Your total trip with all stops is around 1,850 miles / 2970 km, taking roughly 28.5 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 Conroe, TX and Milford, MA.
Start from Conroe, Texas.
Baton Rouge, Louisiana is stopping point #1 after driving about 280 miles (440 km) or 4.5 hours.
Birmingham, Alabama is stopping point #2 after driving about 400 miles (640 km) or 6 hours. Your total trip so far is about 670 miles or 1080 km over roughly 10.5 hours of driving.
Knoxville, Tennessee is stopping point #3 after driving about 260 miles (410 km) or 3.5 hours. Your total trip so far is about 930 miles or 1500 km over roughly 14 hours of driving.
Roanoke, Virginia is stopping point #4 after driving about 260 miles (420 km) or 4 hours. Your total trip so far is about 1,190 miles or 1910 km over roughly 18 hours of driving.
New York, New York is stopping point #5 after driving about 460 miles (740 km) or 7 hours. Your total trip so far is about 1,650 miles or 2650 km over roughly 25 hours of driving.
Finally, Milford, Massachusetts is your destination after driving about 200 miles (320 km) or 3.5 hours. Your total trip with all stops is around 1,850 miles or 2970 km, taking roughly 28.5 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.