There are literally only two things you need to do when doing an IAD skydiving jump. (This is assuming you chute doesn't decide it wants to kill you that day...) You need to turn the parachute so you don't hit anything like a power line, and right before you hit the ground, you need to flare your chute to slow down. I got the turning down fine. The second part not so much. It was epic and totally worth doing, just remember to flare your darn chute before you go smashing into a cornfield. :D I'm also an avid runner, and once convinced a friend to go on a two do 34 mile round trip run through a wolf and bear infested woods. It almost set a record low in August, and me and my friend shivered through the night trading off my emergency sleeping bag to stay alive. Worst part was that we never actually saw anything larger then a rabbit.

Milwaukee is pretty close. There's are loads of festivals and activities that go on in area. Plus there are a number of pretty cool hiking and biking trails.