Problem, research strategy, and findings As active transport planning gains momentum worldwide, our study underscores the importance of connecting people and places by focusing on the convenience dimension of walkability. Specifically, we used the pedestrian detour ratio (PDR) to measure the degree of circuity of a walking route. We considered residential buildings as origins and 10 different types of public facilities as destinations within the walkable range of 1 km. This led to a territory-wide analysis covering 3.85 million origin–destination pairs in Hong Kong. Overall, walking convenience was the best in the central business district (CBD), but variations existed by district and by facility. Through an assessment matrix, 35.8% of home–destination pairs required attention. When examined at the street block and village cluster levels, walking inconvenience was associated with vehicle-oriented street blocks (with higher vehicular traffic and more private parking spaces), high-income areas, and difficult terrain. Pedestrian crossings, major roads, and bus stops enhanced route directness. This research is a first step in helping quantify the PDR distribution across different cities and their various functional areas. Takeaway for practice In areas where walking is inconvenient, treatments to calm vehicular traffic and facilitate pedestrian crossings should be stipulated. In the longer term, we recommend integrating the PDR in the design and planning of streets, especially around essential facilities.