This dissertation considers the role biography can play in analyses of past landscapes and, conversely, how those landscapes can help us better understand the lives of individuals. It focuses on one person, David Ruggles—a blind, African American, journalist, doctor, businessman, and antislavery activist—and a specific landscape, that of western Massachusetts during the mid-19th century. The questions that guide this dissertation concern the extent to which understanding past landscapes can reveal the previously unconsidered dimensions of the lives of people who experienced them. The landscape is considered through multiple scales in this dissertation. It draws on historical research as well as the modern-day Florence, Massachusetts landscape to reveal how Ruggles\u27 experience was mediated by his race, physical ability, and social position. It also incorporates ethnographic data obtained from questionnaires and in-depth interviews to interrogate the role knowledge of local history plays in contemporary life. This research makes important methodological contributions to the field of historical archaeology. First, it demonstrates the utility of a biographical approach to analyses of the landscape and the past. Second, it highlights a dimension of the human past that is often overlooked in historical archaeology: the lives of people with disabilities. Third, in considering the life of a blind man, it recognizes that the landscape is experienced multi-sensorily and, furthermore, that the experience of walking through the landscape implicates one in a multitude of socio-historical processes that alter the landscape and influence the circumstances in which people interact. Finally, the ethnographic data reveal how knowledge about historical landscapes and the people who inhabited them come to be combined with contemporary experiences and interests to create new meanings and understandings