This paper evaluates the economic and environmental tradeoffs at watershed scale by incorporating both economic and environmental risks in agricultural production. The Target MOTAD model is modified by imposing a probability-constrained objective function to capture the yield uncertainty caused by random allocation of farming systems to soil types and by introducing environmental targets to incorporate environmental risk due to random storm events. This framework is used to determine the tradeoffs frontier between watershed net return and sediment yield and nitrogen concentration in runoff in Goodwater Creek watershed, Missouri. The frontier is significantly affected by environmental risk preference.