This dissertation uses the tools of historical Geographic Information Systems (hGIS) to locate and describe mid-nineteenth-century plantation landscapes in Talbot County, Maryland. The methodology described here combines historic maps, historic and modern aerial photography, LiDAR-derived elevation data, historic census data, and textual descriptions. It also uses them in conjunction with an ongoing archaeological research project at Wye House, the ancestral seat of the Lloyd family and site of enslavement of Frederick Douglass, near Easton, Maryland in order to further develop ways for archaeologists, historians, and other researchers to work with cartographic and spatial data in a digital framework. This methodology can be used across multiple scales to survey remotely individual sites or even entire counties for potential archaeological resources. Furthermore, it examines the autobiographies of Frederick Douglass, not only because he was a witness to these landscapes, but also because he can be read as a social theorist who addresses issues of race and racialized landscapes throughout his writings. Lastly, it uses these sources of data to consider Dell Upton’s spatial hypothesis regarding racialized plantation landscapes. Taken together, this study of mid-nineteenth-century Talbot County, Maryland represents one way to identify and recover lost sites of African American heritage that would otherwise remain lost.