"'Goodnight America' is about every road trip I've ever taken, in a way," Chapin Carpenter told NPR. The song describes a journey where she discovers her affection for America and the gypsy lifestyle. "The song is about there being a real fine line between the sense of being missing and being lost. It can be a pretty wonderful thing, actually," she said.
The first verse is about a Chapin Carpenter's experience in Los Angeles when she was trying to cross a street but was still hobbled by a knee operation. She couldn't get across the street fast enough, and while she was initially irked, she realized that she was also humbled and anonymous, leaving her feeling liberated, in a way.