Emerging biofuel markets in the U.S. Corn Belt are leading to increased production of rowcrops and removal of land from conservation programs. This comes at a time when regional research highlights the importance of perennial cover on key areas of the landscape to promote the continued delivery of societal goods and ecosystem services from agricultural lands. The goal of this research is to analyze how the restoration of perennial vegetation interplays with social and ecological contexts at multiple scales to impact the resilience of communities and landscapes in the rural Corn Belt. I addressed this goal through a series of 33 in-depth interviews with farmers and other rural stakeholders living near Stanhope, Iowa and through a participatory scenario development workshop with regional leaders in Iowa agriculture, conservation, and policy. Qualitative analysis of interview and workshop data was integrated with the results of other social and ecological research and interpreted through the lens of resilience theory. I found that farmers and rural residents perceived their "countryside" primarily in social terms, identifying strongly with the farming lifestyle and with networks of people across the landscape. While most interviewees approved of landscape-scale restoration practices on marginal agricultural land, implementation of these practices was not a priority in rural culture and rural people voiced little understanding of, or sense of control over, regional institutions. Interview data indicate that future adoption of conservation practices will be based not simply on immediate profitability, but upon a convergence of contextual factors at three key levels: (1) compatibility with infield farm practices, (2) community-level reinforcement through social networks and norms, and (3) consistent, straightforward policies and institutions. Regional leaders also voiced enthusiasm about the potential for perennial conservation initiatives to achieve multi-objective societal benefits including enhanced biodiversity, soil and water quality, farm profitability, and rural vitality. These leaders suggested that the success of such initiatives will be dependent upon building policy mechanisms that integrate working lands and protected areas and link local creativity and initiative with regional vision, support, and accountability. In all instances, strategic collaboration between diverse partners who operate at different levels in the system will be needed to mediate the macro-level, top-down effects of technology, markets, and policy on farmer land-use decisions.