Literary texts of medieval England feature trees as essential to the individual and communal identity as it intersects with nature, and the compelling qualities and organic processes associated with trees help vernacular writers interrogate the changing nature of this character. The early depiction of trees demonstrates an intimacy with nature that wanes after the tenth-century monastic revival, when the representation of trees as living, physical entities shifts toward their portrayal as allegorical vehicles for the Church's didactic use. With the emergence of new social categories in the late Middle Ages, the rhetoric of trees moves beyond what it means to forge a Christian identity to consider the role of a ruler and his subjects, the relationship between humans and nature, and the place of women in society. Taking as its fundamental premise that people in wooded regions develop a deep-rooted connection to trees, this dissertation connects medieval culture and the physical world to consider the variety of ways in which Anglo-Saxon and post-Norman vernacular manuscripts depict trees. A personal identification with trees, a desire for harmony between society and the environment, and a sympathy for the work of trees lead to the narrator's transformation in the Dream of the Rood. …