Your total trip with all stops is around 1,890 miles / 3040 km, taking roughly 29.5 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 Cheyenne, WY and Springfield, MA.
Start from Cheyenne, Wyoming.
Lincoln, Nebraska is stopping point #1 after driving about 450 miles (720 km) or 6.5 hours.
Chicago, Illinois is stopping point #2 after driving about 520 miles (840 km) or 8.5 hours. Your total trip so far is about 970 miles or 1560 km over roughly 14.5 hours of driving.
Toledo, Ohio is stopping point #3 after driving about 250 miles (400 km) or 4 hours. Your total trip so far is about 1,210 miles or 1950 km over roughly 18.5 hours of driving.
Buffalo, New York is stopping point #4 after driving about 310 miles (490 km) or 5 hours. Your total trip so far is about 1,520 miles or 2440 km over roughly 23.5 hours of driving.
Finally, Springfield, Massachusetts is your destination after driving about 370 miles (600 km) or 5.5 hours. Your total trip with all stops is around 1,890 miles or 3040 km, taking roughly 29.5 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.