A native of Fayetteville, North Carolina, Herring is the son of a high school English teacher and a Superior Court judge. The youngest of three brothers, he attended Terry Sanford High School in Fayetteville. Although he played saxophone in the high school band, he became known for his talent on guitar, which he had begun playing at age 13. Herring had a Telecaster guitar with a Stratocaster neck, in the same style as one of his biggest influences, Steve Morse of the Dixie Dregs. After high school he formed the Paradox, a cover band that played mostly jazz fusion and songs by the Dixie Dregs, Al Di Meola, and Chuck Mangione. The band's horn section included Wayne Rigsby and Charles Humphries on trumpet and Herring on saxophone. After graduating from high school, in 1980, Herring attended a summer session at the Berklee College of Music. In addition, he is a graduate of The Guitar Institute of Technology in Hollywood, California.
Herring was the lead guitarist for the jam band Col. Bruce Hampton and the Aquarium Rescue Unit. Formed in Atlanta in 1989, its members include Allman Brothers Band bassist Oteil Burbridge and Leftover Salmon drummer Jeff Sipe. He was invited to participate on the H.O.R.D.E. tour with Aquarium Rescue Unit in 1992 and 1993 and was offered the lead guitar job in the Allman Brothers Band after Dickey Betts was arrested after a show in Saratoga Springs, New York on July 30, 1993. Herring declined to take the position full-time. Bruce Hampton left Aquarium Rescue Unit in 1994, citing time pressure as his reason. Herring and other members continued to tour in early 1997 until drummer Jeff Sipe departed for Leftover Salmon.
In 1998 and 1999 Herring went on tour as Jazz Is Dead with bassist Alphonso Johnson, keyboardist T Lavitz, and drummer Billy Cobham. The band's albums included jazz rock versions of songs by the Grateful Dead. Herring also appeared on the album Out of the Madness by The Derek Trucks Band. He went on tour with the Allman Brothers Band in 2000, then joined Phil Lesh of the Grateful Dead in Phil Lesh and Friends.

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