Various kinds of garden spaces had been the most important outdoor venue for public entertainment in late-nineteenth and early twentieth-century Shanghai, as they featured a mixture of landscaping, architecture, and leisure activities that originated from different regions in China and cultures of other countries. These garden sites that delineated the ever-changing boundaries of Shanghai evolved closely with this city’s urbanization process. This dissertation rethinks Shanghai gardens, not just as a reflection of modern Chinese landscape architecture in transformation or an embodiment of social and political changes, but as a spatial construction that actively interacted with the changing cityscapes and facilitated new visual experiences and representations. The dissertation focuses on the overlaps between the political and the commercial and the elite and the popular in transforming Shanghai gardens from secluded architectural forms to the city’s open spaces for entertainment and leisure, including the commercial pleasure gardens, temple-gardens, city parks, and rooftop gardens as high-rise building’s playgrounds. These garden spaces are examined along two lines of inquiry. One line focuses on the construction of garden spaces from the architectural and cultural perspectives. I compare those garden architectures of significance to the city’s physical and social development at several key moments from the 1850s through the 1930s. The other line probes into the interplay between the spatial practices and visual culture in the city’s multi-cultural contexts. I search for multiple ways that the production and reception of different visual forms intersected with garden spaces in Shanghai. The study consists of four chapters targeting in sequence the three subjects above: the city, garden spaces, and the interplay between spatial practices and visual culture. By examining an array of city maps, the first chapter investigates Shanghai’s early geopolitical transformation and garden spaces’ close relation to the city’s physical expansion. The second chapter focuses on the material construction of garden spaces and examines how hybrid architectural and cultural features were adapted to and took form in Shanghai during the late imperial and early Republic transition. The third chapter deals with the interlinked garden sceneries and various forms of visual entertainment in night gardens, and the last chapter explores the construction of city parks in relation to the ongoing urban planning advocated by the Nationalist government and mass-produced printed images during the early twentieth century. Taken together, this dissertation elaborates the dynamic intersection of the city’s urban expansion, garden spaces, and visual culture over the critical century in modern Chinese history.