Your total trip with all stops is around 700 miles / 1130 km, taking roughly 12.5 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 YWG and Keystone, SD.
Start from Winnipeg James Armstrong Richardson International Airport.
Killarney, Canada is stopping point #1 after driving about 160 miles (250 km) or 3.5 hours.
Bismarck, North Dakota is stopping point #2 after driving about 230 miles (370 km) or 4 hours. Your total trip so far is about 380 miles or 620 km over roughly 7.5 hours of driving.
Finally, Keystone, South Dakota is your destination after driving about 320 miles (510 km) or 5 hours. Your total trip with all stops is around 700 miles or 1130 km, taking roughly 12.5 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.