Your total trip with all stops is around 1,870 miles / 3010 km, taking roughly 28 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 Longview, WA and Winona, MN.
Start from Longview, Washington.
Spokane, Washington is stopping point #1 after driving about 390 miles (620 km) or 5.5 hours.
Missoula, Montana is stopping point #2 after driving about 200 miles (320 km) or 3 hours. Your total trip so far is about 590 miles or 940 km over roughly 9 hours of driving.
Billings, Montana is stopping point #3 after driving about 340 miles (550 km) or 5 hours. Your total trip so far is about 930 miles or 1490 km over roughly 14 hours of driving.
Rapid City, South Dakota is stopping point #4 after driving about 320 miles (510 km) or 5 hours. Your total trip so far is about 1,240 miles or 2000 km over roughly 19 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 1,590 miles or 2560 km over roughly 24 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 1,870 miles or 3010 km, taking roughly 28 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.