But Portland’s weirdness is hard-won. The place was settled by pioneers who had the guts and grit to schlep across the country and then ford rapids to traverse the Cascade Range. More recent factors contributing to the city’s popularity with independent spirits—and its lack of appeal for more typical American hustlers who might have provided a countervailing force—include economic stagnation that set in after the collapse of the region’s timber industry; redlining and other manifestations of racial discrimination that persisted into the 1990s; and lush soil and unrelenting rain (a boon for local produce of both the edible and smokable varieties).
Hippies, hipsters, homosexuals and other deviants moved to town in waves until weird started to look normal. Consequently, those who wanted to keep defining themselves as weird had to worry about being more alternative than the Joneses—which explains people like Dingo Dizmal, a thirtysomething clown of my acquaintance who rode around on a tall bike made of two frames fused together while rocking a top hat.
At the same time, the generally lousy economy meant that, like kids in a poor neighborhood bouncing on an old mattress, Portlanders had to make their own fun. Hence the thrift store industrial complex that keeps ’80s blouses circulating until they fall apart or get made into pillows; the competitive sport of coffee connoisseurship; and the Sunday tradition of midnight “zoobombing,” in which participants unlock a fleet of kids’ bikes piled high around a bike rack downtown and head west to the top of an 800-foot hill at the Oregon Zoo.
Brooklynites seeking a vision of the future need only visit Portland’s Casa Diablo, which claims to be the nation’s first vegan strip club, then pop into Voodoo Doughnut, which sells doughnuts covered in Froot Loops or shaped like a phallus with cream-filled balls. (The shop also officiates weddings.) And don’t miss the regularly scheduled Adult Soapbox Derby or the food carts. Portland’s food carts have their own iPhone apps and trade journal, FoodCartsPortland.com. They are organized into food-cart “pods,” with names like Cartopia, Good Food Here and Cartlandia, a “bike-centric food cart superpod.”
Last month, Portland held its eighth annual Naked Bike Ride, a beery, movable party that doubles nominally as an environmental awareness event. The police sent out a press release reminding everyone that it is legal to be nude in public in Portland, but please wear a helmet.
The city’s effect on people goes beyond the urge to strip. Emi lived three houses down from us. She’d arrived in Portland, age 24, a gorgeous, perfectly manicured Gucci- and Prada-clad rich-girl princess. A friend of mine dated her for a while. Then she went full-on Portland. She shaved her head, gave away her iPhone, started wearing flowy dresses and spending weeks at a commune she called just “the farm.” She and the couple next door conspired to rip up all the concrete between their houses. Then it rained and her basement flooded.
Such dramas kept things entertaining, but after nearly two years, it became clear that none of my three very part-time jobs was going anywhere, and I started to feel trapped in Neverland. In September, I crash-landed on my mom’s couch in Manhattan, which meant I was spending most nights in Williamsburg and Bushwick.
But it wasn’t until I walked out of the Bedford stop during the cold light of day for the first time and saw 40 bikes parked on the sidewalk and a frozen yogurt truck and thrift-store racks in the street that it really hit me: I’m in Portland. But this Portland was in an alternate universe, where people have money and ambition!
“I get all the press releases from, let’s say, Third Ward,” said Robert Smith, an NPR reporter based in New York who went to college in Portland, referring to the crafty collective in Williamsburg that hosts art installations and offers classes in glass blowing and medicinal herbs. “They’re doing it on a sort of almost Manhattan kind of scale. When they do D.I.Y., they have the giant building and press releases and marketing opportunities and that’s great, but it seems a little too proud of itself.”