Trail Five is the latest installment in Jimmy LaFave's Trail series of previosly unreleased, live bootleg recordings.

Jimmy LaFave (born July 12, 1955) is an American singer-songwriter and folk musician born in Wills Point, Texas. After moving to Stillwater, Oklahoma, LaFave crafted a musical style called Red Dirt music and became a disciple of the state's most famous folk musician: Woody Guthrie. LaFave is an Advisory Board member and regular performer at the annual Woody Guthrie Folk Festival. In 1996 he received the Kerrville Folk Festival songwriter of the year award and appeared on the TV show Austin City Limits. He has recorded 15 albums and his 2007 release, Cimarron Manifesto, reached the No. 1 mark on the Americana Music Association album chart. In 2012, LaFave released the studio album Depending On The Distance.