Your total trip with all stops is around 1,240 miles / 2000 km, taking roughly 19.5 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 Melbourne, FL and Cheshire, CT.
Start from Melbourne, Florida.
Jacksonville, Florida is stopping point #1 after driving about 180 miles (280 km) or 2.5 hours.
Raleigh, North Carolina is stopping point #2 after driving about 450 miles (730 km) or 6.5 hours. Your total trip so far is about 630 miles or 1010 km over roughly 9 hours of driving.
Philadelphia, Pennsylvania is stopping point #3 after driving about 420 miles (670 km) or 6.5 hours. Your total trip so far is about 1,050 miles or 1680 km over roughly 15.5 hours of driving.
Finally, Cheshire, Connecticut is your destination after driving about 200 miles (310 km) or 4 hours. Your total trip with all stops is around 1,240 miles or 2000 km, taking roughly 19.5 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.