Your total trip with all stops is around 1,050 miles / 1690 km, taking roughly 16.5 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 Winona, MN and Baltimore, MD.
Start from Winona, Minnesota.
Milwaukee, Wisconsin is stopping point #1 after driving about 230 miles (370 km) or 3.5 hours.
Cleveland, Ohio is stopping point #2 after driving about 440 miles (700 km) or 7 hours. Your total trip so far is about 670 miles or 1080 km over roughly 10.5 hours of driving.
Pittsburgh, Pennsylvania is stopping point #3 after driving about 140 miles (220 km) or 2 hours. Your total trip so far is about 800 miles or 1290 km over roughly 12.5 hours of driving.
Finally, Baltimore, Maryland is your destination after driving about 250 miles (400 km) or 4 hours. Your total trip with all stops is around 1,050 miles or 1690 km, taking roughly 16.5 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.