Your total trip with all stops is around 1,010 miles / 1620 km, taking roughly 15 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 Highlands Ranch, CO and Madison, WI.
Start from Highlands Ranch, Colorado.
North Platte, Nebraska is stopping point #1 after driving about 290 miles (460 km) or 4 hours.
Grand Island, Nebraska is stopping point #2 after driving about 140 miles (230 km) or 2 hours. Your total trip so far is about 430 miles or 690 km over roughly 6.5 hours of driving.
Omaha, Nebraska is stopping point #3 after driving about 150 miles (240 km) or 2 hours. Your total trip so far is about 580 miles or 930 km over roughly 8.5 hours of driving.
Des Moines, Iowa is stopping point #4 after driving about 140 miles (220 km) or 2 hours. Your total trip so far is about 710 miles or 1150 km over roughly 10.5 hours of driving.
Finally, Madison, Wisconsin is your destination after driving about 290 miles (470 km) or 4.5 hours. Your total trip with all stops is around 1,010 miles or 1620 km, taking roughly 15 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.