For Montréal in the nineteenth century, as for most port cities, the waterfront served as the primary interface between the city and the markets of the world. This paper examines how and why the primitive waterfront of Montréal as of 1830 was repeatedly adapted and transformed into a modern port district by 1914. Beyond a detailed examination of the set of physical changes on the waterfront, this paper draws theoretical insights from geographical interpretations of the rhythm of capital accumulation to explore the formative and adaptive processes underlying waterfront redevelopment. Global innovations in transport and cargo-handling technology are recognised as the preconditions for the periodic redimensioning of the port of Montréal, and it is established that these changes were driven by the perennial demands of local investors to accelerate circulation and thus reduce the turnover time of capital. This paper offers a new perspective on waterfront development by conceptualising the entire port as a comprehensive circulatory system and then exploring the redevelopment of various components in relation to others. The findings indicate that massive increases in traffic—the number and size of ships—through the port were correlated with the redimensioning of all of the connected components of the circulatory system; that is, the major arteries such as the St Lawrence River ship channel, as well as the smaller capillaries like finger piers.