Sleepy Hollow Country Club in Cumberland, Kentucky, is a private course designed by Michael Gleason. The layout reflects Gleason's approach to routing and design, integrating the natural topography and landscape character of the region. The course plays through a mix of wooded terrain and open areas typical of eastern Kentucky's rolling geography, with strategic bunkering and water features that define the playing corridors. The routing takes advantage of the site's natural elevation changes, creating variety in hole character and shot-making demands across the eighteen holes. Gleason's design emphasizes playability alongside strategic challenge, with greens complexes that reward accuracy and course management. The course has developed a reputation within regional golf circles as a solid test that balances accessibility for members of varying skill levels with enough complexity to engage accomplished players. As a private country club, Sleepy Hollow serves its membership with golf as a central amenity alongside the broader club experience. The setting and membership base reflect Cumberland's character as a regional community, with the course functioning as a social and recreational anchor for the club. The design has proven durable and well-suited to its landscape, maintaining relevance within the competitive context of regional private courses in Kentucky.