Globally, metropolitan areas have prospered economically while rural areas have been left behind. The course focuses on sustainability opportunities and enterprises in these rural landscapes. Emphasis is on the benefits of small-scale organic farm enterprises, typically with diverse production systems, common historically and now resurgent in the farm to table and local food movements as alternatives to industrial agriculture. Although of global relevance, the course focuses on comparisons between New England and Tuscany. In both these regions, ecological and economic sustainability challenges in the rural landscape include producing food and forest products for niche markets, managing watersheds, conserving biodiversity, and other environmental services, such as carbon sequestration, and diversifying income streams with ecotourism and agritourism. Optimizing this mix of functions while minimizing greenhouse gas emissions and other forms of pollution addresses sustainability goals. We discuss readings on models and analysis of sustainable food production systems, including organic, permaculture, and forest farming systems. Assignments, readings, and student team exercises develop skills in evaluating research in innovative farming, and in cost-benefit analysis (CBA), with spreadsheet modeling of annual production integrated with financial analysis of small-scale enterprises.