Wyatt Durette was inspired to write "Highway 20 Ride" while driving along Interstate 20 between Atlanta, Georgia and the Georgia/South Carolina state line in Augusta, Georgia to drop off his son, Wyatt IV, so that his mother could pick him up.

[1] Durette told Country Weekly magazine that, during one such trip, he began to think about "how [Wyatt IV] would perceive [him] as a father.

'"[2] Leeann Ward of Country Universe gave the song an A, referring to it as "touching and tastefully constructed" and saying that it "may turn out to be one of the best singles of 2009.

"[3] Mark Deming of Allmusic, in his review of the album, stated that the song, as well as "Free," "show the influence of the more sentimental branches of the Texas singer-songwriter tradition.

"[5] Jessica Phillips of Country Weekly magazine gave it four stars out of five, with her review calling it "honest, not syrupy" and describing Brown's "powerful vocals" as a standout.