This article explores the practice and triumph of unconventional gender expression that were central concerns of Abby Williams Hill's writing from the American West, particularly from 1902 to 1906. Hill, a professional landscape painter, created romantic representations of the wilderness to fuel the popular fantasies of American frontier life. This essay turns to her unpublished journals and letters to argue that Hill pursued a contradictory project in her daily life and personal writing, documenting the work of resisting social expectation from within an idealized space. Hill understood that one does not escape the overlapping ideologies of gender, sexuality, race, and social class in the West, yet the voluminous diary entries and letters that she produced during her travels reveal that she also recognized the natural world as a site in which cultural formations might be more malleable and thus more open to revision. This article contends that Hill claimed for herself and her children the transformative potential of that exclusionary space. More so than her western landscape paintings, Hill's personal writing models an alternative mode of engagement with the natural world as a space to critique and revise the status quo.