The risk: reward for a transition to organic vegetable farming near urban areas and changes in soil, crop, and economic parameters during transition are poorly understood. A 4-year study was initiated in 2003 at the Ohio State Univ.–OARDC to document the relative advantages of four transition strategies and their effects on major cropping system variables. Soil previously in a vegetable-agronomic crop rotation has been maintained fallow, planted to a mixed-species hay, used in open field vegetable production, or used in vegetable production under high tunnels, transition strategies with a range of management intensity and expected financial return. Each strategy was replicated four times within the overall experimental area. Half of the soil in each strategy unit was amended with composted dairy manure while the remaining soil was unamended. Field vegetable plots have been planted to potato, butternut squash, and green bean. High tunnels have been planted to potato, zucchini, and a fall–spring rotation of beet, swiss chard, mixed lettuce, radish, and spinach. Data describing the outcomes of the strategies in terms of farm economics, crop yield and quality, weed ecology, plant pest and disease levels, and soil characteristics (physical, chemical, biological) have been recorded. Inputs in the high tunnels have exceeded inputs in all other strategies; however, high tunnel production has widened planting and harvesting windows and increased potato yield, relative to open field production. To date, compost application has increased crop yield 30% to 230% and influenced crop quality, based on analytical and human panelist measures. Weed (emerged seedlings, seedbank) and nematode populations also continue to vary among the transition strategies.