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It's not crazy at all that you love the planning stage of a trip - it's not even uncommon. Planning a trip is a huge part of building excitement for a trip.
When you mentioned the upper midwest, US-2 was one of the first things that came to mind for me as well. I have not taken the Ferry route that Buck suggested, but I have made the drive from Toronto to SSM via Sudbury and found that to be quite enjoyable too. Lots of parks to explore in the Georgian Bay region of Ontario. While cutting down to South Dakota as Buck mentioned is a very good option, I wouldn't dismiss the idea of following US-2 all the way across Minnesota (going near the Mississippi River Headwaters), North Dakota (Teddy Roosevelt NP) and Montana (Big Sky Country and then Glacier NP).
If you do decide to use US-2, you might check out the bookRoadtrip USA, which has a nice guide of US-2, which it nicknames The Great Northern route. However, If you decide on US-2 or any other specific numbered route, I'd always encourage you to look beyond that specific highway, as there can often be a lot of great things just a short detour away. For example, instead of using US-2 across Upper Michigan, you might want to take some other roads that would take you closer to Lake Superior.
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Great idea...I will check that out. The idea of traveling as close to the southern shore of Lake Superior sounds appealing. Also have never done that while we have taken in many of the attractions in South Dakota previously.
Thanks for the help.
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Just off of US-2 in MN, near Park Rapids, is Itasca State Park. Its claim to fame is that the Headwaters of the Mississippi River is right on the shores of Lake Itasca. It's open in the winter, though you might not want to wade across the headwaters. :-) Seasonal update for the park is here.
Both Ashland and Superior, WI, have lovely views of Lake Superior -- or at least, they were lovely in the summer. I gather that Lake Superior can be very menacing in the winter. It is also COLD up there. My cousin in the area reported that it was -9 one morning recently. Brrrrr!
Donna
