This agrarian geography of Kentucky begins on the streets of the state's largest city, in the throes of antiracist struggle. It tracks the state's lingering colonial settler power dynamics through the racism of plantation, extraction, and carceral geographies. It then traces how resistance to these exploitations take root in place-based agri-food initiatives unfolding through urban-rural solidarity against white supremacist policing, prison systems, labor exploitation, and extractivism. It begins with a brief overview of the scale of reference of Kentucky itself. Situating the state entails addressing the trauma and topophilia (love of landscape) of its agrarian past and present. It draws upon bell hooks’ literary invocations of Kentucky-based agrarian visions, as well as place-based political ecology scholarship (seven years of Kentucky Agrarian Questions practitioner panels at the Dimensions of Political Ecology Conference at University of Kentucky). Following Black and abolitionist geographies, this agrarian geography traces rural and urban shared struggles for food sovereignty, environmental justice, and liberation from racism of carceral systems. It introduces Kentucky grassroots projects connecting and uniting rural and urban struggles against carceral violence and the racism therein, such as Hood to the Holler (a political initiative emerging from Black Lives Matter mobilizations for Breonna Taylor). The essay ends with reflections on the political-ecological contradictions and imperative of working through and beyond a settler-colonial-state scale of reference like Kentucky. To extricate from and dismantle plantation modes and carceral legacies, abolitionist agrarian geographies recover the reality of Black and Indigenous agrarian history, presence, and futures. As such, rooted in place-based reckoning, resistance, and responsibility, they offer hope.