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We are planning a trip from Connecticut to Memphis, Tennessee around Memorial Day. Rough idea is to visit West Virginia, Kentucky, Tennessee and back in about 5 days.
I don't know where in CT you are starting from. but it will probably be about 2500 miles round trip. If you like to DRIVE alot, it may not be too ambitious. But you won't have much time for sight-seeing. Given the distance you want to cover -- need to stick to interstate highways and zoom along. How much time you were figuring to spend in Memphis?