One of the options google maps shows for Utica, KY to Norfolk is basically U.S. 58. Though I haven't driven the whole thing, I've heard this is a great road for retired motorists to take across southern Virginia when they're tired of interstates. There are a couple of cautions, though.
58 west of Damascus is mostly 4-lane divided highway, with occasional shoulders. Traffic isn't too bad except "rush hours." This stretch is probably like most of 460. I'd suggest the Virginia Creeper rail-trail from Abingdon to Damascus, where the road hasn't grown as much as the traffic.
Martinsville would be a good place to find those back roads. Danville, as I recall, is fairly decent downtown (except for some rough streets), with a suburban sprawl girdle.
And of course, the whole Norfolk/Chesapeake/VIrginia Beach is an urban area.
Damascus to Independence is a nice mountain road. There's enough twists and turns to keep the traffic slow. It's pretty rural from there on, with the exceptions noted above.