Wagon Wheel

The song describes a hitchhiking journey south along the eastern coast of the United States, from New England in the northeast to the intended destination of Raleigh, North Carolina, where the protagonist hopes to see his lover. The chorus and melody for the song comes from a demo recorded by Bob Dylan during the Pat Garrett and Billy the Kid sessions with the title of "Rock Me Mama." Ketch Secor of Old Crow Medicine Show added partly autobiographical verses to Dylan's unfinished song, transforming "Rock Me Mama" into "Wagon Wheel." It was included on Old Crow Medicine Show's major label debut, O.C.M.S. in 2004 and became their most popular recording and a bluegrass standard. The song was certified gold by the Recording Industry Association of America in November 2011.

Ketcham Secor was just 17 when he wrote this song. He described it to NPR as an "autobiographical daydream that you might have in between classes, you know, if you're flunking math. Then you might decide you want to write a song about hitchhiking away from New England and going back down South where you come from."

The Bob Dylan bootleg that formed the basis for this song had an intelligible chorus ("Rock me mama...") but the verses were gibberish, so Secor re-wrote them. Dylan and Secor are the credited songwriters on the track.