Transhumance, the oldest form of animal management, has been practiced since the Neolithic era, involving animal domestication and adaptation to regional environments. The mountainous Iberian Peninsula, with its hot, dry summers, naturally favored transhumance, widely adopted in Spain and Portugal. In Portugal, records of long-distance transhumance date back to prehistoric times, peaking in the medieval period and continuing into the late 20th century. This activity was vital for centuries, especially in Portugal’s mountainous regions reliant on grazing, with evidence of movement from the North (Gerês to Trás-os-Montes), Center (Montejunto to Estrela), and South (Monchique, Espinhaço de Cão, and Caldeirão) involving sheep, goats, cows, and pigs. Today, only a few locations still practice a transtermitance type of migration along ancient Estrela routes, underscoring the need to support these vanishing communities. The last recorded long-distance route taken by transhumant shepherds was to Serra de Montemuro in 1999. Currently, folklore and tourism provide a glimpse into the historical practice of transhumance in these regions. The future of Portuguese transhumance remnants relies heavily on tourism, sporadic academic initiatives funded by European projects, and financial support from municipalities that recognize the benefits of integrating traditional systems into modern land management models. Rethinking current and future perspectives highlights the necessity for resilient integrated models to revive these practices.