Your total trip with all stops is around 980 miles / 1580 km, taking roughly 17 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 Winkler, Canada and Aurora, CO.
Start from Winkler, Manitoba.
Jamestown, North Dakota is stopping point #1 after driving about 190 miles (310 km) or 3 hours.
North Platte, Nebraska is stopping point #2 after driving about 530 miles (840 km) or 10 hours. Your total trip so far is about 720 miles or 1160 km over roughly 13.5 hours of driving.
Finally, Aurora, Colorado is your destination after driving about 260 miles (420 km) or 3.5 hours. Your total trip with all stops is around 980 miles or 1580 km, taking roughly 17 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.