In Greece during the last decade, in a context of crisis and precarity, artistic practices significantly increased their presence in public space often aiming at engaging the social base and touching upon the inclusion of different communities. Athens became the epicenter of such practices. The main objective of the paper is to explore grassroots arts and culture initiatives’ role in stimulating community-engaging practices in intensively diverse public spaces, thus contributing to transcultural dialogue and urban co-existence. The paper employs two different artistic urban projects, UrbanDig_Omonia and Victoria Square Project on two Athenian squares, Omonia and Victoria, as case studies in order to elaborate on the contribution of artistic interventions and transcultural dialogue in ‘difficult places’. This is realised on two interrelated levels: i) through community-based artistic interventions, that serve as the ‘ice-breaker’ for transcultural dialogue to diverse communities of ‘locals’ and ‘foreigners’; ii) through continuous community engagement practices that serve as evaluation praxis and provide evidence-based reflections that could feed into cultural and social policy making. It further points to the role of artists and cultural managers as mediators among cultures.