I STOOD for a long while, pretending to contemplate my bike chain while I stared at the hill. I would never get up it. I was in the middle of rural Oregon, still 35 miles from Portland, getting passed one-by-one by 34 custom bike builders. I was going to die out here. If not from exhaustion, then from the embarrassment of having to hitch a ride in the sag wagon. Either way, death was near.

The builders and I had all started out two hours earlier from a humble field in Buxton. The 50-mile ride was a grueling test for bikes entering Oregon Manifest—a national bike design competition that culminated in Portland last weekend with a block party, a $3,000 first prize, and, I feared, headlines of "Unathletic Reporter Vomits on One-of-a-Kind Bicycles."

The competition challenged builders from one-person shops and major schools (including University of Oregon) to craft the "perfect utility bike." The results were innovative city rides sporting gorgeous racks, pedal-powered lights, cupholders, a USB cell-phone charger, and even a sidecar for a dog.

Portland has at least 157 bike-centric businesses, but many of them are small one- or two-person operations. For better or worse, a substantial chunk of Portland's $63 million bike economy revolves around high-end and artisan cycles. More than 30 bike builders have set up shop in the city (Oregon is home to the nation's only bike-frame building school), each slowly turning out handbuilt bikes like the ones that Manifest showcases. This fits well with the city's small-batch aesthetic, but mass production (and mass employment) it's not.

Joseph Ahearne, who crafted a bike outfitted with not one but two whiskey flasks for Oregon Manifest, gets by teaching and building only 15 to 20 bikes a year.

"The business model is very difficult—it's really hard to compete with Asian-made bikes. It's a niche of a niche market," says Ahearne, who also bemoans that a major bike company, Soma, recently released a mass-market bike that closely mimics a design for a cycle truck he pioneered a year ago. He's hoping to stick around Portland for the community, but, honestly, is considering moving to Vermont for free health care.

Meanwhile, a woman on a bright orange Portland-made e-bike (as in, electric) rolls up next to me at the bottom of the hill.

"You're killing it!" says the rider, Diana Rempe, while her four-year-old, Violet, waves happily from the bike's child seat. Rempe switches on the bike's battery-powered assist and with a few strokes of the pedal and a whrrrrrr of the electric engine, heads off up the hill. Though I'm too far behind to see it, at lunch everyone is talking about Portland builders Tony Pereira and Ira Ryan, who were amiably riding side-by-side up the steepest stretches. That is, until Pereira hit his magenta bike's electric assist, popped a wheelie, turned up the Led Zeppelin blasting from his built-in stereo, and left Ryan in the dust.

I huffed and puffed my way up the hill, swearing every third breath and eventually stopping for blackberries and commiseration with some people piloting the competition's heavier cargo bikes. Farther along, near the top of the 1,000—foot climb, I crossed paths again with Rempe. The wires on the e-bike had jostled loose, so she was now biking the 100-plus-pound bike and child uphill with pure muscle. This, indeed, was the pain of innovation.

Finally, I managed not to vomit on anyone and we reached the downhill. The ride ended at the largest bike business in Portland: The Northwest industrial headquarters of bike parts manufacturer Chris King Precision Components. Chris King is as big as bike industry gets in Portland, employing 92 people and exporting high-end, American-made hubs and headsets to 27 countries. I collapsed in their gourmet cafeteria. At the end of the night, Pereira is awarded the best-in-show prize. For some reason, the wheelie is not specifically mentioned.

More photos of the Oregon Manifest bikes and ride here!