This song tells the story of a hitchhiking journey down the eastern coast of the United States, from New England through Virginia, with the ultimate destination of Raleigh, North Carolina, where the narrator hopes to reunite with his lover. Along the way, he encounters a trucker heading west from Philadelphia toward Tennessee. The chorus and melody originated from a Bob Dylan demo in 1973, with verses added 25 years later by Ketch Secor, who wrote them while feeling homesick for the South. It evokes a feeling of longing and the open road, driven by the hope of seeing a loved one.