and leaving fans spellbound. Her most recent single, "Last Call," is available everywhere now and new music is coming soon.
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