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Originally Posted by driveway
As someone said above, Deadwood is 100% worth a stop on that trip, and I think you should make a stop in the town of Wall, South Dakota to visit Wall Drug.
http://www.walldrug.com/
Also, if you're heading down from Calgary, hitting the Little Bighorn Battlefield is pretty much right on the way.
South Dakota is a massively underrated State. It's seriously cool, the Black Hills are absolutely incredible, like Drumheller but somehow even a more extreme landscape.
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You can also get a tour of a minuteman missile silo and see badlands that dwarf drumheller. Custer state park has some amazing lakes and needles rock formation and you can hike to the highest point in South Dakota. And get tours of wind and jewel caves. There is at least a weeks worth of stuff to do on a trip.