This dissertation uses “Derby Cruising” in order to open up the tension between African Americans in Louisville and the Kentucky Derby Festival, especially as that tension was manifest in the spaces of West Louisville. The Kentucky Derby Festival has long served as a site of mediation between people of color and official Louisville. Derby Cruising (1998-2005) and protests around the open housing movement (1967) and anti-police violence (2000) are presented as three critical sites where African American expressions of identity, representation, and belonging have been negotiated through the Kentucky Derby Festival at particular historical moments and in particular places in the city. The dissertation assumes the place of these negotiations in the politics of racialization processes. It employs theories of “festival” and “carnival” inspired by the work of Bahktin, Hall, Nurse, and others in order to conceptualize transgression, protest, and community representation and highlights the importance of festival times as a critical opportunity for marginalized populations to assert a political voice, especially within African American communities. The cases are presented with information drawn from interviews with West Louisville residents, community leaders, and other affiliated officials, as well as from newspaper, media and archival sources.