"Carefree Highway" is a song written by Gordon Lightfoot and was the second single release from his 1974 album, Sundown.

He was driving from Flagstaff to Phoenix and saw a sign with those words pointing to the town of Carefree.

"[2] The song employs "Carefree Highway" as a metaphor for the state of mind where the singer seeks escape from his ruminations over a long ago failed affair with a woman named Ann.

"[3] The song, however, is addressed to a personified "carefree highway," the highway to which the "old flame" mentioned in the song refers, which the singer has "got to see," and when he says, "I wonder if the years have closed her mind," he is wondering not about Ann, whom he can scarcely remember, but whether he is still capable of feeling the same elation he used to experience on the road — the road on which he now wants to "slip away."

When the singer says "I guess it must be wanderlust or tryin' to get free," he is trying to explain to himself the attraction of the solitary nomadic life that used to give him, ironically, a "good old faithful feelin'."