"Watching Airplanes" is a song written by Jim Beavers and Jonathan Singleton, and recorded by American country music singer Gary Allan.

The song became Allan's tenth Top 10 on the US Billboard country charts after reaching number 2 in early 2008.

"Watching Airplanes" was nominated for the 'Single Record of the Year' at the 43rd Annual Academy of Country Music Awards on May 18, 2008.

The music video for this song was shot during live concerts at Red Rocks Amphitheatre in Morrison, Colorado, the Red Dirt Roundup '07 in Fort Worth, Texas, the Nutty Brown Cafe in Austin, Texas, and in Saint George, Utah.

"Watching Airplanes" debuted at number 53 on the US Billboard Hot Country Songs chart for the week of August 4, 2007.