Your total trip with all stops is around 1,060 miles / 1710 km, taking roughly 16.5 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 Madison, WI and Springfield, MA.
Start from Madison, Wisconsin.
Chicago, Illinois is stopping point #1 after driving about 150 miles (240 km) or 2.5 hours.
Cleveland, Ohio is stopping point #2 after driving about 340 miles (550 km) or 5.5 hours. Your total trip so far is about 490 miles or 790 km over roughly 8 hours of driving.
Buffalo, New York is stopping point #3 after driving about 190 miles (310 km) or 3 hours. Your total trip so far is about 690 miles or 1100 km over roughly 11 hours of driving.
Finally, Springfield, Massachusetts is your destination after driving about 380 miles (600 km) or 5.5 hours. Your total trip with all stops is around 1,060 miles or 1710 km, taking roughly 16.5 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.