Your total trip with all stops is around 1,070 miles / 1720 km, taking roughly 18 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 Hilton Head Island, SC and Dennis, MA.
Start from Hilton Head Island, South Carolina.
Fayetteville, North Carolina is stopping point #1 after driving about 260 miles (410 km) or 4 hours.
Richmond, Virginia is stopping point #2 after driving about 210 miles (340 km) or 3 hours. Your total trip so far is about 470 miles or 750 km over roughly 7 hours of driving.
Philadelphia, Pennsylvania is stopping point #3 after driving about 250 miles (400 km) or 4 hours. Your total trip so far is about 710 miles or 1150 km over roughly 11 hours of driving.
Finally, Dennis, Massachusetts is your destination after driving about 350 miles (570 km) or 7 hours. Your total trip with all stops is around 1,070 miles or 1720 km, taking roughly 18 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.