I don't know the answers right now, but it should be fairly easy to get them. The Settle-to-Carlisle train is still running. I rode part of that route in the summer of 1997. You need to find the proper Ordnance Survey maps of the area, (they are downloadable at http://www.ordsvy.gov.uk/) and look at the names of towns, villages, hills, valleys, and other features along the route. I'd bet you'd get most of your answers in short order.