Hydrogeologic investigations were conducted on the drainage systems of an area of the Pennyroyal sinkhole plain of south central Kentucky. The degree of karstification of five area streams was studied to develop an understanding of the evolution of drainage as the landscape changes from a sandstone caprock plateau to a limestone sinkhole plain. The Chester Upland, capped by the Big Clifty Sandstone, possesses predominantly surface drainage and the Pennyroyal Plain, formed on Mississippian limestones, possesses considerable subsurface drainage. As the Chester Upland Escarpment retreats and surface streams are onto the limestones, the streams evolve to become subsurface streams. The five streams observed in the study (all flowing on limestones) demonstrated less karst development close to the Chester Escarpment and more karst development with increasing distance from the escarpment. Sediments derived from the escarpment and plateau blanket the stream beds thus perching the streams and preventing chemically aggressive water from forming karst solution features in the limestones. The streams farther away from the escarpment are removed from the sediment source and are therefore able to downcut into the limestone and invade the subsurface to become cave streams. Lithologic investigation of limestones exposed in stream beds revealed that minor resistant units can act to diminish downcutting and maintain short sections of surface flow. The stream investigated was not flowing on a perching layer, but instead was held on the surface by a stratigraphic control (spillover layer) that prevented subterranean stream invasion. Dye traces conducted on groundwater flow in the sinkhole plain revealed that the area drainage pattern is changing as surface streams invade the subsurface and that integration between drainage basins is taking place. Stream piracy and stream diversion are occurring in the subsurface causing alteration of the existing topographic drainage divides that developed before the surface streams invaded the subsurface. A general model is presented which shows the evolution of surface drainage to subsurface drainage, as the Chester Escarpment continues its northwestward retreat.