Oregon was the last British territory in the U.S.—did the English stick around when the New Englanders took over and influence the culture? I can't see our hedonistic, Brit-like vibe coming from Yankee Puritans.
In honor of Oregon History Month (a new observance I just made up), we're going to answer a second history question from Puscifer here. Sure, he's named after a Tool side project and he submitted his question in Comic Sans, but I'm feeling generous.
First off, Pus—can I call you Pus?—you're overstating the influence of New England on our early history. While the famous coin flip that decided Portland's name happened to be contested between a Bostonian and a denizen of Portland, Maine, it's just a coincidence—the pair could as easily have been a Tennessean and a Québécois.
And while the Brits and the U.S. did share dominion over Oregon for a while (with each other, not—God forbid—with the natives), this agreement ended by 1846, and probably didn't contribute much to the preponderance of cozy pubs, Vespa scooters and poor oral hygiene the Rose City enjoys today.
If there's a cultural similarity between Cascadia and Old Blighty, I'd argue it's not history but climate that's to blame. Both Portland and, say, Liverpool enjoy (suffer might be a better word) what's called "oceanic" or "marine west coast" climate—cool summers, mild winters, minimal sunshine.
Thus, both here and in the U.K. the weather is never so bad that you can't make it to the pub, but never so good that you can do anything else. This leads to a city and/or nation of sad, damp, doughy people drinking to kill their pain—and starting a lot of bands, because we're sure as hell not gonna get laid via our sculpted abs.