Your total trip with all stops is around 760 miles / 1220 km, taking roughly 13 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 GCC and YWG.
Start from Gillette-Campbell County Airport.
Dickinson, North Dakota is stopping point #1 after driving about 260 miles (420 km) or 4.5 hours.
Brandon, Canada is stopping point #2 after driving about 350 miles (560 km) or 6 hours. Your total trip so far is about 610 miles or 980 km over roughly 10.5 hours of driving.
Finally, Winnipeg James Armstrong Richardson International Airport is your destination after driving about 150 miles (230 km) or 2.5 hours. Your total trip with all stops is around 760 miles or 1220 km, taking roughly 13 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.