Kentucky is an odd place, culturally speaking. I've lived and worked all over Kentucky (and the deep south--mostly Georgia) and I see it as being four different states culturally / geographically.
1) The triangle of Louisville, Covington, and Lexington is the bluegrass region. It's relatively upscale (compared to most of Kentucky), urban, and bent toward an odd mix of agriculture and commerce. I would not call it, culturally, southern.
2) Out east, say from Estill county to the border, is Appalachia. Mountain folk, their attitudes built by their rugged surroundings. Appalachian culture is completely distinct from southern culture. There was no antebellum period in, say, Pike County's history.
3) West Ky (where I currently live) feels like an offshoot of southern Indiana. The topography is totally different from the rest of the country (Corn, soybeans, and flat fields as far as the eye can see). Even the accents are a kind of nasal Southern Illinois accent.
4) The Cumberland Gap region (south central Kentucky) is part of southern culture. The lakes and rivers, the food, the speech, the general feel of the culture are all southern.
There you have it. Kentucky, one of the most culturally diverse states in the union.