Kentucky Route 249Kentucky Route 249 is a north–south state highway that traverses two counties in South Central Kentucky.Route descriptionKY 249 starts in the community of Flippin, in western Monroe [County, Kentucky|Monroe County], at an intersection with KY 100. Almost immediately after its start, KY 249 intersects KY 678. It makes its way into Barren County a few miles later and goes through mainly rural areas of Barren County, including the community of Roseville, [Barren County, Kentucky|Roseville]. Once it reaches Glasgow, it crosses the Louie B. Nunn Cumberland Expressway via an overpass, and reaches its northern end at a junction with U.S. Route 31E Business on the south side of Glasgow not too far from the Southgate Shopping Center and the KY 63 junction.