I've driven from Cincinnati to Colonial Williamsburg at least 15 times, either directly from Cincinnati or south from New England or north from Florida. But there's no rules that I've found for filling in the "visited states" map or any way that I've found to just update the map instead of starting over.
Do you fill in a state if you drive thru it or must you overnight in it? Must you be RVing at the time? I've driven in several states and a few Canadian Provinces while working, but I flew in and rented a car, so I don't count them. I drove into Tijuana, MX in a car for a total of about 2 hours without ever getting out of the car, so I didn't count that. The only states I've never been in by any means are Washington and Oregon.