“A Lonesome Road to Travel” was written by Joe Stuart (Joe Earl Stuart Jr., born in Knoxville, Tennessee, on 7 February 1928), a sideman who played with Bill Monroe on and off from 1955 to 1973. Stuart was the only Blue Grass Boy to record on four different instruments, over 22 recording sessions. Monroe and the Blue Grass Boys recorded his song at Bradley Film & Recording in Nashville on 15 December 1957, with Monroe on mandolin and lead vocal, Douglas Kershaw on guitar, Jimmy Elrod on banjo, Kenny Baker and Stuart on fiddles and Bessie Lee Mauldin on bass. Decca released it on the LP Knee Deep in Bluegrass on 23 June 1958.
The lyric is a man’s regret. He said goodbye to his home and set out down life’s road to find his fortune, leaving behind a true love who begged him not to go; his foolish pride made the decision. Now he has seen more than he wanted, has known little but sorrow along the way, and would give it all up to get off the lonesome road. He has gone too far to turn back, but says that if she takes him back he will settle down.
Stuart recorded the song himself on his 1975 Atteiram album Sittin’ on Top of the World, with Jake Landers on guitar, Rual Yarborough on banjo and James Whitten on bass. Later bluegrass recordings include the Bluegrass Idles’ The All-Night Gang (Rebel, 1991), Big Country Bluegrass’s Up in the High Country (Hay Holler, 1998) and Appalachian Road Show’s Jubilation (Billy Blue, October 2022).