The Journey of Natty Gann (1985)
It's always satisfying to discover that a beloved movie of my youth is actually a good movie. I loved The Journey of Natty Gann when I was a teenager, mostly because of John Cusack, who was cute, of course.
He's still cute, but aside from that, this is just a good movie. Good acting, good Depression-era story that's fairly realistic, good cinematography. It's pretty serious for little kids but not too serious, especially if accompanied by some history and explanation.