Leroy Preston Performs in Randolph

Founding member of the Grammy Award–winning western swing group Asleep at the Wheel, Leroy Preston brings a vibrant mix of swing, honky-tonk country, and jazzy blues to the stage.

A Vermont native, Preston launched his career locally before co-founding Asleep at the Wheel, touring and recording with the band to international acclaim. He later moved to Nashville, where he built a prolific songwriting career. His credits include Rosanne Cash’s #1 hit “My Baby Thinks He’s a Train”, along with top-charting songs for Asleep at the Wheel, k.d. lang, and Lee Roy Parnell.

His co-writing collaborations span Los Lobos, Marshall Crenshaw, Rosie Flores, Robert Earl Keen, and many more artists who have recorded his material. After a long hiatus, Preston has returned with new songs and a stellar lineup of musicians on The Vermont Sessions, released in November 2024.