A multi-ethnic, Muslim majority city which is home to Turkish, Pomak, Roma and Bulgarian Orthodox populations of Southern Bulgaria, Kardzhali has been an industrial and mining hub during the communist era. The deindustrialization of the region after the collapse of communism in 1989, together with the entry of Bulgaria into the European Union (EU) in 2007 recast the inhabitants of Kardzhali as the cyclical labor migrants working in Western European industries. This paper focuses on the shifting transportation infrastructure of Kardzhali and the different types of labor mobilities they engender in order to understand their role in the region formation processes of two transnational projects, namely Eastern Bloc communism and the European Union. Through a comparison between the communist era road construction projects which connected the workers of communism to their mining areas and factories, and the EU built “Pan-European Corridors” which are not only the symbols of Bulgaria’s Europeanization but also the material networks between Kardzhali residents and their working sites in Western Europe, this paper reflects on the changing mobility regimes of these transnational projects. By centralizing the precarities of the cyclical migratory workers of Kardzhali, it problematizes the idealized freedom of mobility discourse which is at the heart of the European project. Moreover, throughout the paper, region making is regarded as a contested realm in which competing interests and expectations of multiple parties enter into negotiation. In this sense, the paper also considers Turkish government’s religious and political interventions on this Muslim majority region as another aspect of the current region formation processes.