Old post but oh well. If you havent found out yet...there really isny much for wheeling in the southern part of wisconsin.
Best bets are to hook up with a group such as LCJs, CapCity 4x4, or Wisconsin 4x4 because they do a lot of wheeling on private property.
Otherwise there is the national forest and pipeline up north. Or if you go south there is Pittfsfield, The cliffs, and the badlands.