Stopping points from Poughkeepsie, New York to Madison, Wisconsin:

• Start from Poughkeepsie, New York
• 2 hours to Scranton, Pennsylvania after driving about 120 miles / 190 km
• 6 hours to Cleveland, Ohio after driving about 370 miles / 600 km
• 2 hours to Toledo, Ohio after driving about 120 miles / 190 km
• 4 hours to Chicago, Illinois after driving about 250 miles / 390 km
• 2.5 hours to Madison, Wisconsin after driving about 150 miles / 240 km

Your total trip with all stops is around 1,000 miles / 1610 km, taking roughly 16 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 Poughkeepsie, NY and Madison, WI.

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Stopping points from Poughkeepsie, NY to Madison, WI

Start from Poughkeepsie, New York.

Scranton, Pennsylvania is stopping point #1 after driving about 120 miles (190 km) or 2 hours.

Cleveland, Ohio is stopping point #2 after driving about 370 miles (600 km) or 6 hours. Your total trip so far is about 490 miles or 790 km over roughly 8 hours of driving.

Toledo, Ohio is stopping point #3 after driving about 120 miles (190 km) or 2 hours. Your total trip so far is about 610 miles or 980 km over roughly 10 hours of driving.

Chicago, Illinois is stopping point #4 after driving about 250 miles (390 km) or 4 hours. Your total trip so far is about 850 miles or 1370 km over roughly 13.5 hours of driving.

Finally, Madison, Wisconsin is your destination after driving about 150 miles (240 km) or 2.5 hours. Your total trip with all stops is around 1,000 miles or 1610 km, taking roughly 16 hours for the whole trip.

Stopping point calculator

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.