This paper conceptualizes trade fairs as complex socio-spatial phenomena, which are constantly transformed, following socio-economic change, and reflect aspects of social and urban life. Methodologically, we apply a longitudinal systematic comparative analysis of historical fair evolution between international practice and the case of the city of Thessaloniki, exploring convergence and divergence, throughout the historical evolution of the city. It is shown that Thessaloniki fair exhibits similarities and differences vis-à-vis the international practice, with these linking to the socio-economic conditions of the city. Fair activity in Thessaloniki exhibits a time lag in integration of international practices while incorporating economic, social, cultural, and political dimensions. Particularly within the conditions of the 2008 global economic crisis, Thessaloniki fair emerges as a hybrid model that combines fairs’ strategies and social and urban practices with aspects of pre-modern, modern, and post-modern fair forms, significantly influenced by the historical evolution of the urban context.