Red Rider,
I really feel for you. I grew up in SE Wisconsin and I had my first overnight rides around your age.
Does your mom know about safe trails like the Glacial Drumlin trail (Waukesha almost to Madison), the Military Ridge Trail, the Elroy to Sparta Trail, and the light roads that connect them? Wisconsin is one of the best connected states for small safe trails. Check these trails (just an example of what there is in Wisconsin. Wisconsin is one of the best bicycling states.)
Howard