Stopping points from Cheshire, Connecticut to Anchorage, Alaska:

• Start from Cheshire, Connecticut
• 8.5 hours to Cleveland, Ohio after driving about 540 miles / 880 km
• 5.5 hours to Chicago, Illinois after driving about 340 miles / 550 km
• 6 hours to Minneapolis, Minnesota after driving about 410 miles / 660 km
• 7.5 hours to Minot, North Dakota after driving about 500 miles / 800 km
• 11.5 hours to Edmonton, Canada after driving about 730 miles / 1170 km
• 4.5 hours to Grande Prairie, Canada after driving about 290 miles / 460 km
• 13.5 hours to Watson Lake, Canada after driving about 680 miles / 1100 km
• 5.5 hours to Whitehorse, Canada after driving about 270 miles / 440 km
• 13 hours to Anchorage, Alaska after driving about 710 miles / 1130 km

Your total trip with all stops is around 4,470 miles / 7190 km, taking roughly 75.5 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 Cheshire, CT and Anchorage, AK.

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Stopping points from Cheshire, CT to Anchorage, AK

Start from Cheshire, Connecticut.

Cleveland, Ohio is stopping point #1 after driving about 540 miles (880 km) or 8.5 hours.

Chicago, Illinois is stopping point #2 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.

Minneapolis, Minnesota is stopping point #3 after driving about 410 miles (660 km) or 6 hours. Your total trip so far is about 1,300 miles or 2090 km over roughly 20 hours of driving.

Minot, North Dakota is stopping point #4 after driving about 500 miles (800 km) or 7.5 hours. Your total trip so far is about 1,800 miles or 2890 km over roughly 27.5 hours of driving.

Edmonton, Canada is stopping point #5 after driving about 730 miles (1170 km) or 11.5 hours. Your total trip so far is about 2,530 miles or 4060 km over roughly 39 hours of driving.

Grande Prairie, Canada is stopping point #6 after driving about 290 miles (460 km) or 4.5 hours. Your total trip so far is about 2,810 miles or 4520 km over roughly 44 hours of driving.

Watson Lake, Canada is stopping point #7 after driving about 680 miles (1100 km) or 13.5 hours. Your total trip so far is about 3,490 miles or 5620 km over roughly 57 hours of driving.

Whitehorse, Canada is stopping point #8 after driving about 270 miles (440 km) or 5.5 hours. Your total trip so far is about 3,770 miles or 6060 km over roughly 62.5 hours of driving.

Finally, Anchorage, Alaska is your destination after driving about 710 miles (1130 km) or 13 hours. Your total trip with all stops is around 4,470 miles or 7190 km, taking roughly 75.5 hours for the whole trip.

Stopping point calculator

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.