So many possibilities, and almost all of them great.
Here are a few hilly challenge rides in the driftless areas you will be traveling through... if you don't mind hills, stitch a few of these together and you'll have a wonderful time. Stay off 14 and the major roads.
https://www.horriblyhilly.com/wp-con...H-Map-2019.pdf (don't miss Mounds Park Rd and turning to climb to the top of Blue Mounds Park)
https://ridewithgps.com/routes/5419886 (the Kickapoo Kicker route... Wildcat Mountain is a must)
https://ridewithgps.com/trips/353353 (Dairyland Dare)