I'm from the city proper myself. I grew up in Carrick from about 4 until I left for college. I guess we lived out in Castle Shannon near my grandparents for a while, but I was too little to remember it. My cousins live out in the Murrysville/Monroeville area so I spent some time out there too.
I used to ride a lot as a teenager too. No matter how you sliced it I had to climb a big hill to get home! Too bad we didn't have anything like this forum when we were teenagers huh. I always used to think I must be just about the only cyclist in the city... 70 mile rides and I'd rarely see anyone else out on the roads (this would be back in the late 80's). All the kids at my high school thought I was pretty weird.... I don't think they could imagine much more than riding a loop around the lake at North Park on a bike...