I'm from Pittsburgh (originally) -- the city quiets down a lot at night. I wouldn't expect to see very many people out at all at night unless you're near where all the bars are.

And yes, Pittsburgh has cabs but I think you have to call and order one, not like NY where you can just flag one down. Some of the busses even have bike racks -- but I bet at night, they'd let you wheel that thing right on and hang onto it while you rode. You could call PATransit to confirm. They run all the busses there.

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When you get up through Williamsport, MD area, if you need anything, send me a PM -- I'm about 10 minutes from the Williamsport C&O entrance.