Technical Abstract: On a region-by-region basis, nowhere in the U.S. has the landscape been so completely enlisted into feed grain crop production than the region represented by the Upper Midwest. National maps showing where corn and soybean crops are annually grown demonstrate all the necessary elements are in place to productively and efficiently grow these two crops foundational to the modern human food supply. These elements include highly productive soils, ideal growing seasons with generally sufficient water without supplemental irrigation, well-developed storage and transportation systems that capitalize on major river ways, extensive agribusinesses providing crop inputs and equipment sales and maintenance services, and two centuries of human experience managing the landscape. While production of these feed grains is extremely successful here, the mono-culture, annual crop system has also disrupted important landscape ecosystem functions resulting in major environmental challenges. Federal, state, and local governments continue to spend millions on educational programs and conservation practices addressing these issues and yet many environmental issues persist. Now crop production has a growing demand with biofuels. The same factors found to make the Upper Midwest so productive for feed grain production are also projected to be essential for developing a sustainable biofuel feedstock production system. Thus the question often asked is “Can both food and biofuel production systems coexist? While market pull will ultimately shape how the Upper Midwest landscape is managed in the future, the convergence of food and biofuel production needs creates a unique opportunity to optimize crop production systems. The working hypothesis of this chapter is that by integrating food and biofuel production within the landscape, productivity can be improved over the current monoculture, feed-grain system and will simultaneously promote greater landscape ecosystem services. The guiding principle for accomplishing this will be diversification. Greater diversity is needed with: 1) crop selection (e.g., grain crops, oil crops, herbaceous perennials, woody crops); 2) placement of crops to match soil and landscape resources; 3) crop genetics developed and marketed with landscape performance criteria included; 4) critical inputs necessary in highly productive crop management systems (e.g., use and reuse of nutrients), and 4) delivering and processing of plant products into feed and fuel commodities.