Robert Wedderburn was deeply influenced by his enslaved mother and grandmother, who raised him in Jamaica. After migrating to London, he became a key figure in ultraradical circles and was prosecuted by the British government for blasphemous libel. Wedderburn’s vision for abolition from below sought to forge a transatlantic alliance between English agrarian radicals and enslaved people in the Caribbean. Wedderburn’s influence was documented in Robert Cruikshank’s caricature, A Peep in the London Tavern, which depicted him challenging the proto-socialist Robert Owen. After a review of existing scholarship that places Wedderburn within ultraradical circles or focuses on his mixed-race identity, the Introduction argues that understanding Wedderburn’s advocacy for land-based insurrection requires dialogue with scholarship in Black geographies. Wedderburn’s insights about place-based resistance to slavery are then illustrated in a reading of James Hakewill’s Picturesque Tour of the Island of Jamaica.