At age 19, Vestal moved to Texas and with his brother Curtis and Russell Moore formed the band Southern Connection, which toured the Midwest and East Coast for 3 years.
[4][5] Vestal then formed his group Livewire with mandolinist Wayne Benson, guitarist and vocalist Robert Hale, and bassist Ernie Sykes.
[6] Vestal toured Japan with an acoustic jazz ensemble, and starred in Phyllis McBride's original musical production Cowboy Cafe.
[13] Starting in 2006, Vestal recorded and toured with the Sam Bush Band along with Stephen Mougin (guitar), Todd Parks (bass), and Chris Brown (drums).
[14][15] As well as being a session player in Nashville, Vestal built Digital Underground, a recording studio where he engineers, produces, and performs on various projects.
[16] Vestal has worked with Bill Monroe, Tim O'Brien, Jim Lauderdale, Shawn Camp, Ricky Skaggs, Jerry Douglas, Tony Rice, Vassar Clements, Chris Thile, Hank Williams III, Kenny Chesney, Del McCoury, Dierks Bentley, Billy Ray Cyrus, Alan Jackson, Dolly Parton,[17] Dwight Yoakam,[18] and others.
[20] On Millennia, released in 2000, Vestal is joined by John Cowan on vocals, Reese Winans on keyboards, Pasi Leppikangas on drums, Jeff Autry and Jim Hurst on guitars, and Stuart Duncan, Kati Penn, and Rickie Simpkins on fiddle.