Bent Alley Cat Bicycle Races

Nope, that’s not a typo; the Bent Alley Cat Races has yowled to life.

That the name of this new DIY bicycle race series is spelled “Bent,” and not “Bend,” speaks to the off-kilter, fringe-y place that bicycle messengers — and all their trappings, like fixed-gear bikes and alley cat races — occupy within the greater cycling culture.

The Bent Alley Cat Races — very likely the first alley cat organized in Bend — began Aug. 7. In short, an alley cat is like a scavenger hunt whose checkpoints you connect in the shortest route possible.

Your intrepid Source reporter — a former bike messenger himself — took part in the race, which meets at Mirror Pond Plaza (in front of The Commons Café & Taproom) at 7:30 pm, each Thursday through October. Racers roll at 7:45 pm. A helmet and, crucially, bike lights, are mandatory. There is no race entry fee because Sean Taylor, the organizer, wants the event to feel like a “loosely organized competitive group ride” instead of a race-race. (And no, you don’t need to have been a courier to take part.)

Last Thursday, five racers showed up, quickly identifiable by their bikes. Luke Serrano, 19, and Charlie Sherman, 20, both students at Oregon State University-Cascades, arrived together on a fixed-gear bike and a single-speeder, respectively. Serrano’s bike was already experiencing a mechanical.

“I hope the fork doesn’t fold in on itself,” Sherman told Serrano, to whom he’d lent the bike for the occasion.

Serrano, in nosing the bike over a curb on the way to the race, misjudged it; he cased the fork so much the front wheel jammed against the frame’s down tube.

As they continued trying to rework the fork, José Liscano arrived on a geared road bike. Samy Metcalf appeared on a single-speed bike. Out of breath, she explained that she’d almost been t-boned by a driver. I joined the crew, as did Adam Shapiro, another former bike messenger and frequent alley cat racer. He told me he worked in San Francisco between 2009 and 2015 — the same years I worked in Manhattan. Shapiro soon ventured out to man a checkpoint in Riverbend Park; he wasn’t racing because he’d bruised his ribs on a recent mountain bike ride, shortly after completing the Oregon Timber Trail with a friend.

Race promoter Sean Taylor, who’s 39 and has worked as a messenger in San Francisco, Sacramento and New York City between 2004 and 2011, spread word of the fledgling underground race series by handing out flyers downtown. He profiled less the cyclists than their bikes. Someone got an invitation if their bike looked fast yet had tell-tale signs, such as well-worn handlebar tape, of being ridden hard and often.

Taylor, who now works as a cabinet maker and food cart slinger, said he decided to throw the alley cat series because he wanted to expand his social network beyond his tight group of friends. He also wants to cater to a niche in Bend cycling he says is underserved — urban group riding.

“I’ve gotten a lot of positive support…I’ve been really surprised,” he said. “It’s nice to know that there are bike shops and mechanics in town who want to see more of a shift in bike culture here to make it more inviting for urban riding.”

For the uninitiated, an alley cat race simulates the rhythm and chaos of a typical shift of messenger work: ten minutes before the race’s start, the organizer distributes handbills printed with the manifest, or a list of checkpoints. They’re not in any order; racers use their mental map to connect the dots in the quickest way possible before returning to the start/finish. Volunteers stationed at each checkpoint initial racers’ manifests to prove arrival. An alley cat winner isn’t necessarily the fastest; knowledge of the streets — and awareness of traffic-snarling events, is key. Short on volunteers, Taylor directed racers to take selfies of themselves at each checkpoint — that week, mostly roundabouts.

Per alley cat tradition, Taylor directed racers to position their bikes at a distance. After a countdown, he yelled “Go!” and we sprinted to our bikes.

Serrano and Sherman lead the pack through the Welcome Arch, but while walking; they were mindful of pedestrians. Off and pedaling, we checked off an easy downtown checkpoint before pace-lining through River West and soon toward Northwest Crossing, where several checkpoints waited for us on Mt. Washington Drive. At one, Serrano dismounted and began hammering his drivetrain with a rock — a crank arm had come undone several times on the ride there. The improvised repair worked; soon we snapped panting selfies at more checkpoints as we rode down toward the southern-most stop — the kayak sculpture in Riverbend Park.

I realized I’d forgotten a Mount Washington checkpoint and doubled back. Opting to self-navigate from the get-go, Samy Metcalf zipped past me toward the kayaks. Once there myself, Adam Shapiro, the race volunteer and former messenger, signed my manifest and directed me, as he did the others, to dip my front wheel in the Deschutes River. Serrano, Sherman and Liscano had already completed the task and took off toward the finish at Mirror Pond Plaza. Nearby teenagers mocked me while I scampered across the beach, holding my bike like a suitcase.

“He’s stealing a bike! He’s stealing a bike!”

Complicating our direct route to the finish was traffic control related to a show at Hayden Homes Amphitheater by Tedeschi Trucks Band. Certain I’d find the shortest route and secure the win, I rode wide, time-trialing it to the finish.

I was third. Luke Serrano had won, with Charlie Sherman in second, José Liscano in fourth, and Samy Metcalf carrying the red lantern. Completely anaerobic, we cracked the beers Taylor handed to us. In trading race notes, we tabulated an embarrassing list of errors. In his last few miles, Liscano, smelling burning grease, realized his front axle had nearly slid out. He ran the last half mile, he said with a laugh. Sherman detailed the caveman handiwork that had kept his crank arm — kinda — in place.

“I pedaled the last half of the race with just one leg!” he said.

For my part, my seat post made death creaks the whole race — I’d neglected to tighten a crucial bolt.

Taylor was unfazed.

“Everything that happened worked out well,” he said, adding that he hadn’t anticipated the amphitheater crowds. “But that is very much in line with what you would experience as a bike messenger. I can’t believe everyone pulled it off. I’m so stoked.”

Most racers finished the race in about 11 miles with 350 feet of climbing. Newly bonded, we chatted well into dark.

Metcalf, 28, is a daily bike commuter who had never entered a race. She said she was keen to try out the Bent Alley Cat because she’d found a race flyer, which features a cyclist with a screeching feline perched on their helmet.

“The flyer made it look fun, super inviting,” she said, adding that she’ll be there for the Aug. 14 race. “I’m not a competitive person, but the race was very fun and casual — you just do the best you can do.”

For each week’s Bent Alley Cat Race, Taylor will come up with new checkpoints. As for the Aug. 14 race, he offered a checkpoint hint: “wet tires.”

“I love that Adam [the checkpoint volunteer] came up with the river-dip requirement on the fly,” Taylor said. “This week, we’re gonna have a lot of river dips!”

This article appears in the Source Aug 14, 2025.