Your total trip with all stops is around 1,720 miles / 2770 km, taking roughly 27 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 Enid, OK and Lexington, MA.
Start from Enid, Oklahoma.
Springfield, Missouri is stopping point #1 after driving about 300 miles (470 km) or 4.5 hours.
Saint Louis, Missouri is stopping point #2 after driving about 220 miles (350 km) or 3.5 hours. Your total trip so far is about 510 miles or 820 km over roughly 8 hours of driving.
Indianapolis, Indiana is stopping point #3 after driving about 240 miles (390 km) or 3.5 hours. Your total trip so far is about 760 miles or 1220 km over roughly 11.5 hours of driving.
Cleveland, Ohio is stopping point #4 after driving about 320 miles (510 km) or 5 hours. Your total trip so far is about 1,070 miles or 1730 km over roughly 16.5 hours of driving.
Rochester, New York is stopping point #5 after driving about 260 miles (420 km) or 4 hours. Your total trip so far is about 1,330 miles or 2140 km over roughly 20.5 hours of driving.
Finally, Lexington, Massachusetts is your destination after driving about 390 miles (630 km) or 6.5 hours. Your total trip with all stops is around 1,720 miles or 2770 km, taking roughly 27 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.