GIS modeling and analysis of multispectral satellite imagery are applied to a former plantation in the British Virgin Islands (BVI), which, in 1831, became a settlement of free Africans who lived within slavery-based British colonialism. A map of the settlement represents the paternalist British government ideal for this community—an “experiment” for controlling a postemancipation peasantry—and the techniques discussed here allow clearer understanding of the way these ideals would have interacted with the physical and social landscape of the BVI had they been implemented. The residents were certainly aware of their situation, and this study does not mean to imply that they simply adopted the plan they were handed. Instead, our goal is to interrogate the implications of the plan itself. We combine least cost path (LCP), Normalized Difference Vegetation Indexes (NDVI), and other technical analyses to show the interaction of the British plan and the BVI landscape in order to describe the context in which the Kingstown community was built and maintained. Although schematic, this study quantifies at least some of the barriers the community overcame and contributes in a limited way to broader considerations of the place of land and landscape in structures of colonialism.