Abstract: The correlation between river system, transportation network and the development and evolution of urban settlements is an important point to the study of regional system resilience. The Beijing-Hangzhou Grand Canal has played the role of North-South transportation artery in history, which has driven and affected the development of cities along the canal. Based on the analysis of historical literature and the use of geographic information spatial analysis tools, this research explores the spatial distribution characteristics, evolution process, coupling relationship and interaction mechanism of urban settlements along the canal and water and land transportation network in different periods since the middle and late Qing Dynasty. With the change of regional natural environment and administrative division, and the construction and development of modern high-speed transportation network, the evolution process between the Grand Canal and the transportation network and urban settlements along the Canal presents a dynamic relationship of bilateral selection and coordinated development. According to the relationship, the settlements along the canal can be divided into five types: mutual-promotion, self-superiority, traffic-driven, canal-dependent and new-traffic. In the process of evolution, resilience has become the core element of the smooth optimization and transformation of the cities along the canal, integrating into the new regional development system and reshaping the new life.