Your total trip with all stops is around 1,050 miles / 1690 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 Greenfield, WI and Leominster, MA.
Start from Greenfield, Wisconsin.
South Bend, Indiana is stopping point #1 after driving about 150 miles (240 km) or 2.5 hours.
Cleveland, Ohio is stopping point #2 after driving about 260 miles (410 km) or 4 hours. Your total trip so far is about 410 miles or 660 km over roughly 6.5 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 600 miles or 970 km over roughly 9.5 hours of driving.
Syracuse, New York is stopping point #4 after driving about 150 miles (250 km) or 2.5 hours. Your total trip so far is about 750 miles or 1210 km over roughly 12 hours of driving.
Finally, Leominster, Massachusetts is your destination after driving about 300 miles (470 km) or 5 hours. Your total trip with all stops is around 1,050 miles or 1690 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.