Transhumance is a practice of nomadic pastoralism that was once common in Mediterranean Europe. This livestock-rearing system is associated with the maintenance of cultural landscapes and the delivery of a wide range of ecosystem services. Although transhumance is still practised in Spain on a small scale, its future is highly uncertain because of socioeconomic constraints and other drivers of change. A participatory scenario-planning exercise with 68 participants, including shepherds, decision-makers, veterinarians, environmental experts, intermediaries from the wool and meat markets, and researchers, was used to envision plausible futures for transhumance and to enlighten policy-making for the maintenance of this practice along the Conquense Drove Road, one of the largest foot-based transhumant social-ecological networks still in use in Spain. Specifically, the aims were to: (1) analyse the drivers influencing the future of transhumance, (2) depict the current situation of transhumance, (3) envision future scenarios for this activity, (4) analyse ecosystem services’ trade-offs between different scenarios and their effect on human wellbeing, and (5) provide some insights for policy-making related to the maintenance of transhumance. Four plausible future scenarios were built, each showing clear trade-offs in the delivery of 19 ecosystem services, such as food, fibre, ecological connectivity, soil fertility, air quality, fire prevention, cultural identity, local ecological knowledge and cultural exchanges, as well as the different dimensions of human wellbeing. As a result of the participatory process, nine management strategies were identified for the maintenance of transhumance. Priority was given to the implementation of payment schemes for ecosystem services, the enhancement of social capital among transhumants and institutional coordination, the improvement of product marketing, and the restoration and conservation of drove roads. Finally, the implications of the current reform of the Common Agricultural Policy in the European Union for the maintenance of transhumance are discussed.