Since the 1990s, important regeneration processes have been carried out around urban waterfronts and canals. Urban waterways have undergone a transformation from industrial canals and navigation corridors towards focal points for revitalization and urban development. But, what new roles and values do the canals have as part of sustainable cities development? This article discusses the illustrative case of Regent’s Canal, London. The aim is to reveal the relationship and perception changes around Regent’s Canal environments through an evolution of its cityscape. Using historic evidence, policy documents, and fieldwork, the article identifies practices of regeneration of the canal’s banks in a reciprocal relationship between its capacity for place-making and the influence of the city on its transformation. Although Regent’s Canal constitutes a single, continuous element, it defines a changing and more diverse linear canalscape, as a result of the layering of various uses and values like an historical transport, environmental, scenic, and recreational corridor.