I rode Skyline Drive in early Nov. and it was fine. Two years ago I did the C&O canal in Nov. and it was also fine (mid 60's). I don't think the weather will be a problem for you. I would take the train to Charlottesville VA and you can ride south on the Blue Ridge Parkway and north on Skyline Drive.
Charlottesville is a very cool town and would be a great hub for riding that region.