The paper explores the correlation between the concepts of territoriality and social practices in the context of urban and rural (re-)production of space. It traces the degree of “habitualisation” of certain actions and the behaviour of stakeholders, identifying those defined as practices, and revealing their role in the (dis-)continuation of territoriality of a region. It takes a German region Ostwestfalen-Lippe (OWL) as a case study. The research methodology is based on the practice theory of Andreas Reckwitz and his “praxeological quadrat of cultural analysis”, which is applied in this study. The research process includes (a) semi-structured interviews with the representatives of several institutions from the region, (b) narrative analysis and thematic content structuring of the interviews and (c) synthesis analysis. The study clarifies relations between the artefacts and discourses mentioned by the interviewees, and their impact on the practices of the institutions and others contributing to the (dis-)continuation of territoriality and identity of the region. The main findings are related to the (1) methodological contribution—operationalisation of the “praxeological quadrat of cultural analysis”, and (2) substantive contribution—revealing the role of social practices on the continuation of territoriality of the region. The article presents cultural patterns in the perception of and orientation towards long-past territorialities by the interviewees and makes clear what significance these historical and historicising spatial references have for the spatial planning of the present