Thank you for this!
Illinois
D: Cook, St. Clair (since 1972)
R: Edwards, Lee, Ogle (I in 1912, never D in the history of the Atlas which goes back to 1892)
Interesting, Edwards County last voted D in 1832, Lee County in 1852. Ogle County has never once voted for a Democrat for President. geoelections.free.fr/USA/elec_comtes/1852.htm
All 3 counties voted for Teddy Roosevelt in 1912 like you mentioned, but otherwise have all voted Republican since 1856. Even though they are 300 miles apart!
What's interesting about Edwards county is that it's in southern Illinois, for a long time a Democratic stronghold, so it is starkly contrasted with the Democratic counties surrounding it on many election maps.
I really don't know much about this, but I remember reading that - while Democrats certainly held most of the power in Southern Illinois - it depended on the geography. Contrary to popular belief, the southern third of Illinois is pretty different from Northern and Central Illinois, and it isn't just a bunch of cornfields. There were coal mines there, several areas of swampland and the Shawnee National Forest; it's actually quite beautiful. Anyway, I remember reading one time that the areas with good farming tended to be more Republican in the traditionally conservative Midwestern mold and the areas with less corn tended to be more Southernized and Democratic ... not sure how I could back that up, though, too lazy to look at the maps.