Throughout Chinese history, the Grand Canal served as a regional infrastructure in facilitating socio-economic and political development. The core regions of each dynasty were located in China’s eastern plain, and the Grand Canal ran from south to north through the plain, connecting northern and southern China. In unison, the areas along the Grand Canal also suffered from frequent wars. The role of the Grand Canal in influencing regional stability has yet to be sufficiently explored in the literature. This study seeks to (1) figure out the spatial distribution of population and wars, and (2) quantitatively measure the relationship between wars, population, and the distance from waterways in the Grand Canal Area in AD752–1910 by using their high-resolution geo-referenced data. Kernel density analysis was employed to serve the first purpose, while Pearson correlation and curve estimation analyses were applied to serve the second. Our results show that the areas surrounding the Grand Canal were densely populated. There was a war hot zone in the Beijing–Luoyang–Nanjing region near the Grand Canal, which shifted gradually over time. The correlation between war and population densities was positive, whereas the correlation between war density and distance from the waterway was negative. Finally, the cubic model captures the non-linear relationship between population, wars, and waterways. The above findings may shed more light on the Grand Canal’s role in influencing regional population and war patterns in historical China, a topic that has received little academic attention. More importantly, they may help advance empirical understanding of the impact of large-scale infrastructure on regional sustainability.