Surely from an "American HIstory" perspective, given that (at least when we think of the human population) the vast majority of this history was from 13,000 BCE to 1000 CE (more or less). During this period settlement was from Alaska east and south, with people arriving in the southernmost parts of the continent somewhat later. Kentucky would have been some millenia after arrival in Alaska, so once populated would have been "East" or "Southeast"... at least for a few millenia.