Size: 31.3 square miles
History: I find it kind of refreshing that Fairfield readily acknowledges the natives who lived in it for thousands of years before whities showed up. The website says, “Fairfield’s coastal geography and plentiful natural resources attracted humans for thousands of years before European settlers stumbled upon the ‘fair fields’ that Native Americans called Uncoway.”
In something called “The Great Swamp Fight” a bunch of murderous Englishmen–who no surely resembled the PrissyBitch–hunted down the Pequots who had fled an earlier massacre in Mystic somewhere it what is now Southport (part of Fairfield). You know where this is going…and it doesn’t end well for the Pequots.
While what remains of the Pequots eventually got a casino, the whities got Fairfield which is now a haven for WASPs with nice houses.
Something Weird: Bigfoot made an appearance in Fairfield back in 2009. Turned out it was just a dumb kid, but The CuT was on that story like white on rice. And while The Official Preppy Handbook considers it one of the preppiest places in America, Fairfield fancies itself the “dogwood capitol of the world” (which is probably true when you consider how much landscapers love dogwoods and how many landscapers tend lawns in Fairfield).