This article examines the place of the literary lower-middle-class clerk in the English landscape between ca. 1900 and 1940. It draws attention to “clerical literature”—as typified in works by Arnold Bennett, H. G. Wells, and Shan Bullock—and, more specifically, a subgenre that signposts the emergent interest in getting “back to the land.” At the heart of this subgenre of “rambling fiction,” the male clerical protagonist not only engages with the natural landscape on a journey through rural England but also explores notions of masculinity, heritage, and national identity. By focusing on middlebrow works, largely those written by former clerks themselves, this article argues that clerks were pioneers in drawing connections between a re-masculating exposure to the great outdoors—necessary for suburban, domesticated, office workers—and an appreciation of a particular palimpsest of England's history. In doing so, the clerk helped to popularize the continued association of medievalism, the South of England, and the rural “idyll.”