Your total trip with all stops is around 920 miles / 1490 km, taking roughly 14.5 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 Spring Valley, NY and Milwaukee, WI.
Start from Spring Valley, New York.
Williamsport, Pennsylvania is stopping point #1 after driving about 190 miles (300 km) or 3 hours.
Cleveland, Ohio is stopping point #2 after driving about 290 miles (460 km) or 4.5 hours. Your total trip so far is about 470 miles or 760 km over roughly 7.5 hours of driving.
Toledo, Ohio is stopping point #3 after driving about 120 miles (190 km) or 2 hours. Your total trip so far is about 590 miles or 950 km over roughly 9.5 hours of driving.
Finally, Milwaukee, Wisconsin is your destination after driving about 340 miles (540 km) or 5.5 hours. Your total trip with all stops is around 920 miles or 1490 km, taking roughly 14.5 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.