This dissertation explores the sacred landscapes known as grotto-heavens (dongtian 洞天) in Song dynasty (960–1279) literary representations. Coined in roughly the fourth century by religious Daoism, the concept of grotto-heavens initially referred to a utopia constituted by a nexus of interconnected caves hidden in the divine mountains. During the Song dynasty, this Daoist space developed into a quintessential symbol that prevailed in all walks of secular Song scholar-officials’ cultural lives. By probing the understudied literati writings and Daoist textual materials that focus on grotto-heaven landscapes, this study discusses the overlooked spatial understanding and bodily implications of sacred mountains. It argues that the Song literati used their literary devices to reframe the once forbidden and illusory grotto-heavens as accessible places in actual landscapes. The reified grotto-heaven landscape also reshaped the literati aesthetic of ideal space: it not only became an enchanted vessel for literati to cache Daoism-related memories and explore the knowledge of antiquity, but also catalyzed their intellectual and physical cultivation with nature, the traces of sage kings, and eventually the transcendental order.The main body of this dissertation is divided into four chapters. Chapter One provides a general survey of the origin of the grotto-heaven concept in the Daoist tradition and its reception in literature before the Song dynasty. The overview shows that grotto-heavens were perceived as forbidden and illusory spaces in secular literature before the tenth century. Chapter Two concentrates on the case of Grand Cleanse (Dadi 大滌) Grotto-heaven and demonstrates its transformation from an inaccessible space into a visitable place in the secular Song literati’s literary representations. Chapter Three looks into the incentives that drove Confucian literati to depict the Daoist realm as an accessible place. Although still evoking traditional tropes, the literati visitors absorbed the Daoist teaching of physical cultivation and made their bodies an important factor when writing about their wandering in the sacred mountains. Chapter Four builds on the notion of corporeal landscape and elaborates on how the Song literati represented their self-cultivation of inner alchemy in the grotto-heaven landscape to embody the sage king Yu.