Sustainability has become a popular trend and policy tool for urban interventions in American cities, including the implementation of sustainable urban agriculture projects. In practice, effective urban agriculture projects require long term engagement in community management of land with a deep connection to the specific context and history of a neighborhood, as the case of The Food Project in Boston demonstrates. The strong presence of The Food Project in Boston’s Dudley Street neighborhood today grew out of a larger neighborhood history that involved a series of unlikely but powerful collaborations. Part of this context is the Dudley Street Neighborhood Initiative’s management of a long term local planning process based on the direct needs and aspirations of local residents—leading to the creation of many community managed resources, including sustainable urban agriculture. Overall, the work of The Food Project and the Dudley Street Neighborhood Initiative is a strong example of how sustainable urban agriculture can grow food and community as part of a larger strategy for the long term community management of land.