A year later, Herring auditioned for a spot in the United States Military Academy band Jazz Knights playing lead alto sax. He made the move to West Point and served one enlisted tour, which turned out to be a steppingstone to the New York jazz scene.
Since first touring Europe and the United States with Lionel Hampton's big band, Herring has worked with Nat Adderley, Art Blakey and The Jazz Messengers, The Horace Silver Quintet, Jack DeJohnette's Special Edition, Larry Coryell, Cedar Walton, Freddie Hubbard, Dizzy Gillespie, The Mingus Big Band, Nancy Wilson, The Roy Hargrove Big Band, Arthur Taylor, Dr. Billy Taylor, Carla Bley, Phil Woods Sax Machine (a band augmenting Woods' regular quintet to an octet with three additional alto saxophonists). Herring has appeared as a special guest soloist with Wynton Marsalis at Lincoln Center as well as with John Faddis and The Carnegie Hall Big Band. Herring now plays with the Cannonball Legacy Band, which plays in jazz festivals an jazz clubs. Occasionally, the band will play in smaller towns. Recently the band played in Bellingham, Washington at a benefit concert for the Bellingham Youth Jazz Band, a band for children and teenagers grades 6-12.
Herring has taken bands to Japan and Europe on several occasions and has appeared in nearly every major jazz festival in the world. He is also involved in jazz education, giving clinics throughout Europe and the United States. Herring has recorded 15 CDs as a leader and over 200 as a sideman.