I Can’t Canton

August 18, 2020
22.65 miles
South Side

Pittsburgh is overall a notoriously hilly city, but perhaps the most notorious hill of all is Canton Avenue, which is on record as the steepest street in the continental United States at an absolutely insane 37% grade. When I heard about this, I knew that I had to try it at some point, and on August 18, 2020, I made my first attempt.

The annoying thing about Canton Avenue is that it’s pretty out-of-the-way; I actually had to ride for about an hour and do more than 1,000 feet of elevation gain just to get to the hill. There are two major bike routes to get there from Oakland:

I took the latter option on the way there and the former on the way back, although I wasn’t very comfortable riding a short connector on Saw Mill Run (which is technically a highway), so I ended up meandering through some local roads. The ride there was a little taxing due to all the climbing, but the beautiful descent on the way back sort of made up for it.

As for Canton Avenue itself: to spoil the ending, I was not able to bike up continually (as per the rules of the Dirty Dozen), although I was able to manage it by stopping a couple of times in the middle.

The vaunted Canton Avenue in Pittsburgh. Like all hills, the pictures make it look less steep than it really is. (full resolution: left, right)

The first strategy that I tried was just charging straight up the hill. This was actually fairly effective when I was still “fresh”, and at one point I very nearly made it to the top. However, as my legs got increasingly tired (recall that I had to do >1,000 feet of climbing just to get here in the first place), I quickly wore out and couldn’t make it that far by going straight up the hill.

The next thing that I tried was making “S” figures up the hill to decrease its apparent steepness. This was somewhat successful, but the tricky part is that Canton Avenue is largely cobblestone (well, Wikipedia informs me that they’re technically setts), so it is actually quite hard to turn around at the corner of your “S” (since your wheels tend to slip). It did not help that there were loose dirt and leaves on the road. At least it wasn’t wet!

When it was clear that this alone would not work, I decided to shed as much weight as I could; I left my water bottles and bags at the bottom of the hill before attempting again. This seemed to help a bit, although by this point I was already pretty tired. Quite unfortunately, a car also drove up the hill during one of my most promising attempts, forcing me to move to the side of the road and abandon the attempt. (Yeah, blame the car…)

Actually, the scariest part of incredibly steep hills is definitely going down. I did not dare to attempt to ride down the hill (I later found out that there was a “do not enter” sign at the top of the hill anyway), but it was impossible to even push my bike down the hill without losing control of it. The only safe thing to do was to lift my bike entirely and walk down with it.

Eventually, I tired myself out to the point that I was making less and less progress up the hill on each attempt. I tried motivating myself by eating a Clif Bar, but it did not help. After at least seventeen attempts to get up the hill (I started losing track toward the end), I decided to call it a day and head back home. I look forward to returning one day to conquer Canton Avenue.

I do wonder what would have happened if I had tried the “S” strategy and shed all of my extra weight earlier on, when I was less tired. Or what if that car had never passed? Would that have been enough to get me to the top? Overall, failing to get up Canton Avenue was a great, humbling experience, and it gives me a goal to work toward.