© 2019 Hogrefe Verlag. The study and explanation of regional personality differences is a central research topic in geographical psychology. Such research on regional "mentalities" can inform, for example, studies examining socioeconomic trajectories of regions and local populations. Whereas existing regional personality research mostly concentrated on regions in the United States and the United Kingdom, the present study delivers results for 97 German regions (Raumordnungsregionen). We analyze and aggregate individual-level data collected in the The Big Five Project study (N = 73,756). We compare regional differences in the Big Five traits between urban versus rural regions, East versus West Germany, and Northern versus Southern Germany. The results indicate that: (a) popular stereotypes (e. g., reserved Northerners, jovial Southerners, and open urbanites) may contain a kernel of truth; (b) systematic migration patterns could drive/maintain regional personality differences; and (c) there is a relatively clear CologneMunich line in the regional variation of neuroticism in Germany. Despite the small effect sizes, the present results have new implications for research and practice concerned with the socioeconomic trajectories of German regions.