Technological changes have opened up new opportunities for historical research, which call for new methodologies to fully realise these opportunities. This paper presents the four-step interactive photo timeline analysis we developed to analyse large volumes of historical photographs from both a quantitative and qualitative perspective. We present the results of a case study (regarding both street design and street use in Vienna from 1860 to 1949) in which we utilised interactive photo timeline analysis. The geographical research scope was limited to the streets around the Vienna Opera: street use and street design were analysed from the perspective of the street as transportation space and as urban living space. The development of the interactive photo timeline analysis methodology and the case study analysis benefited greatly from the interdisciplinary nature of the research team.