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Eastern Kentucky is a "big small" place. I mean that the eastern 2/5 of Kentucky is a vast expanse of hills and forests, basically. Don't get me wrong, I like hiking, but I find many hillsides in eastern Ky. to be litter-covered, so that coupled with high gas prices prompts me to hike closer to home here in central Kentucky.
Anyway, a "big" town might be Pikeville (pop. 6,300), Middlesboro (pop. 10,500), or the largest city in eastern Ky., Ashland (pop. 21,000). All of these are still very small towns. The only metropolitan area with any presence in eastern Kentucky is the Huntington MSA, which expands into three RURAL eastern Ky. counties.
If you love hiking, you can try Red River Gorge or Natural Bridge State Resort Park, which has a nice lodge. Visit the Colonel Sanders Cafe and Cumberland Falls State Resort Park, in and near Corbin, respectively. Cumberland Gap National Historical Park is supposedly where Daniel Boone hiked through to enter the new frontier, Kentucky.
Apart from these things, there's not much to offer east of I-75. Sorry.
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