3. Poughkeepsie, NY
Poughkeepsie maximizes misery across a variety of factors — from terrible weather to oppressive property taxes, both of which were cited as reasons why this barely-a-city was included on Forbes’ list of “Most Miserable Cities.” Unless your definition of “quality time” includes idling in bumper-to-bumper traffic, keep driving past this New York town.
In January of 2014, the city received another crushing blow: a downgrade by Moody’s because of its ailing economy, according to the Hudson Valley Reporter. Meanwhile, drug use and violent crime remain problematic, according to a recent address delivered by the mayor, as reported by the Daily Freeman News.
Not a typical contender, Poughkeepsie offers high incomes, but despite the fact that residents bring home the big bucks, they have little to spend their money on: this small Hudson River Valley city offers notoriously little to do, painfully long commutes, and equally painful property taxes.
And those looking to soak in some healthy vitamin D will need to head to sunnier parts: according to Sperling’s Best Places, Poughkeepsie sees only 165 days of sun every year compared to a national average of 205. And when the Tawana Brawley incident continues to be the most newsworthy thing that’s ever happened near your town, things are looking pretty grim.
Poughkeepsie is so insignificant that most people don’t even know how to pronounce its name (it’s Po-KIP-see, for the record), nor do they care to learn.
If Poughkeepsie is known for anything at all, it’s as a punch line, thanks to Gene Hackman’s famous “Pickin’ your feet in Poughkeepsie” diatribe in “The French Connection.” We’d just as soon as pass on picking out feet in general, and would certainly avoid doing so here, but if rich, boring and gray get your pulse racing, then this may be the place for you.