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I live in Philly...which has turned into a very cycling friendly city. Even having a Bike Philly event this year, modeled after the Five Boroughs tour...
I haven't ridden in Pittsburgh, but I know a boatload of cyclists from that area. Most are racers, and very strong hill climbers, go figure
"The bicycle is just as good company as most husbands and, when it gets old and shabby, a woman can dispose of it and get a new one without shocking the entire community." -- Ann Strong, Minneapolis Tribune, 1895