This thesis presents an interdisciplinary cultural history of the Anglo-Saxon relationship with trees and woodland. Although the paramount importance of woodland to the Anglo-Saxon world is a known and undisputed aspect of early medieval studies, the intricacies of the relationship between the Anglo-Saxons and trees have never been fully appreciated because this subject has not, until now, been the focus of an interdisciplinary study. By exploring the representation of trees and woodland in Old English literary culture in the context of Anglo-Saxon literary-historical sources and the early medieval archaeological record, this thesis seeks to shed new light upon the terms of this complex interaction. I present arguments for the existence of a common Germanic tree creation myth, reaffirm the notion of an Anglo-Saxon world tree analogous to the Norse Yggdrasill that was subsequently replaced by the cross, and re-evaluate the role of trees in Anglo-Saxon heathenism and Christianity. I demonstrate that the paramount importance of woodland in Anglo-Saxon material culture was understood, appreciated, and is well represented in Old English literature. Furthermore, I show that attitudes towards the physical make-up of settlements were strongly defined by an enduring attachment to woodland that had its origins in the forests of first-century Germany.