I had the same feeling the first time I flew to the west coast after my first cross country trip, in 1998. A large part of the flight followed near one of the routes I'd driven (I did sort of a circuit, to SF on the way out, and from Portland OR on the way back, so I drove two different routes).

These days, though, I pretty much expect every flight I take in the US to pass over places I've driven :) It's still really cool, but in a different way.