Tompkins County, New York and the larger Finger Lakes region in which it is embedded is the site of a local food systems movement that appears to have originated in and around the city of Ithaca, some 30 years ago or more. As the movement ripens today the accelerated activity reveals that key ingredients of its success are the connections that have been forged over the years between producers and consumers, farmers and ecosystem service providers, families-schools-hospitals and farms; researchers and practitioners and many others. The vibrant local food system of the area appears to provide a foundation for the emergence of a deliberately conceived ecoagricuture landscape that has the capacity to deliver a well balanced blend of agricultural production, environmental conservation and livelihood security benefits to residents of the region. A key question facing food system analysts and planners is, how can we know if and when the local food system is contributing to ecoagriculture landscape outcomes, and how can landscape measurement activity be designed to help advance the system? Furthermore, how can community-engaged assessment activity help actors in the system analyze the conditions under which a local food system is better than ‘the alternative’ and also identify who benefits.