Your total trip with all stops is around 2,970 miles / 4780 km, taking roughly 45.5 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 Portland, OR and Poughkeepsie, NY.
Start from Portland, Oregon.
Boise, Idaho is stopping point #1 after driving about 430 miles (690 km) or 6.5 hours.
Ogden, Utah is stopping point #2 after driving about 310 miles (500 km) or 4.5 hours. Your total trip so far is about 740 miles or 1190 km over roughly 11 hours of driving.
Cheyenne, Wyoming is stopping point #3 after driving about 440 miles (700 km) or 6.5 hours. Your total trip so far is about 1,170 miles or 1890 km over roughly 17.5 hours of driving.
Lincoln, Nebraska is stopping point #4 after driving about 440 miles (710 km) or 6.5 hours. Your total trip so far is about 1,620 miles or 2600 km over roughly 24 hours of driving.
Chicago, Illinois is stopping point #5 after driving about 520 miles (840 km) or 8 hours. Your total trip so far is about 2,140 miles or 3440 km over roughly 32 hours of driving.
Cleveland, Ohio is stopping point #6 after driving about 340 miles (550 km) or 5.5 hours. Your total trip so far is about 2,480 miles or 3990 km over roughly 37.5 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 2,970 miles or 4780 km, taking roughly 45.5 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.