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Alright, I have a ton of suggestions and am waiting for a flight to finish boarding. The Driftless area in general is chock full of sweeping turns, elevation changes, switchbacks, and beautiful scenery. A particularly great stretch of highway is 33 west of Reedsburg to La Crosse. A 2 seater club I have driven with refers to as the Tail of The Badger. The stretch past Wildcat Mountain state park is awesome.
Closer to Illinois, departing west on Janesville 14 then heading north on H to 59. Take 59 west to 1 north then head West on 92 to W. W west has a fantastic wide sweep with a great Hill climb up and then down into New Glarus, which is a cute Swiss Village with some great restaurants and the eponymous brewery. Heading west out of New Glarus provides some great roads, highway h south of town is particularly great. From there, there are tons of great options.
If I get time I will follow up with some actual routes and Google maps links in different areas but wanted to keep this thread going.
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