Across the country, interest is growing in the promise of urban agriculture to support more efficient, sustainable, and equitable ways of life. In Springfield, Massachusetts, through the leadership of the Springfield Food Policy Council and other community-based organizations, projects are underway to promote community-oriented and commercially oriented youth farms, home gardens, orchards, and community gardens. Significant challenges remain, however, to accessible, sustainable, and successful food production in the city. This report examines some of the benefits of and obstacles to urban agriculture in Springfield, and identifies strategies for overcoming the most significant barriers. It uses a GIS-based methodology, developed specifically for the City’s physical and social conditions, to evaluate the suitability of land for community gardens, commercial farms, community farms, and urban orchards, with a particular emphasis on city-owned, structure-free vacant lots. The process is meant to be scalable and applicable to other land suitability assessments. This report offers a model for how landscape designers and planners can work hand-in-hand with communities to develop achievable and sustainable urban agriculture plans.