Throughout history, rivers and lakes have wielded a profound influence on the dynamics of urban transportation expansion. To illustrate this phenomenon, we turn to the century-long evolution of the road network in Wuhan, China, as a case study. The study aims to explore the relationship framework between water bodies and urban transportation, characterized by the sequence of “strong connection” to “weakened connection”, then to “mutual restriction”, and ultimately to “mutual benefit”. Additionally, the analysis of the impact mechanisms of rivers and lakes on urban transportation at different stages of development is also a key research objective. To facilitate our exploration, we select the road networks in Wuhan from four years of 1922, 1969, 1995, and 2023 as the primary research subjects. By establishing water buffers, we scrutinize the evolving characteristics of riverside and lakeside transportation amidst the city’s expansion. Based on the modified shortest path model, we introduce the innovative concepts of “Detour Index” and “Weighted Detour Index” to assess the road accessibility of each node in the city based on its inherent environmental conditions. This allows for the effective analysis of the potential impact of water bodies as “obstacles” on the road network at different stages of urban development. The study found that in the areas adjacent to the rivers and lakes in Wuhan, there is insufficient road accessibility based on their inherent environmental conditions. Particularly, some areas along the rivers may become “terminals” in the urban road network. Furthermore, during the process of urban expansion, the correlation between the urban road network and rivers continues to weaken, while the correlation with lakes continues to strengthen. These conclusions can provide valuable insights for the planning of urban roads near water bodies.