Trademarks are useful territorial marketing policies contributing to the economic growth of a certain region. However, the complexity of these strategies from a marketing and legal perspective requires a deeper understanding of the functioning of trademarks. We investigate these dynamics for the trademark “Prodotti di Qualità” (PQ), a territorial marketing initiative of Apulia Region (Italy) aiming at enhancing agri-food products with regulated high-quality standards, raising awareness among consumers and promoting marketing and sales of such products. We adopt a multidisciplinary approach to conduct a prospective analysis of marketing issues and a perspective analysis on legal issues. We conclude that, in face of some benefits for users in terms of reduced asymmetric information between consumers and producers, a stronger communication and promotion campaign would increase consumers’ awareness and producers’ confidence, also contributing to avoid the overlap of the PQ trademarks with other legal forms of labelling, such as geographical indications and certification trademarks. Policy interventions in this direction would be beneficial for the future development of the Apulian territorial marketing.