The history of Oconaluftee Valley in western North Carolina is a tale of adaptation to sweeping changes in its communities, politics and governance, economic structures, and landscapes. The Eastern Band of the Cherokee found ways to survive profound losses and change brought by colonialism, removal, the Civil War, and waves of manipulation and abuse by the US government, the state, and squatters. The mountain farm families faced their own existential challenges when, from the end of the nineteenth century to the 1940s, large-scale logging and the movement to establish a national park twice transformed the valley. The most successful mountain families found ways to accommodate logging companies and opportunistically participate in the boom without losing ownership of their land. A number of owners leased land—even tracts immediately adjacent to their homes—to logging companies and mills. They worked as loggers, millers, store managers, and clerks, but they continued their subsistence lifestyles. These families viewed their land with both utility and stewardship. When the Great Smoky Mountains National Park was created, similarly, those who adapted more than they resisted were able to stay the longest though eventually all had to leave. This paper will focus on how the people residing in a remote but nationally economically connected valley responded to powerful external challenges. It will seek lessons from their decisions and speculate on how Appalachian communities today can recall the struggles and perseverance while undertaking contemporary efforts to map pathways to resilient, sustainable twenty-first century lives.