"Down the Road" is a song written and recorded by American country music artist Mac McAnally.

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).

[2] Chesney and McAnally were nominated for the Grammy Award for Best Country Collaboration with Vocals on December 2, 2009.

Critic Jim Malec said that the song "provid[ed] him a comfortable pocket from which he can weave a tale" and added, "'Down The Road' brings together the best of Chesney with the best of McAnally, a songwriter whose greatest strength is his ability to breath [sic] life into characters that seem unquestionably real, and which help us discuss life’s essential and often bittersweet truths."

[7] Jacob Crogie of 411 Mania gave the Chesney version a four-out-of-five rating, saying "This re-recording is a classic example of good country!

McAnally's writing provides solid, believable, sympathetic characters which allows the listener to connect to the song emotionally.

It is McAnally's second Top 40 country chart entry, eighteen years after his previous one, the number 14 "Back Where I Come From" in 1990.