How segregated was the Old West, especially around 1899? Yes, this is Red Dead Redemption 2 related. I'm mostly interested in how it was applied to Blacks being served by White businesses like saloons.
The colony of Vancouver Island was anti slavery and passed a law stating that any slave arriving at the colony would become a free man. Sir James Douglas, the governor of the colony was the son of a British merchant and a Caribbean Creole slave. His wife was the daughter of a Scottish fur trader and his Cree wife.
When Oregon and California introduced their Whip Laws that prohibited Negroes owning land and stated that all free Negroes living in the territories be whipped once a year the merchants of Victoria sent a delegation to California with an invitation offering them land and opportunities if they became British citizens.
Some 600 black immigrants accepted this offer and moved to the colony of Vancouver Island. There they became merchants and policemen, and organized their own firefighting brigade and even received the governors blessing to form their own militia.
I am not at home at the moment so can't give precise dates but you can find them in George and Helen Akrigg's "British Columbia Chronicles."
In these two books you will incidents where white colonists of Victoria boarded ships and released black slaves and even went to Oregon Territory to kidnap a teenaged black slave.
What I find interesting is that the white colonists of Vancouver Island were willing to fight to protect the lives of black slaves, but would not interfere with Indian slaves. There are incidents in the Akrigg's Chronicles where people mention seeing Indian slaves being beaten to death by their masters or subjected to severe punishments such as branding or amputation but did nothing. I would suppose that this is because the white colonists were vastly outnumbered by their native neighbors and were unwilling to incur their wrath.