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

• Start from Madison, Wisconsin
• 2.5 hours to Chicago, Illinois after driving about 150 miles / 240 km
• 4 hours to Toledo, Ohio after driving about 250 miles / 390 km
• 2 hours to Akron, Ohio after driving about 140 miles / 220 km
• 6 hours to Scranton, Pennsylvania after driving about 350 miles / 570 km
• 2 hours to Poughkeepsie, New York after driving about 110 miles / 180 km

Your total trip with all stops is around 1,000 miles / 1600 km, taking roughly 16.5 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 Madison, WI and Poughkeepsie, NY.

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Stopping points from Madison, WI to Poughkeepsie, NY

Start from Madison, Wisconsin.

Chicago, Illinois is stopping point #1 after driving about 150 miles (240 km) or 2.5 hours.

Toledo, Ohio is stopping point #2 after driving about 250 miles (390 km) or 4 hours. Your total trip so far is about 390 miles or 630 km over roughly 6.5 hours of driving.

Akron, Ohio is stopping point #3 after driving about 140 miles (220 km) or 2 hours. Your total trip so far is about 530 miles or 850 km over roughly 8.5 hours of driving.

Scranton, Pennsylvania is stopping point #4 after driving about 350 miles (570 km) or 6 hours. Your total trip so far is about 880 miles or 1420 km over roughly 14.5 hours of driving.

Finally, Poughkeepsie, New York is your destination after driving about 110 miles (180 km) or 2 hours. Your total trip with all stops is around 1,000 miles or 1600 km, taking roughly 16.5 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.