Your total trip with all stops is around 2,770 miles / 4460 km, taking roughly 42.5 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 Richland, WA and Poughkeepsie, NY.
Start from Richland, Washington.
Missoula, Montana is stopping point #1 after driving about 340 miles (550 km) or 5.5 hours.
Billings, Montana is stopping point #2 after driving about 340 miles (550 km) or 5 hours. Your total trip so far is about 690 miles or 1100 km over roughly 10.5 hours of driving.
Dickinson, North Dakota is stopping point #3 after driving about 320 miles (510 km) or 4.5 hours. Your total trip so far is about 1,000 miles or 1610 km over roughly 15 hours of driving.
Fargo, North Dakota is stopping point #4 after driving about 290 miles (470 km) or 4 hours. Your total trip so far is about 1,290 miles or 2080 km over roughly 19 hours of driving.
Minneapolis, Minnesota is stopping point #5 after driving about 240 miles (380 km) or 3.5 hours. Your total trip so far is about 1,530 miles or 2460 km over roughly 22.5 hours of driving.
Chicago, Illinois is stopping point #6 after driving about 410 miles (660 km) or 6 hours. Your total trip so far is about 1,940 miles or 3120 km over roughly 29 hours of driving.
Cleveland, Ohio is stopping point #7 after driving about 340 miles (550 km) or 5.5 hours. Your total trip so far is about 2,280 miles or 3670 km over roughly 34.5 hours of driving.
Finally, Poughkeepsie, New York is your destination after driving about 490 miles (780 km) or 8 hours. Your total trip with all stops is around 2,770 miles or 4460 km, taking roughly 42.5 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.