Until recently, local and regional food system development efforts have emphasized small scale direct marketing activities, while food freight transportation policy and planning have primarily focused on distribution infrastructure for large-scale commodity products at the global and national scale. As the demand for local food continues to increase, innovative and scale-appropriate infrastructure and expertise are needed to respond to the market pull. The key question among the stakeholders continues to be: “How can we better move sustainable food products to meet regional market demand?” USDA’s Agricultural Marketing Service (AMS) and the University of Wisconsin-Madison Center for Integrated Agricultural Systems (CIAS) are collaborating to focus on transportation and distribution issues in order to facilitate effective growth in local and regional food systems. In 2013, more than one hundred farmer/shippers, distributors, and wholesale buyers met in LaCrosse, WI to discuss innovations and challenges to moving local food in the Upper Midwest. Researchers, Extension educators, planners and NGOs listened and summarized some of the conversations around communicating value, logistical challenges, and creating more sustainable food supply chains. The process catalyzed a series of discussions and actions within the region. Our current project is investigating strategies that may optimize food freight operations into the Chicago mega-region, with a focus on realizing multi-modal opportunities with freight trucks.