"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.

"Down the Road" is a mid-tempo ballad. In it, the male narrator describes his childhood love interest — a girl who lives down the road from him. Eventually, the narrator proposes to marry her, only to find out the expectations her parents have of him.

In the second verse, the narrator is now an adult, and his daughter has a love interest who lives down the road. He then explains that he has the same expectations that the parents in the first verse had, but he will still let her go down the road.

According to Country Weekly magazine, McAnally was inspired to write the song one Christmas morning after thinking about what his two daughters' lives would be like in the future (he has since had a third).

Mac McAnally's original version is the second single from his 1990 album Simple Life, his only album for Warner Bros. Records. It debuted at number 72 on the Billboard country charts for the week of July 7, 1990, fell to number 75 a week later, and then reached its peak of number 70 on the chart week of July 21. McAnally also re-recorded this song for his 1994 album Knots, which was subsequently sent to radio as a promotional single.

McAnally's rendition also features a music video, directed by John Lloyd Miller. It features McAnally performing the song on a porch while playing electric guitar.

In 2008, Kenny Chesney covered the song on his album Lucky Old Sun. Chesney's version features guest vocals from McAnally, who sings the second verse and chorus. Unlike McAnally's original which is accompanied by electric guitar, Chesney's rendition is more acoustic in nature, featuring only accompaniment from two steel-string acoustic guitars and congas. According to McAnally, the song "was not supposed to be a duet", but he agreed to record it as a duet on Chesney's album. Chesney and McAnally were nominated for the Grammy Award for Best Country Collaboration with Vocals on December 2, 2009.

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