Under what institutional arrangements do entrepreneurship flourishes within particular regions has been and still is a central question in entrepreneurship research. Entrepreneurial regions have been traditionally observed through the lens of ecosystems. This conception, although relevant, overlooks the active ingredients of organizational life, which have profound effect on the mind-sets, feelings and behaviors of individual and collective actors. This paper seeks to tackle this challenge by focusing on a more fine-grained, location-sensitive conceptualization of entrepreneurial regions, which moves the discussion away from ecosystem thinking towards a regional social-geographic understanding of the phenomenon. Our work seeks to explore the complexity underlying entrepreneurial regions and uncover the many “optimal” combination of conditions leading to strong entrepreneurial activity. Based on social geography and institutional complexity, we introduce a location-sensitive framework and test several configurational hypotheses predicting strong entrepreneurial activity. Each configurational hypothesis deals with alternative combinatorial expressions of entrepreneurial regions, understood as combinations of constructed and narrated attributes.