The Pacific Crest Trail has become increasingly popular since Clinton Clarke first envisioned such a trail in the 1930’s. By comparing the original motives and experience of the trail to the realities of the trail today, the trail’s fluid narrative becomes apparent. While this narrative is ever changing, over the course of the trail’s history one theme has remained constant – a notably problematic relationship with wilderness rooted in an exaltation of the sublime and post-frontier ideals. This thesis focuses on how the Pacific Crest Trail’s development over the past eighty years has created an experience that, on the surface, is notably different from Clarke’s original vision for the trail, but is still influenced by a perception of wilderness born from a romanticization of nature and a pursuit to preserve the western frontier. Chapter one, The Historic Trail, investigates Clarke’s manners and motives behind promoting the trail. Chapter two, The Popular Trail, examines the visual culture surrounding the trail, from nineteenth century landscape painting to the trail’s presence in social media today. Chapter three, The Trail Community, focuses on the growth of a strong community of hikers, and what this means for the future of the trail.