Your total trip with all stops is around 1,950 miles / 3140 km, taking roughly 29.5 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 Springfield, OR and Winona, MN.
Start from Springfield, Oregon.
Spokane, Washington is stopping point #1 after driving about 460 miles (750 km) or 7.5 hours.
Missoula, Montana is stopping point #2 after driving about 200 miles (320 km) or 3 hours. Your total trip so far is about 660 miles or 1060 km over roughly 10.5 hours of driving.
Billings, Montana is stopping point #3 after driving about 350 miles (560 km) or 5 hours. Your total trip so far is about 1,010 miles or 1620 km over roughly 15.5 hours of driving.
Rapid City, South Dakota is stopping point #4 after driving about 320 miles (520 km) or 5 hours. Your total trip so far is about 1,330 miles or 2140 km over roughly 20.5 hours of driving.
Sioux Falls, South Dakota is stopping point #5 after driving about 350 miles (560 km) or 5 hours. Your total trip so far is about 1,680 miles or 2700 km over roughly 25 hours of driving.
Finally, Winona, Minnesota is your destination after driving about 280 miles (450 km) or 4 hours. Your total trip with all stops is around 1,950 miles or 3140 km, taking roughly 29.5 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.