After the relatively sparse plains the next leg takes us through some major cities and a wide variety of terrain. This leg also includes four of the five great lakes that we plan on trying to skinny dip in (though I’ve been informed that they will be fucking cold). With 45 days and 2200 miles this will mostly take place in the late summer and early fall… so hopefully there will be some beautiful colors along our path. Some highlights include:
- Antoinette the Cow
- Awesome Cities (Chicago, Green Bay, Indianapolis, Detroit)
- Six Flags Great America
- Cedar Point (a top rated roller coaster park)
- Lothlorien
- Our Haven
- Rock and Roll Hall of Fame
If you have recommendations for this approximate route I’d love to hear them… or if you want to host or know someone with a soft couch we are also always looking for new friends and family.
Wandering Oak 
I was born in Chicago, lived in Lansing MI for 5 years, and have spent a lot of summers in Northern Wisconsin…. so, basically, I’ve kinda been all around these parts here =) Here are my thoughts. And, granted, I don’t know about what you’ve already done and could be suggesting things you’ve already done and/or thought about. If so, apologies in advance!
– Heck yes come to Chicago! There are soooo many things to do here, it’s hard to suggest anything given I don’t know much about you. There are the traditional things, like Millennium Park, the Bean, the Lake, etc. Blah Blah. Maybe even a cool architecture tour? But you MUST — seriously, I demand it — eat deep dish pizza at Lou Malnati’s. There are a number of locations, so you will find one close to where you stay. You can’t leave without eating their pizza. Also, The Fudge Pot in Old Town has the most delicious chocolate. Also in Old Town is ‘Second City’ — an improv comedy club that’s pretty great.
– Galena IL is an adorable little town if you’ve never been there. Haven’t been there in a while, but they had good food, cute shops, and great coffee. Pretty hilly, too. Very scenic. Not sure if there would be a way to work that in…or if you’d want to.
– If there is a way to change your route in MI, I would recommend trying to do so. Specifically, going through the Upper Peninsula and then down Michigan would be beautiful. ESPECIALLY late summer/early fall. (A bit cold, though) That’s the only pretty part of Michigan — the Northern part. Although, I think it’s kinda similar to what you’ll see in Wisconsin, so perhaps that would get too boring. Have you been to Mackinac Island? It’s such a treat!
– I’d recommend adding in Traverse City, MI and/or Door County, WI to your trip if you can. Both are big cherry places, both GORGEOUS, and have cute shops/food/biking/etc. Door County is kinda close to Green Bay, so that’s already close to your planned route.
– A few of these are part of the “North Country Trail” — you may have already heard of it? That might be useful.
I hope these weren’t irritating to suggest, as you are clearly more experienced in touring than I am. Can’t wait to read more about this!
AWESOME!!! Thanks so much. Neither Anna or I have been to that part of the country so it is all new to us. This is the exact type of information we are hoping to discover from locals. Thanks so much… this leg of our journey now has a lot of edits to make. We are in no hurry so staying around the Great Lakes for an extra week or two is no big deal.
🙂 Thanks Echo.