I live a little over a mile away from my parents, and there's a nasty 20% stretch when I ride over there. Fortunately it's pretty short but when I was in high school, I didn't have the strength and/or gearing to make it up without stopping to walk it. Some years after college when I moved back to the area and started riding again, I got a bike with a triple and was pretty pleased the first time I was able to make it up without stopping.
A couple of years ago I rented a bike while visiting Pittsburgh, and hit some of the Dirty Dozen hills, including Canton Ave (cobbled!). Definitely some seriously steep and nasty stuff around there; good times though.
Have you ridden up Canton Avenue? It's been called the steepest street in the country, although there is one in San Francisco and one in Hawaii that might have it beat. Top 3 for sure. I would love to try that. But not in clipless pedals. Would need to be ready to abort.
