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NW Wisconsin | I would make a few additional suggestions to see in the UP & Michigan area.
In the UP, Houghton is a scenic college town with Michigan Tech. See the Painted Rocks National Park via boat cruise. There are a lot of waterfalls in that area. See the locks at Sault Ste. Marie.
Staying on the island for a night is worth considering. It probably will be a once in the lifetime experience. Drive South from Mackinac to Petoskey. A beautiful town next to Charlevoix. In Charlevoix there are 20+ house designed like nushrooms and neat to see. Just West of Traverse City is Sleeping Bear Dunes National Park. It has an enormous 400’ sand dune that overlooks Lake Michigan. There several wineries, farm stands, and interesting sites in that area.
Then travel South to Ludington and take the ferry to Manitowoc. That gets you out of Chicago, and can take 151 back to Dubuque. You will see lots of dairy farms and agriculture along that route.
Here are some links:
https://www.petoskey.us/
https://www.visitcharlevoix.com/
https://www.nps.gov/slbe/index.htm
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Mackinac Bridge/island Vacation?
