This dissertation uncovers the contemporary impressions of Song cities represented in Song narratives and their accounts of the interplay between people and urban environments. It links these narratives to urban and societal changes in Hangzhou 杭州 (Lin’an 臨安) during the Song dynasty, cross-referencing both literary creations and historical accounts through a close reading of the surviving corpus of Song narratives, in order to shed light on the cultural landscape and social milieu of Hangzhou. By identifying, reconstructing, and interpreting urban changes throughout the “pre-modernization” transition as well as their embodiments in the narratives, the dissertation links changes to the physical world with the development of Song narratives. In revealing the emerging connection between historical and literary spaces, the dissertation concludes that the transitions of Song cities and urban culture drove these narrative writings during the Song dynasty. Meanwhile, the ideologies and urban culture reflected in these accounts could only have emerged alongside the appearance of a consumption society in Hangzhou. Aiming to expand our understanding of the literary value of Song narratives, the dissertation therefore also considers historical references and concurrent writings in other genres. By elucidating the social, spatial, and historical meanings embedded in a variety of Song narrative accounts, this study details how the Song literary narrative corpus interprets the urban landscapes of the period’s capital city through the private experiences of Song authors. Using a transdisciplinary methodology, it situates the texts within the cultural milieu of Song society and further reveals the connections of these narratives to the transformative process of urbanization in Song society.