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I didn't add any other eastern Kentucky cities--London, Corbin, Middlesboro, Pikeville, Paintsville, Maysville, Mt. Sterling--because they just aren't very large. Ashland has under 21,000 people and, other than Richmond (pop. 30,000), it is the largest city in eastern Kentucky.
If anyone can make some good arguments for EKY, they won't be ignored (or criticized.)
Oh yeah, while I wouldn't include these in my favorite cities, they are small cities with some good things to offer.
1. Madisonville: very nice healthcare system for such a small town, growing at a moderately-slow but healthy rate.
2. Shelbyville: impressive arts scene for such a small town, there has been talk of converting Main St. in downtown S'ville into a sort of "Arts corridor." Shelby Co. Community Theatre already has a permenant building there.
My vote is Morehead, which is not on your list. I now live in PA but went to Morehead State University from 1967-71 and fell in love with the area. Living in a dry county and going with my buddies to Mt. Sterling for a drink. Or maybe just going to the bootleggers at the end of town. By the way is Roger Dillow out there? We were friends back then, this is Murphy talking.
I live in Morehead now and love every minute of it. Very small town... growing a tiny bit.... MSU and the mountains are great. Friendly people, in the foothills of the Appalachians, one hour from Lexington or Huntington and only 10 miles or less from Cave Run Lake... great town, any way you look at it! Sorry, just moved here recently Otis "Murphy" so don't know any locals, but if I remember to, I'll ask my land lady Pat Dailey. I believe she grew up here and knows about anyone there is to know....
Owensboro is, once again, on the verge of a possible boom. Arts are VERY high, AND there is renewed action by a fairly progressive city management on the building of an Interstate (I-69) which would cement a huge growth in the next 10 years. Already, the city (and Daviess County) are seeing a larger than US average in population growth in the past 3 years. But, I was shocked to learn even Greyhound doesn't go there anymore. That'll change, and folks who move in now will be glad they did.
Lexington is just the "hippest" place in the south - very reminiscent of a sprawling Midtown Atlanta, without the traffic, crime, racial unbalance, and soaring cost of living. Clean, friendly, everything Evansville, IN wants to be.
I like Paris, Manchester, London. Bybee, and I voted for Richmond/
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