The main state university in Massachusetts is like this. There was no centralized planning that wasn't hobbled by historical preservation efforts. So it's just a bunch of old buildings wherever, and then they did just that. Just paved whatever paths warn down in the lawn.

The campus is chaos, and it's basically impossible to navigate because of the building issue. They have started to correct this in the last decade. But to me, it's losing its charm. Nothing better than going into a building built 100 years ago, only to realize after missing the first class that you have to walk down this weird side hallway, over a catwalk to an entirely different building, but uses the old buildings naming convention. Just pure chaos, it was awesome. Oh and fucking with freshman is too easy, it ia hard enough to legitimately help them.