Songfacts®:

• Chesney explained to Billboard magazine the message behind this Scotty Emerick, Paul Overstreet and Even Stevens penned song: "'Round and Round' is very different for me, melodically and production-wise. I think everybody, whether it's your job or your love life, whatever it is, there's a certain complacency that we get, the internal voice saying it might be better somewhere else, or I'm kinda sick of what I'm doing now I might want to try this or that. This song is telling us we should enjoy the right now, enjoy the moment. I think everybody searches for that certain balance and tries to quiet those thoughts in their head that they've got to be constantly moving, need to go somewhere, do this, be with somebody else. It's like all those characters in the song. The guy that lives in the mountains wants to go to the beach and the guy on the beach wants to live in the mountains. The message of the song is you've got to enjoy the moment as much as you possible can."
• Co-writer Paul Overstreet is the father of Glee cast member Chord Overstreet, who portrays transfer student Sam Evans. Her vocals feature prominently on the cast's version of Travie McCoy's hit single "Billionaire."