Riding Pittsburgh’s Dirty Dozen

The author tackles Canton Avenue’s 37 percent grade.

By Karen Brooks, photos by Jon Pratt

Somehow I have lived and cycled in this city for 20 years without participating in one of its more famous bike events: the Dirty Dozen. This is an underground race of sorts, put on by Danny Chew, local hyper bike guy celebrity and two-time Race Across America winner who likes to dish out punishment—er, invite others to join in his idea of fun, which involves ridiculous amounts of miles or silly feats of leg strength. In this case, the idea is to climb a baker’s dozen of Pittsburgh’s steepest hills in an enduro-style format, doling out points for those who make it to the tops fastest.

Before those of you from Colorado or San Francisco snort in derision, know that Pittsburgh boasts possibly the steepest paved street in the world, Canton Avenue, a cobblestone monster with a 37 percent grade. (Some town in New Zealand claims they have one steeper than that, but since it would involve an expensive plane ticket to go find out, we’ll just go ahead and call Canton the steepest.) None of the hills in the Dozen are below 20 percent grade. Sycamore Avenue, a brutal climb made famous by the Thrift Drug Classic race that used to be held in Pittsburgh (once won by a certain Mr. Armstrong) is arguably the easiest of the hills.


Two-time Race Across America winner Danny Chew, above left, has been hosting the event since 1983.

So this year I finally decided that any excuses I might have thought up would bow down to the need to experience this ride. I’d been told that despite the brutality, it was lots of fun, a great rolling tour of the city with an atmosphere of camaraderie. Non-serious bikes and outfits were welcome. I hadn’t done any specific training at all… well, aside from the fact that coming home late from the bar on Thanksgiving Day, about 30 hours before the race, I decided to ride up one extraneous steep hill. So what—as Adam, the Bicycle Times web editor, and I told ourselves at the start, we were there simply to cover it for you dear readers, not necessarily to be competitive.

The turnout this year was much bigger than in previous editions—more than 300 in all—perhaps due to entertaining exposure of the 2010 edition by local public television documentarian Rick Sebak and his broadcast on WQED. The mild weather didn’t hurt, either. Adam and I found ourselves at the back of a very big group to start, and the first hill got underway before I realized it, with no fanfare or even markers to speak of. I passed a bunch of people, but the scorekeeper at the top had long since moved on by the time I got there. It seemed that some road racing skills would be needed to grab a better placed before the next hill—too bad I don’t do road racing.


Above left: The ride rolls across one of Pittsburgh’s countless iconic bridges. Above right: A local cyclist knew as “Stick” was one of five supermen who completed the ride on single speeds.

These hills really are brutal, though, and I didn’t want to burn out before the end. I had installed a mountain bike cassette with a 34-tooth big cog on my ‘cross commuter, for a 38×34 low gear—low enough, I hoped. I had also put on 32mm tires for some extra squish for the cobblestones, and a new chain for luck. I used that low sucker for every hill, despite the fact that I hadn’t tightened the B-tension screw enough and the derailleur pulley rubbed the big cog. I also had to remember not to shift into “big-big”—and forgot once, only to have a seasoned racer-type dude yell at me: “What are you DOING to your DERAILLEUR!”.

The equipment choices paid off. I gradually worked my way toward the front of the pack and began to catch sight of the fast racer-type chicks that were obviously winning. I even passed one of them on a long hill. People with high-end road racing bikes sporting big gears were speeding to the front, only to struggle once the real pitches kicked in, barely turning over the pedals, while I could spin (sort of) along and even sit for some bits. (Don’t get me wrong, though—the fast people at the front were mashing their way upward with big gears like the super-human machines they are.) A kind fellow racer began giving me a briefing before each stage. I finally caught sight of the scorekeeper at about the fifth hill, and apparently nabbed some points.

Very few riders made it up Canton Avenue on the first try.

Then the monster loomed large: Canton was the ninth hill. I made my assault on the wall of cobbles only to be turned back by another racer falling over in front of me, a common occurrence. I shouldered my bike back down the stairs that pass for a sidewalk here to make another attempt. This time I made it up in one effort, channeling mountain bike single speeding skills and buoyed by the shouts from the crowd pressing in around the course, le Tour-style. At the top, the scorekeeper not only remembered my name, she told me I got second place!

From then on, it was on, so to speak. I even won one of the stages, the next-to-last and seemingly the most offensive, a series of turns revealing pitch after pitch, each more hellishly upright than the last. I almost cried at the top. But then I caught my breath and tried to wipe my memory clean to maintain a positive attitude for the last push.


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