Your total trip with all stops is around 2,760 miles / 4440 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 Kennewick, WA and Poughkeepsie, NY.
Start from Kennewick, Washington.
Missoula, Montana is stopping point #1 after driving about 340 miles (540 km) or 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 680 miles or 1090 km over roughly 10 hours of driving.
Rapid City, South Dakota is stopping point #3 after driving about 320 miles (510 km) or 5 hours. Your total trip so far is about 1,000 miles or 1600 km over roughly 15.5 hours of driving.
Sioux Falls, South Dakota is stopping point #4 after driving about 350 miles (560 km) or 5 hours. Your total trip so far is about 1,340 miles or 2160 km over roughly 20 hours of driving.
Rochester, Minnesota is stopping point #5 after driving about 240 miles (380 km) or 3.5 hours. Your total trip so far is about 1,580 miles or 2540 km over roughly 23.5 hours of driving.
Chicago, Illinois is stopping point #6 after driving about 350 miles (560 km) or 5.5 hours. Your total trip so far is about 1,930 miles or 3110 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 2,270 miles or 3660 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 2,760 miles or 4440 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.