Douglass Park, Cherokee State Resort Park, Hensley Settlement, and Blue Heron represent parks in Kentucky with unique histories. Douglass and Cherokee State Resort Parks were established for African Americans during the era of legal segregation in the early 20th century. Hensley Settlement and Blue Heron became part of larger national parks after the founding communities abandoned them during the 1950s amid broader social and economic changes. Using archival imagery, maps, and recent aerial photography, this presentation explores these parks and their entangled boundaries between city and wilderness, public and private, and past and present.