“Travelin’ This Lonesome Road” is a Bill Monroe composition, recorded by Monroe and his Blue Grass Boys for Columbia on 22 October 1949 at Castle Studios in Nashville. Mac Wiseman sang the lead and played guitar, with Monroe singing tenor and playing mandolin, Rudy Lyle on banjo, Chubby Wise on fiddle and Jack Thompson on bass. It was the B-side of “Can’t You Hear Me Callin’,” released on 13 March 1950, from the same session.
The song is a leaving song told by a man alone on the road. He hates to go, the wind and storm are rising and the night is cold, and his thoughts turn back to a sweetheart who had once promised to be his and then left him. He sees that her love has cooled, says he will search ten thousand miles to find her, and closes each verse by asking why she left him to travel this lonesome road, growing old and still missing her.