This theme of the rambling man and the women who love them recurs in a lot of old songs, but usually sung from the man's perspective. Besides about a thousand old bluegrass songs, I think of Glen Campbell's "Gentle on My Mind," and perhaps also Janis' Joplin's version of Kris Kristofferson's "Bobby McGee." In both of these the freedom is touched with lament. The tone is not so hopeful and naive.
But John Prine's "Angel from Montgomery" even seems to be sung by the woman that the young girl of "Someday Soon" has become. "Well when I was a young girl, I had me a cowboy, he weren't much to look at, just a free ramblin' man . . . " The woman is still longing for freedom, still feeling tied down or restricted. Many years have passed, and she wishes she could fly away. Where once she loved a man of the rodeo, even now the rodeo represents freedom to her. "Make me a poster / of an old rodeo." It's as if she wants the world to be as enchanted as it once seemed, and the tragedy is that this cannot be. Instead of the rodeo, there's just a fly buzzing at the window, unable to escape, and for the woman a deepening ennui.
Bonnie Raitt's version is perhaps the gold standard, but I love Susan Tedeschi's interpretation as well, not least because she combines it with the rousing "Sugaree."