The black experience in Central Florida represents a critical node of imagination and activism. Influenced by the Booker T. Washington, communities such as Eatonville, the Parramore community in Orlando, or the historic Hannibal Square neighborhood in Winter Park represent important spaces to black agency in post-Reconstruction period. From education to enterprise, these communities featured collective and individual action to promote freedom. Recovering the history and ideology that shapes these communities requires a mixed methodology.