Drawing on the postscript by Cai Jing on the scroll of A Thousand Li of Rivers and Mountains as direct evidence, and the activities of Cai Jing and Emperor Huizong as indirect evidence, supplemented by the physical materials of the imperial silk fabrics Emperor Huizong favored his subjects with, this paper preliminarily investigates Wang Ximeng’s life experience amid the political turmoil of the late-Northern Song Dynasty. His admission to the Imperial Painting Academy, his service in the Imperial Archives, and his learning of painting under Emperor Huizong were all influenced to some extent by Cai Jing’s manipulations and operations. An analysis of the scenes depicted in the Scroll indicates that Wang Ximeng was well acquainted with the natural and cultural landscapes of various regions, including Xianyou in Fujian, Mount Lu and Poyang Lake in Jiangxi, Suzhou, Kaifeng, and other places. Furthermore, under the instruction of Emperor Huizong, Wang Ximeng broadened his vision of panoramic depiction of grand mountains and vast rivers and mastered refined artistic expression of grand blue-and-green landscape painting. He visualized in his painting the poetic sentiment of “Viewing Mount Lu from Pengli Lake” by Meng Haoran, thereby expressing the aesthetic ideology of “Abundance, Prosperity, Joy and Grandeur” that was prevalent in the late-Northern Song Dynasty.