Greetings,
As a lurker in the weeds from the west coast, my suggestion for this kind of event, is look into buying a tent that can be set up. Kind of like the ones that you would see at an outdoor wedding.
Have some one or a group of some ones build a temporary stage that can be set up or stored as needed, strike that idea, figure out where you can put a flat car and build a removable set of back and side walls with a canvas awning on top. This would do several things at once, give you a railroad theme, a wood floored stage, and wind protection for the musicians. The getting of a tent would still be a good idea as when you have a function it can be set up so the public has some place to get out of the rain and if the tent has sides the wind also.
Out here in the Great Pacific North Wet we have several small music events that are well attended and looked forward to each year, defiantly this is a good idea. May look into partnering up with a local town's chamber of commerce or similar organization to help spread out the work of organizing something like this, because if this takes off other local bossiness such as restaurants, bed and breakfast's and so on will benefit also from it.
I don't know what kind of road access there is up the line but trying to move a lot of people back and forth on the railroad might try or over whelm the capacity of the railroad and if that happens and people can not get to the event or more importantly home from the event they will not come back, so try to find a place where they can park close to the event. In fact now that I think about this parking might be the biggest problem. Is there a church close by that you can use their parking lot and then use school buses to move people to the event is one idea that might be worth looking into.
Alright that is my two cents worth well maybe three cents worth, you can now get out the forks and knives and dice me up for my crazy ideas!
Andre
Portland Oregon