Back in my Navy days, when stationed in Norfolk, I did a lot of road racing. One of my favorite races was in Front Royal, VA ; during the fall. It was also timed to occur when color would be at or near peak. The 10k race went out and around rural roads; up and down rolling hills. Absolutely stunning.
However, that's pretty far from Wmsburg. Another good choice is the Skyline drive, starting at Waynesboro. Just zip up I-64 to and through Charlottesville. Blue Ridge Trail / Skyline Drive south of Waynesboro, I'm thinking, is probably going to provide the earliest color.
We camped in that area (Geo. Wash. Nat For.) when our kids were just wee liitle ones. Good memories.
Try this URL. If it doesn't display as Scenic Drives, then click on Scenic Drives and it should go there:
http://www.woodalls.com/outactiv/sta..._va.cfm#drives
Darn it. Now I want go back there. But me better half wants a month to recover from the Black Hills! Ha.
Denny_A