Thanks for the breakdown! Took me a bit of sleuthing, but route 151 crossing route 12 is unambiguous: you live in Madison, WI, and the picture was likely taken around one of the Verona-something roads.
route the highways around the edge of the city, instead of punching right through its heart
Wait, is the latter something that is still done? As in, newly planned highway right through the city? Or no, you're talking about the 50s.
the city does have some genuinely nice spots
It's between two lakes, that can't be too bad. I also live in a village between two lakes - nothing all that exceptional in Southern Finland.