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Big Sandy River to Charlottesville

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Hi Fodorites!
I'm going to be driving from about 30 miles south of Ashland Kentucky along the Big Sandy River to Charlottesville VA. Never been to either place before or the Appalachians. Can anyone suggest good routes and things to see in between? I like good scenery, good music, friendly folks, small towns. I'm sort of planning to go over to the SW corner of VA now and then northward through various valleys. Good decision? Best roads?

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