Winchester has been playing music for most of his life. He's played bass in a number of cover bands, played bass and wrote bluegrass songs with Bill Price and the Country Pardners in the 90s and played guitar and wrote songs for Chicken Bone, a newgrass project during the early 2000s. Lately he's played bass and been the contributing songwriter with the Americana band, Flatland Tourists. That band was voted the 2015 Carolina's Americana Band of the Year by the Carolina Music Awards. Their debut single was ranked #15 in the Roots Music Report Top 200 Americana Singles of 2015, and the debut record was ranked number 62 in the Roots Music Report Top 200 Americana Albums of 2015.
Winchester's current solo project is a blend of new original tunes all derived from works of literature combined with spoken word pieces backed by music (think: a comnbinattion of Pete Seeger or Hayes Carll with Tom Waits or Minton Sparks).
Winchester also offers writing workshops for both fiction and songs.