I got this 82 Maxim running for a family friend and he wants to take it to his son's house up in Bozeman Montana. We're seriously considering riding up there together, then I would ride back by myself. Wisconsin to Bozeman is quite a trip and very closely mimics the trip they take in Zen and the Art of Motorcycle maintenance. If you've never read this book, I can't say it's for everyone. But if you dig philosophy you're probably going to like it. We've both read it, and think it would be cool to replicate the journey.
Aside from that, I could spend a whole lifetime just riding around Wisconsin. And I fully plan to.
I've never been further west than South Dakota, so I think I can deal with some hipsters! They did say a lot of people have moved to the area in recent years. They really like it there but it sounds like there's even fewer riding months out there than Wisconsin