Well, taking backroads CAN be rewarding, even if it's in Indiana. I drove to the East Coast from Illinois a few weeks ago, and I took the backroads through most of Indiana. When I came to downtown ANGOLA (small city in N/E Indiana), I was shocked (positively) to see its great downtown city square. It was not car-free, but it had a nice monument in the middle of a small park, roundabout, plenty of benches to sit on, and awesome local businesses in the square.
What I'm getting at is this: the idea of a square in the middle of a city is nothing new: most European and South American cities, for example, have one, usually in the middle of their historic downtowns. However, in North America the "Business Districts" lack pedestrian scale, contain more parking lots than anything else, and are basically unattractive and uninviting.
So, what's your favorite downtown square in North America? (Hard question, I know, there aren't many around..)
Downtown ANGOLA, INDIANA: