Your total trip with all stops is around 1,290 miles / 2070 km, taking roughly 19.5 hours for the whole trip. If you want to see every small town along the way, you can get a full list of cities between Portland, ME and Appleton, WI.
Start from Portland, Maine.
Springfield, Massachusetts is stopping point #1 after driving about 190 miles (310 km) or 3 hours.
Cleveland, Ohio is stopping point #2 after driving about 560 miles (890 km) or 8.5 hours. Your total trip so far is about 750 miles or 1200 km over roughly 11.5 hours of driving.
Chicago, Illinois is stopping point #3 after driving about 340 miles (550 km) or 5.5 hours. Your total trip so far is about 1,090 miles or 1750 km over roughly 16.5 hours of driving.
Finally, Appleton, Wisconsin is your destination after driving about 200 miles (310 km) or 3 hours. Your total trip with all stops is around 1,290 miles or 2070 km, taking roughly 19.5 hours for the whole trip.
Travelmath helps you figure out where to stop when planning a long road trip from one location to another. The best stopping point for an overnight hotel stay or a break from driving often depends on how far or how long you want to drive before pausing to rest. You can find the closest city to your stopping point to look for hotels, or explore other cities and towns along the route. Use this as a road trip planner when you're driving cross-country or mapping a route with multiple stops.