North US road trip

Calgary and Toronto are both in Canada (as you probably know, having driven between the two of them before). so unless you mean you're going to make the trip between the two within the US, you should probably ask on the Canada branch.

#1 - Yes, OP means making the trip between the two within the US hence the title.

OP - There's plenty, Mount Rushmore, Devil's Tower, The Wall Drug, Chicago. This website is great for finding stops.

Drive across the Upper Peninsula of Michigan for starters. Roosevelt National Park in NOrth Dakota.

What time of year is this roadtrip planned for? What are your interests?

I agree with eazeliff that Northern WI and the UP of Michigan is a good shortcut (rather than going around Lake Michigan and dealing with Chicago traffic), if time is an issue. It's more enjoyable to do Northern WI and the UP of Michigan in the summer than it would be in the cold. That route also takes you across the border at Port Huron/Sarnia, which is faster than muddling through Detroit/Windsor.

If time isn't an issue, then some of the places I'd stop at along the way include: Theodore Roosevelt NP in North Dakota; Minneapolis/St Paul; Madison WI; Milwaukee WI; Chicago.

If you decide to go to the UP and Northern WI, stop by the Boundary Waters in northern Minnesota. Very beautiful place, great boating opportunities.

I would suggest the following: From Calgary, head southwest to Waterton NP and enter the US at the border crossing between Waterton and Glacier NP. Explore Glacier and exit the park at Kalispell, Montana. Head south until you high Interstate 90 and from there, begin your eastward trip along I-90. There are a lot of most interesting things to see that I-90 goes near and if you yahoo or google road trips USA you'll see what there is along that route. Have a great time!

Drive south into Montana. Find U.S. Hwy. 12, an archetypal lonely western road, and take it all the way across those prairies with those waves of grain until you get to Minneapolis. Get on the Interstate and drive to Milwaukee. Take the Lake Express ferry to Michigan. Drive to Detroit, and from there you know the way. Along the way, check out some of the mansions listed in FAQ post 208: "Mansions and Grand Houses of America"

p.s.: Along U.S. 12, in Forsyth, MT, stay overnight at the Hotel Howdy. In 2005 it was $22 a night + a refundable $3 key deposit. Tell us if the price has gone up. Stroll along the street in the wind, eating dust, to the storefront church to see the list of names of local area residents serving in Iraq because there's nothing else for them to do. Let us know how many have died.

I'd choose US Highway 2. Take it from Montana, across the UP of Michigan, and then re-enter Canada there. US 2