The concept of peripherality has recently gained renewed interest in European affairs. Peripheral areas are plagued by issues such as small population size spread over a large geographical area and even depopulation, low rate of innovation and entrepreneurship, as well as high transportation costs and low accessibility. This study on peripheral areas is framed by the EU funded project: Social Entrepreneurship-- Transboundary Strength for Regional and Local Development in Sparsely Populated Environments, whose overarching question is how political entrepreneurship can open possibilities for regional development. Currently this is especially salient as in a Europe of regions, the local competitive advantage is best expressed through the realization of the place’s potential in part through people’s entrepreneurship. Questions that emerge are: what is the relationship of political entrepreneurship and peripheral/border areas? Are there innate territorial characteristics that promote or stifle it? Furthermore, what is the relationship of political entrepreneurship and multi-level governance? Does multi-level governance constitute a state of disequilibrium, and is this a fertile ground for a political entrepreneur? Does political entrepreneurship need to be reconciled with democracy (Bellone and Goerl, 1992) and what are any possible conflicts between entrepreneurship and democracy? Findings are expected to add to the theorizing of entrepreneurship, particularly through the comparison between Europe and North America, with a view to making peripheral communities better.