Cultural mappings support a separate master plan commissioned by Cherokee Village (population: 4,900), a 23-square-mile rural planned community developed in 1955. The research describes the interconnectedness of landscapes, histories, and social geographies of the Arkansas Ozarks surrounding one of America’s first planned retirement‐based recreational communities. The series of 54 digital drawings integrates maps, folklore materials, archival sources, photographs, with new drawings, outlining five synchronic cultural frameworks that shaped Cherokee Village—Native American heritage, Ozark pioneer and folk heritage, camping and scouting, midcentury planned communities, and regional modernism in design and planning. Content development was a collaborative inquiry among residents, community organizations, artists, folklorists, historians, architects/landscape architects, and urban designers.