This paper provides an economic analysis that compares the profitability and land management capability of four different organic cropping systems used to produce winter squash (Cucurbita pepo cv. ‘Delicata’) and cabbage (Brassica oleracea var. capitata cv.’ Farao’). The organic cropping systems are part of a long term experiment designed for vegetable production in the Northeast, and designed to maintain ecological integrity and contribute to environmental stewardship. Our research addresses the causal chain from soil processes to economic outcomes including soil quality, efficiency in cycling of nutrients, off-farm impacts, pressures from weeds, insects and diseases, crop yield and quality, and marketing opportunities. Interactive crop budgets were developed to document both production costs and income streams for each cropping system. Using data from the 2009 trial, a ridge-tillage system that relied on cover crops for nitrogen (System 4) yielded the highest revenues for squash production. The results also indicated that System 1, which relies on compost for nitrogen, occasional cover crops and uses conventional tillage, had the highest revenues for cabbage. Subsequent sensitivity analyses were performed across a range of key parameters, and the results indicated that System 1 and System 4 consistently yielded the highest revenues for cabbage and squash production respectively.