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Wind Cave National Park is a gem. For riding pleasure the "Wildlife Loop", Needles Highway, and Custer State Park are wonderful.
What others said plus do not miss the Crazy Horse monument which is even more impressive than Mt. Rushmore and still not finished.
.Wildlife loop is a must do.watch for goats on the road.
if you plan on slabbing it via I-90 then the best advise i can give you is to avoid Chicago at all costs. a couple of years ago i went from West. Co. NY to the national in Gillette WY and found getting through Chicago was the worst part of the trip.