Ignore the naysayers in this thread, anon. They will make up any excuse to stay playing vidya in mom's basement and never venture out into the great unknown. That being said, the tremendous emptiness of America can be difficult to accept when you are alone. Even towns can seem so freaking devoid of life. You have to actively seek out people and break the ice; apart from rare instances where someone feels led by God to approach you, Americans aren't gonna come to you and intrude themselves into your life.

Remote resorts in Montana and Wyoming might be willing to hire a vagabond on the spot, now that college kids are going back to school. I recommend booking it straight out there from Wisconsin and making some money in the summer. Summer seasonal jobs are much more plentiful than winter seasonal jobs, and camping out is much more doable in the warmer months if you don't want to stay in the dirty employee dorm.