Your total trip with all stops is around 1,270 miles / 2050 km, taking roughly 20 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 Waterloo, IA and Boston, MA.
Start from Waterloo, Iowa.
Chicago, Illinois is stopping point #1 after driving about 270 miles (430 km) or 4.5 hours.
Detroit, Michigan is stopping point #2 after driving about 280 miles (450 km) or 4.5 hours. Your total trip so far is about 550 miles or 880 km over roughly 9 hours of driving.
Buffalo, New York is stopping point #3 after driving about 270 miles (430 km) or 4 hours. Your total trip so far is about 820 miles or 1310 km over roughly 13 hours of driving.
Finally, Boston, Massachusetts is your destination after driving about 460 miles (740 km) or 7 hours. Your total trip with all stops is around 1,270 miles or 2050 km, taking roughly 20 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.