C.O.
I believe there is a AMTRACK in Winchester, VA....Strasburg VA is about 30 miles south of Winchester....however, Strasburg, PA is about 3 hours north...you can go through Gettysburg....
It's been years since I've been to Strasburg, PA - there is a train museum if I remember correctly....other than that - I can't offer any tips!! SORRY!!!
Winchester can be fun - lots of revolutionary war history - about 1 hour from me!!