I was reading another article about Susan Kare, the designer of the fonts and icons for the early Mac, and I came across a strange comment that the original fonts—Chicago, Monaco, Geneva, New York, etc.—were originally named after towns near where I grew up in suburban Philadelphia. I googled, and I got this Folklore entry, written by Kare herself. Apparently they were named for stops on the Paoli-Thorndale bound R5—Rosemont, Ardmore, Overbrook, Merion. Also, see this interview.