Your total trip with all stops is around 2,090 miles / 3360 km, taking roughly 31.5 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 Corvallis, OR and Madison, WI.
Start from Corvallis, Oregon.
Spokane, Washington is stopping point #1 after driving about 440 miles (700 km) or 7 hours.
Billings, Montana is stopping point #2 after driving about 540 miles (870 km) or 8 hours. Your total trip so far is about 980 miles or 1570 km over roughly 15 hours of driving.
Dickinson, North Dakota is stopping point #3 after driving about 320 miles (510 km) or 4.5 hours. Your total trip so far is about 1,290 miles or 2080 km over roughly 20 hours of driving.
Fargo, North Dakota is stopping point #4 after driving about 290 miles (470 km) or 4 hours. Your total trip so far is about 1,590 miles or 2550 km over roughly 24 hours of driving.
Minneapolis, Minnesota is stopping point #5 after driving about 240 miles (380 km) or 3.5 hours. Your total trip so far is about 1,820 miles or 2930 km over roughly 27.5 hours of driving.
Finally, Madison, Wisconsin is your destination after driving about 270 miles (430 km) or 4 hours. Your total trip with all stops is around 2,090 miles or 3360 km, taking roughly 31.5 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.