Understanding the importance of historic land-use legacies has become an integral aspect of natural resource ecology and management in recent years because it adds explanatory power to our current interpretation of ecosystem structure and function; it also reduces the likelihood of missteps in anticipating or managing future conditions. To these ends, the overall goal of my dissertation research was to identify the patterns of landscape and rural community change, and the relationships between them, in three rural Iowa townships between 1930 and 2002. To achieve this goal, three objectives were established (1) to holistically understand agricultural landscapes as linked socio-ecological systems by investigating the strength of linkages between agroecosystem and farm community change over time; (2) to assess the magnitude, rate, and direction of change in land cover for the purposes of understanding how landscape diversity and spatial complexity have changed over time; and (3) to understand the role of U.S. Farm Bill policy as a key driver of land-use and land-cover change over five policy eras. I used historical-comparative research design principles to guide the overall direction of the exploratory, descriptive, and explanatory components of this study. Metrics were derived from aerial photographs, agricultural censuses, and demographic censuses. Overall results showed that fostering the diversification rather than the further homogenization of agricultural landscapes was more likely to achieve the common goal of enhancing rural vitality. More heterogeneous landscapes could be expected to create more opportunities for the next generation of Iowa farmers and foster economic development. My historical-comparative analyses suggests that ways to get there might include reintegrating livestock and crop enterprises to once again capture production synergies; introducing more crops or different cropping systems, consistent with the natural resource limitations of agricultural landscapes, to support existing or emerging markets for food, fiber, and fuel; and assisting rural communities assess infrastructure needs in support of existing or emerging markets for agricultural goods and services. To facilitate these new opportunities, a new approach to U.S. Farm Bill policy is needed. Historically, U.S. Farm Bill policy has employed a "command and control" resource management paradigm intent on isolating and controlling target variables (i.e., income stability on farms, commodity supply management, and soil protection). At the same time, non-target variables (i.e., environmental and social landscape factors) have unintentionally been allowed to slowly change, resulting in the overall erosion of agroecosystem resiliency. Because there is a growing sense that new Farm Bill policy approaches are needed to facilitate the transition to agricultural sustainability, methods that engage broader stakeholder groups and employ multidisciplinary perspectives are more likely to address the once non-target variables that are now visibly important (e.g., environmental degradation and rural community decline). Relinquishing command and control and instead adopting an adaptive management strategy, which acknowledges that human policies are designed to meet social objectives and must be continually modified and be flexible for adaptation to changing conditions, may provide the solution.