Could you drive from Wisconsin to Michigan without crossing another state? If yes, how? If no, why not?
Yes. You'd drive from Wisconsin into Michigan's U.P.
http://www.medcitynews.com/wordpress/wp-content/uploads/michigan-map.jpg
Yes
No, it is not possible to drive from Wisconsin to Michigan without crossing another state. Both Wisconsin and Michigan share a common border with Lake Michigan, which would need to be crossed to reach the other state. Therefore, it is necessary to drive through either Illinois or Indiana to reach Michigan from Wisconsin by road.
To confirm this, you can use various mapping services or GPS applications such as Google Maps, Apple Maps, or MapQuest. Simply enter the starting location as a city in Wisconsin (e.g., Milwaukee) and the destination as a city in Michigan (e.g., Detroit). The suggested route will include driving through either Illinois or Indiana.