Walking develops in a dynamic relationship to its socio‐material environment. A historical perspective helps nuance the multiplicity of interrelating factors that influence the practice. This article focuses on walking in Stockholm between 1880 and 1939, a period of great change to the city’s streets and movement within them. Through a detailed coding of 466 photographs, depicting more than 3,000 pedestrians, we examine micro‐scalar elements, such as the use, material, and demographic of the pavement, to allow us to plot developments in the socio‐spatial character of walking over time. The results reveal stable patterns as well as both gradual and rapid change. The intensity of pedestrians remained over time as did the sociality of streets. With increasing automobility, however, pedestrians were increasingly found on pavements rather than roadways. A slightly skewed gender balance also remained across the studied period, though men’s and women’s more specific street use varied substantially. Meanwhile, the presence of children in streets and their independent mobility declined radically. Some of these patterns also varied across different types of streets. These findings are discussed in relation to urban automobility, wider societal trends, and their relevance to walkability studies and present‐day efforts to increase walking.