The Tesla navigation app recommends driving from Duluth MN (begin with 80% charge) to the supercharger station at Minocqua, WI (166 miles) where the car will have 21% charge. A minimum charge time of 12 minutes will get you to Escanaba MI with 11% charge. Obviously, the longer one charges at Minocqua, the more battery charge upon arrival at Escanaba. The total distance of this route according to Google Maps is 310 miles (5 hrs, 48 min).
In comparison, the shortest distance by an ICE vehicle is 283 miles (5 hrs, 9 min). On this trip the gas car has a 30 mile or 40 minute advantage.
Just to demonstrate the conservative nature of the navigation app, even assuming a 100% charge in Duluth and a 300+ mile range, the app still recommends the Minocqua route.
Also keep in mind that one can buy a converter attachment that will allow a Tesla to use other EV charging stations that may be present along the shorter route.