How could Cascadia come into existence?

Almost impossible after 1900, when the borders and cities were already somewhat established between the US and Canada.

You'd have a way better chance of it happening before 1840 with the Columbia District/Oregon Country, though the borders would be far more encompassing than shown on your map.
 
Literally getting the borders of the Cascadia bioregion would most likely require some sort of "triumph of bioregionalism" wherein North America peacefully splits itself up. Unfortunately, in most situations the political situation at the time will determine borders.

One early idea would be to have Thomas Jefferson's idea of a United States of Pacifica, allied with the United States of America, become more popular. But I don't truly understand who's going to set that state up, because anyone who did would be coming from America, and I don't know why they'd necessarily

I suspect that after 1900 one would need some pretty drastic changes to have Cascadia come into existence. As it is, today you will hardly find any people in Cascadia who identify as Cascadians; I imagine most would say they are American or Canadian, with of course a Native American minority. So, you'd need some unifying cause that would 1. Start a flowering of the Cascadian identity (as opposed to American and Canadian) and 2. Cause those same people to have Quebec-like ambitions of secession.

In all reality, aside from some major disaster (most likely a war, whether civil or otherwise) affecting the United States I don't see there being much chance after 1900. Washington and Oregon have too many ties to America, and after WWI there was much more of a Canadian national identity going on.

I think that the ideal time would be when the US and UK were still arguing over the Oregon territory. White settlers from both sides would come together and decide to be an independent country, and personally I'd like to see alliances with the tribes of the area. However, this would be unlikely given the sometimes racist nature of the settlers. Anyway, it wouldn't really be Cascadia that we would recognize because it would have a tiny population and likely neither the US nor UK would recognize it.

There was a great Cascadia thread... years ago now, that went on for pages and involved an entire theoretical government (featuring three presidents working together) and constitution. Should try to find that...
 
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