"Down the Road" is a song written and recorded by American country music artist Mac McAnally. McAnally has charted with the song on two separate occasions. The first of these two versions was released as the second single from his 1990 album Simple Life, and was a minor chart single for him that year. Eighteen years later, McAnally re-recorded the song as a duet with Kenny Chesney on Chesney's 2008 album Lucky Old Sun. This rendition is also McAnally's highest charting country hit, having reached Number One in February 2009.