Trip/Route Advice

[Chili]

My wife and I plan to hit the road about 2.5 weeks ahead of the day we need to be in Canmore Alberta for the Northwest/Western Canadian Rally and are trying to decide where we want to explore. Coming out of Winnipeg, Manitoba, we are considering either working our way down to Minneapolis/St. Paul and heading south along 61. We've been down this route plenty at least as far as Lake City before heading back west a bit to Spring Creek MX for the motocross races. The other option is heading down through Duluth underneath Superior before turning south on #2 and down to Milwaukee and then working back west.

Looking at the NCR brochure looks like some nice areas to explore, any must see's or tips for the area? I've heard Galena is interesting but other than that my entire exposure to WI, IL and surrounding area is on the slab in a cage.

From this area we are then looking at routes west to make our way through Grand Tetons and Yellowstone as they got removed from last years trip due to days lost due to a clutch failure.

Appreciate any advice and must see's anyone wishes to forward.