What Is An Alleycat?

The defining elements of an alleycat are pretty basic, leaving the design of the race largely up to the organizer’s imagination. A lot of the times it’s a matter of how to make it as fun and challenging as possible.

“The alleycat is its own special thing, the perfect combination of these skills that you just kind of develop riding around and getting to know your city,” says Jeff Frane of All-City Cycles and Bike Jerks Minneapolis.

The basic structure includes a manifest, checkpoints, and challenges; like a scavenger hunt, you have a set of locations to get to, but you can get there any way you want. On top of being laid out on the most challenging streets, add into the mix a host of checkpoint challenges. Just about anything that you could think of making someone do is fair game for an alleycat challenge.

When we started it was very basic,” says Squid. “The first Halloween one that we did, everyone put in $5 and it was winner take all. After a while different cities started doing stuff that was a little more fun or different. The Boston kids were probably wackier than most. One time there was a checkpoint a block away from a police station and they had boxes of donuts, and you had to take a donut and throw as close to the police station as you dared.”

One popular sentiment in alleycat culture is that it’s fun to suffer. What that translates to in the alleycat community is races scheduled for the most grueling time of year, in the dead of winter. The long-standing St. Valentine’s Massacre Race was among the first to set this precedent.

“Race to a checkpoint, drink a beer, do something silly, fix a flat, answer a question, play hopscotch—whatever you need to do to get your manifest signed to head off to the next checkpoint or a race meant to simulate a day in the life of a working messenger, for example, picking up packages or envelopes and routing yourself to the next pickup/drop location,” says Sean Martin, describing some of the possible challenges that face alleycat racers. Martin, who hosts the grueling Lord of Griffith fixed gear hill race every year, began throwing races to pass on the fun he’d experienced at messenger-hosted events.

Growth and Sponsorship

Sponsors have been involved since the early days, but as the scene grew organically by word of mouth, more companies found reasons to get involved. The first major sponsor on record is Dunhill Cigarettes who lent their support to the Toronto alleycat scene.

“In 2003 we did a dispatch-style race with Bodyglove... for some reason they thought New York messengers were tough or something like that, so they wanted to do an event that had a lot of messengers showcasing their gear,” Squid reports. “We helped them get a ton of messengers together and rock their jerseys and do a ‘work challenge.’ Basically an alleycat, but we made it look legit. The way I look at it is it’s good exposure for cycling and if big companies are gonna help us out, it’s up to us make the best out of it, ya know?”

In 2004 Puma approached Squid and several other NYC messengers about putting together a track team. The following year, the company sponsored CMWC in New York. Over time, others in the bike scene started throwing alleycat-style checkpoint races. Although messengers have a familial community, it’s certainly not made up of exclusively messengers—family, friends and the like have always been involved to help run checkpoints and generally be a part of the fun.

“Fast Friday was started by Dustin [Klein] but was assisted by non-messengers,” says Martin “It was the community getting behind each other and progressing the fixed gear scene. It wasn’t about messenger or non-mess, it was about the bike, the fixed gear and what could be done with it.”

The emergence of localized bike forums online opened up a new channel for people to find out about and organize events everywhere.

“People on the Bike Forums Single Speed and Fixed Gear board put together a full-scale alleycat in Chicago in 2005,” David Munson, long time Chicago area rider and photographer, recalls. “It was primarily a non-messenger crowd. People came from all over the country. It was the ‘BFSSFG Meat and Greet’ with meat spelled like animal flesh because we were all meeting up in meatspace. It was the first time I think I really saw that a not-necessarily-messenger urban cycling event could actually work.”

With the support of these forums races grew in attendance and frequency, and the first decade of the 21st century saw the streets blush with fixed gear fever. It wasn’t always that way, though.

“A lot of guys are trying to do all these alleycats on brakeless track bikes,” say Hilliard. “When [alleycats] started out messengers would just ride whatever two-wheeled thing they could throw together.”

“Nowadays, everyone worldwide are throwing street races,”says Martin “It was a natural progression from what messengers were doing worldwide back in the day. Riders wanted to show their bikes, tricks, bike handling and of course who was the fastest. There was always non-messengers racing alleycats throughout the years, but the explosion of the fixed gear bike through blogs, forums, word of mouth, shops, etc. really made it accessible those who didn’t know messenger culture.”

The downside is races getting blown out when they get too big to fly under the radar, cyclists coming out just get prizes, others overestimating their handling skills or underestimating the force of a car that has the right-of-way.

“An alleycat is typically an illicit thing, and is best manifested in a subculture that’s not going to spend a lot of time blabbing about it online before the fact,” says Munson. “The more popularity grows in more mainstream parts of the culture, the more at risk the tradition is put. There is real fallout from it. Word got around a bit too much in Kyoto in 2009, for example, and the main race of Kyoto Loco had to be cancelled because authorities had caught wind and leaned on the organizers to stop it.“