>>2662343Ice Age Trail is unironically about a quarter of OP's route. Wouldn't work on bike though.
>>2662340I wouldn't do that during winter time. If you actually want to enjoy a Wisconsin+UP ride, I'd recommend going when it's not insanely fucking cold. Milwaukee is fine as long as you stick to the bike trails on your way through. That's like the best possible halfway point. Anyway shit I'd recommend on a bike packing trip of this flavor
>Fields Museum in Chicago>Bobblehead Museum in Milwaukee>Manitowoc for the Sputnik crash site (it's not all that cool but it's not too far out of your way)Keep in mind north of state highway 8 is skinwalker territory. The UP has plenty of mines, both abandoned and active, so explore at your own risk. Are you planning on biking back south afterwards or do you have travel plans for your return trip?