Cross-border territories face complex and multi-scalar challenges, among which the management of cross-border transport is of crucial importance, both in terms of international competitiveness and everyday mobility planning. In this paper, the study of transport as a key element of regional development in the cross-border context of Regio Insubrica (the region straddling the border between Italy and Switzerland, comprising the Canton of Ticino, the Lombardy provinces of Como, Lecco and Varese and the Piedmontese provinces of Novara and Verbano-Cusio-Ossola) was approached from the perspective of infrastructure, specific local potentials and stakeholder strategies. Focusing on cross-border cooperation aspects, this research seeks to identify trends and dynamics that may hinder or promote the development of an integrated and competitive cross-border area interconnected by an efficient transport system.