There are a ton of good long rides winding up and down the bluffs in WI. You definitely need to watch the gravel though. Certain roads will have gravel all year long, but you can find some awesome roads that are clean. 60 near Wabasha and some tangents from there is fun. Some of my favorites in WI are Cty Rd H from Mondovi to 121, Cty Rd Q from 121 to Independence, Cty Rd D from Whitehall to 95. That's a pretty long ride from the Cities though, but a good day trip to ride around that area. Since 95 was brought up, I've heard a lot of good things about Hansen's Hold-Up as a food stop on the ridge that 95 runs along. Umyaya and I randomly rode past each other and met on Cty Rd 7 through Welch. That's a fun one too, but I've definitely gotten close to slamming into turkeys around the corners. I'm always up for a group ride...not much for organizing them, so just let me know when and where.