Living just south of Pittsburgh I will say once you get out of town it should not be too bad. There is wood lands of decent size once you get to the county line. It is getting out of the city that's hard. From the city center there are five level routes and two useable routes over Mount Washington. I would aim for the old Walbash tunnel or the trolly tunnel at the end of the Smithfield Street bridge. There are two major routes south one is the US 19, the other would be I-79, personaly if I was travaling on foot I would follow US 19 about 13 miles, that will get you to an aera with several good lay over points, you may want to look at the area around Mayview State Hospital, If you stay on on or around US 19 until just north of Washington PA you should be able to go around Washington and pick up I-79 south into West VA. Most of the useable routes around here have roads running along them. You may find some of the old Mass transet lines and rail lines from the coal mining days a good path for bicycle or walking. I think there is one running along the Ohio River but do not think it would be the safest route. Do not try to go through the West End. We have an office there and have to watch ourselves at night around there. The North Side (Across the Allgheny River from town) is another place I would not go near in a bad situation.