Jack Windsor is a songwriter, singer, and recording artist based in the Greater Cleveland area. His debut full length album, My Old Ways, is available to stream or spin on vinyl. Catch him performing solo or with his 4 piece rock n roll band at a venue near you. Jack Windsor & His Band just wrapped up recording a new full length album that will be released in fall of 2026. Check out the first single, Only a Dream (So Far) below or on any your preferred streaming sites.

Shows

September 15, 2026

Secret Songwriting Society

Hosted by The Baker’s Basement

Forest City Brewery Cleveland, OH

September 19, 2026

7:00pm-9:00pm

North Water Brewing, Kent, OH

September 20, 2026

3:30pm-4:30pm

South Russell Fall Festival, South Russell, OH

September 26, 2026

10am-12pm

Geauga Fresh Farmers Market, Chagrin Falls, OH

October 10, 2026

4pm-12am

RM Pavilion Presents: Fall Fest 2026

Featuring: Jack Windsor & His Band, Cowboy Princess Brigade, Robbing Mary, & Mary’s Lane

October 31, 2026

7:00pm-9:00pm

North Water Brewing, Kent, OH

November 13, 2026

9pm-12am

Happy Dog, Cleveland, OH

Featuring: Jack Windsor & His Band, Jim McKivier & the Starry Sky Band, & Joseph Allen Beltram