Your total trip with all stops is around 2,610 miles / 4210 km, taking roughly 39 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 Cheshire, CT and Caldwell, ID.
Start from Cheshire, Connecticut.
Scranton, Pennsylvania is stopping point #1 after driving about 170 miles (280 km) or 3 hours.
Cleveland, Ohio is stopping point #2 after driving about 370 miles (600 km) or 6 hours. Your total trip so far is about 550 miles or 880 km over roughly 8.5 hours of driving.
Chicago, Illinois is stopping point #3 after driving about 340 miles (550 km) or 5.5 hours. Your total trip so far is about 890 miles or 1430 km over roughly 14 hours of driving.
Des Moines, Iowa is stopping point #4 after driving about 330 miles (530 km) or 5 hours. Your total trip so far is about 1,220 miles or 1970 km over roughly 19 hours of driving.
Cheyenne, Wyoming is stopping point #5 after driving about 630 miles (1010 km) or 9 hours. Your total trip so far is about 1,850 miles or 2980 km over roughly 28 hours of driving.
Ogden, Utah is stopping point #6 after driving about 430 miles (700 km) or 6.5 hours. Your total trip so far is about 2,280 miles or 3680 km over roughly 34.5 hours of driving.
Finally, Caldwell, Idaho is your destination after driving about 330 miles (530 km) or 4.5 hours. Your total trip with all stops is around 2,610 miles or 4210 km, taking roughly 39 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.