Monroe County borders Tennessee and is centered on Tompkinsville. Known for Dale Hollow Lake access, affordable mountain-edge farmland, and a close-knit community with deep agricultural roots. Discover authentic Appalachian living in Owsley County, an Eastern Kentucky treasure with Booneville as its county seat. Home to a small population of just over 4,400, this county offers rugged, heavily wooded land, perfect for those seeking ultimate privacy, self-sufficiency, and a connection to unspoiled natural beauty.