Examining the images of West Lake from the thirteenth to the nineteenth century in China, this dissertation focuses on the representation of the place as a topographic, historic, and cultural site. Following two lines of inquiry, this dissertation explores the boundaries and efficacies of site-specific paintings while probing the long-perceived Song (960–1279) lineage of West Lake paintings. This dissertation considers paintings of West Lake as images constructed from vision, experience, memory, and history. These images participated in the promotion of local identity in the Ming dynasty (1358–1644) and the forging of an imperial landscape during the Qing (1644–1912). This dissertation comprises an introduction, five chapters grouped into three parts, a conclusion, a coda, and two appendices. Chapter 1 identifies three key visual formats in the representation of West Lake: the bird’s-eye panoramic, the close-up scenic, and the linearized panoptic. Each format considers a different way of experiencing West Lake: the desire to overlook the lake from a high vantage point, the impulse to personally explore the seasonal and temporal changes on the lake, and the need to tour the lake in a boat. Chapter 2 demonstrates two spaciotemporalities in the representation of West Lake during the Ming dynasty: the past and the present. Embodying modernity and nostalgia at the same time, West Lake was represented as the lingering ghost of the Song capital city and the display window of the Ming metropolis. Chapter 3 reconstructs the formation of a Song lineage of West Lake paintings during the Yuan (1271–1368) and Ming periods. Parsing visual and textual materials from the tenth century, this chapter provides a comprehensive analysis of the process of rooting the subject matter in the Southern Song (1127–1279) court, while investigating the reasons behind such historical and cultural construction. Chapter 4 explores the imperial footprints on the landscape of West Lake in the Qing era, in situ and on paper. This chapter considers court-commissioned images of West Lake as devices for imperial surveillance and stages for political spectacles. Chapter 5 traces the circulation of West Lake images between Beijing and Jiangnan since the eighteenth century to understand the production, consumption, and perception of politicized images of West Lake. By demonstrating the close relationship between the mass/imperial tours and site-specific paintings, this dissertation considers landscape paintings as agents that confine and regulate viewers’ experiences with the site. By reconstructing the process of consolidating a Song lineage of West Lake images, this dissertation focuses on the making of (art) history through image building and art-history writing. It challenges the traditional wisdom in the study of Chinese painting that the Song court actively participated in the depiction of West Lake. In doing so, this dissertation positions paintings of West Lake in the context of the identity building of the Ming, the forming of multiethnic landscape of the High Qing era, and the secularization of political images after the eighteenth century.