Lightfoot got the idea for this song from a road sign he saw just north of Phoenix, Arizona. The Carefree Highway intersects I-17, and leads to Carefree, Arizona, a small community north of Phoenix.
In the April 1975 Crawdaddy magazine, Lightfoot explained: "I thought it would make a good title for a song. I wrote it down, put it in my suitcase and it stayed there for eight months."
The woman in the song was Lightfoot's girlfriend when he was 22. Her name was Ann.
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