Technical Abstract: Achieving sustainable agricultural landscapes in grassland environments is a broad, perhaps audacious goal, yet the need for change is undeniable. Today’s agriculture and food systems are deeply rooted in the era of cheap energy, an assumption of static climate, and the ability of entities to “externalize” environmental and social costs. Disarray in global financial systems has led to more open discussion of rights and responsibilities of individuals and corporations as well as the role of government in economic systems. With growing world population, increased demand on water supplies, increased vulnerability to climate extremes, and low global food stocks, it is time to rethink how to provide secure and resilient food systems and enhanced economic opportunities in rural communities. While the pressures are diverse and great, times of change present opportunities to reassess options and choose new directions. Participants in the Farming with Grass conference, held in Oklahoma City, Oklahoma, from 20-22 October 2008, set out a vision for agriculture based on sound ecological principles with economic accounting for environmental services and costs. Four grand challenges of agriculture–achieving sustainable bioenergy production, adapting to and mitigating global climate change, improving water quality and availability, and ensuring food security–are interrelated and must be addressed systematically, so that today’s solutions do not create tomorrow’s problems. Past policies have favored a few commodity crops, and disfavored producers of grasses and other perennial crops. Perennial species, incorporated into diverse agricultural systems, have great potential to enhance resilience against uncertain climate and market conditions. Additionally, by developing on-farm and rural enterprises, agriculture can help revitalize communities and provide healthy, local food options. A fundamental re-thinking of agricultural policy and practice to maintain or increase production, mitigate past environmental damage, provide healthier foods (particularly to children and the poor), and increase opportunities in rural areas is proposed.