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Missouri also does letters for county highways. But one thing unique to Wisconsin is that some highways aren’t just single or double letters, but an abbreviation of their destination, like the road to Whitefish Dunes state park in Door County is “WD”.
Siri calls them highways, they’re County Roads!

And I’m still searching for County Road PP. once I find it I’ll drive to it and the kids will laugh at Siri.

They’re CTH : County Trunk Highway. Posting from CTH T between the intersections at TT and TTT.
I grew up in Iowa and Wisconsin. Iowa’s road system is beautiful—a road every mile, every few miles a paved road, all either east-west or north-south. If you know the general direction of where you’re going, you can bumble around with confidence. It’s Manhattan over an entire state.

Wisconsin, nothing makes any sense. Sure, sure, Wisconsin is maybe a little hillier, but the roads curve and splice together in crazy ways in the flat valleys, too, and the roads adhere to no particular direction, and of course County B in one county bears no relation to County B in the adjacent county. And there are so many routes where I live in southwest Wisconsin where you might as well say, “you can’t get there from here,” given how indirect and circuitous the best route is in relation to how the crow flies. If you like driving for hours at 35mph while watching out for deer, Wisconsin’s county highway system is for you.

Someday Google Maps will learn not to pronounce County N as "County Road North"... That's not as hard as AGI right?
Because no other state has a combination of state and county roads.
I know for a fact both Texas and California have numbered county roads. The Central Expressway in Silicon Valley is Santa Clara County Route G6.
As a Sconnie native, the main thing that annoyed me about the letter system is that it's easy for the letters to rhyme; for example, near Verona (home of Epic!), there are (Dane) County roads PB and PD. Gotta enunciate carefully. :P This would qualify as a "usability issue" I would imagine. :)
> They needed to be able to keep them separate, and hence, they separated them by the numbers and letters

That's the how and when, but that doesn't actually explain why they had to use letters, does it? Even before computers and internet it seems like it would have been possible to devise a system across 72 counties to assign county roads a number that doesn't conflict with roads under other systems' jurisdiction.

one of my favorites is County Road AF, near Fall Creek and Augusta