Your total trip with all stops is around 1,310 miles / 2110 km, taking roughly 20 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 Roswell, NM.
Start from Madison, Wisconsin.
Des Moines, Iowa is stopping point #1 after driving about 290 miles (470 km) or 4.5 hours.
Kansas City, Missouri is stopping point #2 after driving about 190 miles (310 km) or 3 hours. Your total trip so far is about 490 miles or 780 km over roughly 7.5 hours of driving.
Oklahoma City, Oklahoma is stopping point #3 after driving about 350 miles (570 km) or 5 hours. Your total trip so far is about 840 miles or 1350 km over roughly 12.5 hours of driving.
Finally, Roswell, New Mexico is your destination after driving about 470 miles (760 km) or 7.5 hours. Your total trip with all stops is around 1,310 miles or 2110 km, taking roughly 20 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.