Should I be worried about black bears near my property?

i also live in wisconsin, i dont think it is a huge issue having the bears there. As long as your house is locked up tight you should be fine until they move elsewhere. For your apple picking, make sure you can see the bears at all times, and if they start to approach at all, make sure you have a plan of "escape" because the nature is unpredictible. If you start to feel uncomfortable at home or being outside, you could always contact the DNR. Black Bears are afraid of loud noises and typically run, if you are in between their cub, that will not do anything. More than likley tthey will try and get rid of the threat (you). Maybe if it is possible, you could have a DNR worker come and stay when you harvest the apples.