Just read this whole ordeal today. I've been a fan of Dylan's for a while now, but only really closely listened to the lyrics of "Hattie" in the movie "I'm Not There". This tempted me to do some research on the subject, which naturally lead to a lot of research. It was needed, as the 60s were a loooooong time before mine.
From the song I assumed this happened decades before the song was written. It was just the sort of feeling I received from it. That's obviously not the case at all, and wasn't even aware segregation was still a "big deal" in the early 60s.

It's very impressive this thread has been going on for more than 6 years as well.