Your total trip with all stops is around 2,900 miles / 4670 km, taking roughly 44.5 hours for the whole trip.
Start from Simi Valley, California.
Las Vegas, Nevada is stopping point #1 after driving about 300 miles (490 km) or 4.5 hours.
Grand Junction, Colorado is stopping point #2 after driving about 510 miles (810 km) or 7.5 hours. Your total trip so far is about 810 miles or 1300 km over roughly 12 hours of driving.
Denver, Colorado is stopping point #3 after driving about 240 miles (390 km) or 4 hours. Your total trip so far is about 1,050 miles or 1690 km over roughly 15.5 hours of driving.
Grand Island, Nebraska is stopping point #4 after driving about 400 miles (650 km) or 6 hours. Your total trip so far is about 1,460 miles or 2340 km over roughly 21.5 hours of driving.
Chicago, Illinois is stopping point #5 after driving about 610 miles (990 km) or 9.5 hours. Your total trip so far is about 2,070 miles or 3330 km over roughly 30.5 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 2,410 miles or 3880 km over roughly 36 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 2,900 miles or 4670 km, taking roughly 44.5 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.