Raised in Baltimore in a musical family, Chestnut found his earliest foundation in gospel, which he says taught him how to connect with listeners. He studied at Baltimore’s Peabody Institute and earned a jazz composition and arranging degree from Berklee College of Music in 1985. As a sideman he backed Jon Hendricks and Betty Carter and worked with Donald Harrison and Wynton Marsalis.

He signed with Atlantic Records in 1993 and most often leads the Cyrus Chestnut Trio. His 2022 album My Father’s Hands is a tribute to his late father, who first taught him to play. His most recent album, Rhythm, Melody, and Harmony (HighNote Records, 2025), is a piano quartet recording of his original compositions.

At the Mid-Atlantic Jazz Festival, Chestnut’s blend of gospel feeling, classical training, and swinging jazz makes for an uplifting, deeply felt musical experience.