Brotherly Bonding Experience?

I've posted this once already and only got two responses, so here I am again. I need ideas for an all male trip, its me, 16 and my friend who has always been considered my older brother, Harry who is 22, I have no idea what to do, down to the basic outline of the trip. I want to make it special. We are pretty open to anything. We live about 4 or so hours outside of Chicago, so we are open to traveling