Technical Abstract: To meet Chesapeake Bay Total Maximum Daily Load requirements for agricultural pollution, conservation districts and farmers are tasked with implementing best management practices (BMPs) that reduce farm losses of nutrients and sediment. The importance of the agricultural industry to the regional economy highlights the need for determining cost-effective BMP solutions tailored to geographical and operational characteristics of these farms. This study evaluated both the environmental risk and farm profitability of common farm-level management practices for three major farm types in the region: crop, tractor-based (“English”) dairy, and horse-drawn (“Amish”) dairy. Whole-farm simulations were conducted with the Integrated Farm System Model, a multi-year, process-based simulation model, to facilitate a broader understanding of the challenges for the farmers in finding financially feasible and environmentally sustainable solutions. Strip cropping, conservation tillage, cover cropping, and nutrient management BMPs generally reduced nutrient and sediments losses from all three farm types. However, scenarios that reduced phosphorus and sediment losses generally promoted more leaching of nitrogen. Double cropping corn with winter wheat combined with improved nutrient management was the most profitable practice for the crop farm, increasing average farm profitability by 92% over the baseline condition, while reducing combined nitrogen and total phosphorus losses by 13% and 23%, respectively. Net profitability of the dairy farm was increased only by decreasing manure storage or using improved nutrient management. For the horse-drawn dairy, cover-cropping and harvest of rye silage combined with increased nutrient management provided the greatest increase in farm profit (+8%) and also reduced phosphorus and nitrogen losses.