Near as I can tell, the first serious transportation segregation fight occurred shortly after the first railroad opened for business in New England in 1835.
Seems the free blacks in the area wanted to not have to walk around horse shit -- the actual stuff, not a metaphor for pro-slavery whites -- and were willing to pay, only the whites in the area wanted to beat the metaphorical tar out of them for daring to try.
... an appreciable number of the despised race demanded transportation. Scenes of riot and violence took place, and in the then existing state of opinion, it seemed to me that the difficulty could best be met by assigning a special car to our colored citizens.
By the way -- use this as party trivia the next time you're around smart people! -- "scenes of riot and violence" apparently used to be a not-uncommon saying. How did I come to know that? Simple: See how that source text can't be copied and pasted? I didn't want to have to type all of that, so I typed a little and searched for it. Guess which phrase I chose.
So anyway, the birth of modern mass transportation was followed shortly by the birth of the minority behaving itself and the majority rioting.
In a move worthy of 19th century white people, who had previously ruined voting rights for blacks and women in the early 19th century, those same white people ruined peaceful, horseshit-free transportation for blacks.
But things were about to get better, sort of, in places, before they got a lot better, before they got far worse, before they got better bit by bit until they were better than they had been. Today, for example, the biggest segregation issue in public transportation is everyone trying to avoid sitting next to the person who insists on starting unsolicited conversations with people who suddenly realize something very interesting is in the opposite direction.
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