1. The limestone WI trails I've encountered are doable as long as you're on 28c or bigger. 25c or smaller would be passable but more of a struggle especially being loaded. There are some rotten granite trails in the state. Those would not be doable on anything less than a hybrid. But most of those tend to be in the northern counties. I hope you have your climbing legs ready, because the Dodgeville area is quite hilly, but beautiful.
2. I researched many of Wisconsin's counties several years ago to discover which, if any, counties permitted camping.
I pasted the original file into a google doc if you're interested. Some of the data did not transfer verbatim. The tabs are not labeled in the google version. And the last tab/sheet has/had a map of the state with the counties outlined and named. Stupid google. Oh well, it is free. If you like, I could email it to you. I originally did it in Excel but have since went to a Mac. I now have it in an Open Office file. A few of the links are broken, but most of the useful stuff remains.
https://docs.google.com/spreadsheet/...nc&usp=sharing
Good luck to you and your SO. Oh, and you will be in brewery country. So stop in at the Joseph Huber Brewery in Monroe, Ale Asylum in Madison, New Glarus Brewery (~15-20mi north of Monroe), et al....if you like great beer that is.