The contribution probes the burgeoning phenomenon of city twinning by engaging with four city-pairs transcending and challenging the difference-producing impact of national borders in northern Europe (Imatra–Svetogorsk; Tornio–Haparanda; Valga–Valka; Narva–Ivangorod). It also aims at discussing the dynamics and meaning of twinning in a broader, more principled and critical perspective. Despite a number of obstacles, city twinning has more recently turned into an established form of overcoming of the divisive effects of borders. The model of cities re-imagining their borders, activating them through increased cooperation, not only changes the local landscapes but may entail broader state-related and European consequences as well.