Your total trip with all stops is around 940 miles / 1510 km, taking roughly 16 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 Massachusetts and Kentucky.
Start from Massachusetts (MA).
New York, New York is stopping point #1 after driving about 200 miles (310 km) or 4 hours.
Morgantown, West Virginia is stopping point #2 after driving about 380 miles (610 km) or 6.5 hours. Your total trip so far is about 570 miles or 920 km over roughly 10.5 hours of driving.
Charleston, West Virginia is stopping point #3 after driving about 160 miles (250 km) or 2.5 hours. Your total trip so far is about 730 miles or 1170 km over roughly 12.5 hours of driving.
Finally, Kentucky (KY) is your destination after driving about 210 miles (340 km) or 3.5 hours. Your total trip with all stops is around 940 miles or 1510 km, taking roughly 16 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.