KY 249 starts in the community of
Flippin, in western
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. 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 (US 31E Bus.) on the south side of Glasgow not too far from the Southgate Shopping Center and the
KY 63 junction. ==Major intersections==