Over the last 10 years, several authors have produced reviews of regional settlement system studies in archaeology (Galaty 2005, Kantner 2008, Kowalewski 2008, Peterson and Drennan 2012, Feinman 2015). They all point out the major methodological and theoretical advances made in the last two decades. Many regional datasets were created and completed, allowing for quantitative and spatial analysis of settlement patterns from a landscape perspective. They also outline the importance of cross-comparison to investigate large-scale patterns, and to contribute to questions of long-term social, environmental, economical and political change. However, the challenge remains to apply a global, comparative approach to regional settings, especially when comparing across national borders. In particular, there is a tension between two contrary perspectives: understanding human experience and contingency on the one hand, and studying trends and similarities in settlement system trajectories on the other. The first one relies mostly on simulation modelling and complexity theory, while the second one is more based on ´traditional´ quantitative methods and spatial analysis, promoting analytical simplicity. To understand regional trajectories within a multiscalar context, however, both approaches appear fundamental. In this round-table we want to evaluate and discuss current approaches to comparative inter-regional analysis in various European countries. How can we exploit existing datasets, stemming from different scientific and heritage management traditions, for cross-border studies? How to develop common procedures for diachronic analysis, applicable to both large-scale questions and regional settings? How to build a bridge between different theoretical and conceptual frameworks?