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A Thousand Miles of Streams and Mountains (Qianli jiangshan tu 千里江山圖) is the name of a famous 12-meter-long landscape painting of the Northern Song dynasty. It was painted in 1113 by a 17-year-old prodigy, Wang Ximeng 王希孟, under Emperor Huizong’s 徽宗 (r. 1101–1125) supervision, an accomplished painter and a Daoist initiate himself. In this paper I argue that the handscroll depicts a story of Daoist self-cultivation, from lay-life, initiation, receiving training, to eventually attaining Dao (becoming immortal) and the afterlife as an immortal. This story is depicted in both the iconographic details of the figures, buildings, paths, bridges and other elements, guiding the viewer through the landscape, and the composition of the handscroll, mirroring the development of the story by means of the particular placement and the form of the landscape. Because of his close involvement, the landscape painting offers a unique and amazing insight into Huizong’s personal views on what constitutes a Daoist and Daoist self-cultivation, if not his ideas on Daoist landscape painting in the Song dynasty.