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I went from Madison west to the Black Hills, and stayed in Rapid City, S.D. I had been there before, and was eager to get back. You go through some really funky country in the Badlands. Don't miss the Corn Palace in Mitchell, S.D. -- an arena made out of corn. If Madison still has sticky summer weather, you'll leave that behind in the Black Hills, where it will be pleasant and dry. Mount Rushmore is kind of an underrated attraction, IMO. And the Black Hills are mountains, not hills. It's kind of a miniature Rockies.
From Rapid City you can go up to Sturgis (just missed the epic motorcycle extravaganza), to Little Big Horn in Montana. I think the area is worth several days. Rapid City had some hopping little nightspots ten years ago. But if you get bored in Rapid City, Denver is less than a day's drive away.
The only other option I see coming out of Madison for a short time is go to Chicago and party.