Good luck w/ your trip, I'm sure you're going to have a great time.
As far as your gearing/ equipment concerns, remember that nothing is set in stone. About 20 miles west of Charlottesville you're going to hit the climb up to the Blue Ridge Parkway. I was heading the other way but I presume that climb is going to be as tough as anything else your going to hit. The Parkway itself is pretty hilly but then you will drop down off the ridge line about 20 miles down the road.
Then you got about 200 miles of rolling hillside to decide if you want to change something with your bike. There's a beautiful little town called Damascus Va. right on your route before you hit the steep stuff again. Your map list's several bike shops in town but all except one are bike rental places that are of no use to you. There is one real bike shop, it's called Adventure Damascus. It's easy to spot, the facade looks like it's a replica of a 60's rock album cover.
If that first big climb shook you up, here's your chance to change your gearing. After Damascus starts about 250 miles of the hilliest part of the trip unit it flattens out around Berea, Ky. Also, there are post offices all along the way. If your not using something, get rid of it. You will notice every couple of lbs you can shuck off.