I did a ~2000mile, 7-day road trip in February with a friend, starting a couple hours north of Toronto, going through 10 states (admittedly 3 of them were pretty well only entered for the ability to say we'd been there) and back where we started. The route was roughly this:
Barrie, ON, Canada to Barrie, ON, Canada - Google Maps (google maps)
It was incredibly awesome, but I would have loved to have had twice the time to do the trip in, so we could have actually seen more of the places. Hopefully in a few years once I've finished my degree and earned some money I'll be able to head back and do a similar thing again, with a bit more time.