The first time I saw the Chicago skyline...It was around January 20, 1984 and bitterly cold, with high temps in the single digits (
https://www.wunderground.com/history...DW/date/1984-1)
I had taken a bus from KC, alone, to visit the University of Chicago as a prospective student. I remember Lake Michigan being frozen along the shore and that long, long collection of skyscrapers. To that point, the only major league cities I'd ever seen were KC and the Twin Cities.
Another odd moment of amazement was the first time I learned about
Gopher and spent several hours hopping from one networked site to another on it. I remember reading about the Joe Montana trade and the first World Trade Center bombing on AOL, so maybe I first used Gopher a little before then, maybe 1992, but I'm not sure.