Processes of land degradation and regeneration display fine scale heterogeneity often intimately linked with land use. Yet, examinations of the relationships between land use and land degradation often lack the resolution necessary to understand how local institutions differentially modulate feedback between individual farmers and the spatially heterogeneous effects of land use on soils. In this paper, we examine an historical example of a transition from agriculture to forest dominated land use (c. 1933–1941) in a highly degraded landscape on the Piedmont of South Carolina. Our landscape-scale approach examines land use and tenure at the level that individuals enact management decisions. We used logistic regression techniques to examine associations between land use, land tenure, topography, and market cost-distance. Our findings suggest that farmer responses to changing market and policy conditions were influenced by topographic characteristics associated with productivity and long-term viability of agricultural land use. Further, although local environmental feedbacks help to explain spatial patterning of land use, property regime and land tenure arrangements also significantly constrained the ability of farmers to adapt to changing socioeconomic and environmental conditions.