Woody plant encroachment—the conversion of grasslands to woodlands—continues to transform rangelands worldwide, yet its causes and consequences remain poorly understood. Despite this being a coupled human-ecological phenomenon, research to date has tended toward ecological aspects of the issue. In this paper, we provide new insight into the long-term relationships between human demographics and woody plant cover at the landscape scale. We used time-series aerial imagery and historical census data to quantify changes in population, land ownership patterns, and woody cover between 1937 and 2012 in three different settings in central Texas, USA. Woody cover closely paralleled population in a semi-urban watershed (R² = 0.81) and two separate clusters of rural watersheds (R² = 0.88 and 0.93), despite exhibiting very different directional trends over time in each setting. Woody cover also closely tracked average farm size in each rural watershed cluster (R² = 0.57 and 0.90). These results highlight a tight coupling between demographic trends and the extent of woody plant cover. Such human factors may explain a great deal of woody plant cover patterns in other global rangeland systems with similar historical contexts and serve as a predictive proxy of landscape trends. Accordingly, policy recommendations should consider these demographic factors, and future woody plant encroachment research should explicitly include human dimensions.