Thanks for the responses. As usual, differing, yet still good advice. Might HAVE to go counter clockwise. I live in West Virginia. If things go as I hope, I'll start in March or April, ride over to the Chesapeake, VA area and roll north. THANKS
Minor thing, but if it were me, I'd be aiming for Washington, D.C. instead of Chesapeake. If you're going to hit the TransAm, you'll be nearer D.C. than Chesapeake by the time you get to Charlottesville, so Chesapeake to D.C. will be back-tracking. Also, you could take Skyline Drive northeast to Front Royal, and be within a day's ride of the C&O Canal, then within a day's ride to D.C.
(Unless it just rained hard, then it might be best to skip the C&O and hit the Atlantic Coast in Pennsylvania.)