Your total trip with all stops is around 1,120 miles / 1800 km, taking roughly 17.5 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 Jasper, AL and Cheshire, CT.
Start from Jasper, Alabama.
Chattanooga, Tennessee is stopping point #1 after driving about 190 miles (300 km) or 2.5 hours.
Roanoke, Virginia is stopping point #2 after driving about 370 miles (600 km) or 5.5 hours. Your total trip so far is about 560 miles or 900 km over roughly 8.5 hours of driving.
Washington, District of Columbia is stopping point #3 after driving about 240 miles (390 km) or 3.5 hours. Your total trip so far is about 800 miles or 1280 km over roughly 12 hours of driving.
New York, New York is stopping point #4 after driving about 230 miles (370 km) or 4 hours. Your total trip so far is about 1,030 miles or 1650 km over roughly 16 hours of driving.
Finally, Cheshire, Connecticut is your destination after driving about 90 miles (150 km) or 2 hours. Your total trip with all stops is around 1,120 miles or 1800 km, taking roughly 17.5 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.