Dairy production is a key agricultural enterprise in the Upper Chesapeake Bay (UCB) basin, where phosphorous (P) and nitrogen (N) loading contribute to eutrophication. Import of forages and grains and application of mineral fertilizers contribute to nutrient imbalances in the basin. The UCB Long-Term Agroecosystem Research Cropland Common Experiment aims to evaluate diverse crop rotations that minimize the need for imported feed, maximize year-round living cover, and reduce nutrient losses. UCB's plot-scale experiment was established in 2018, incorporating an ongoing cropping system study that was established by the Pennsylvania State University in 2010. An alternative dairy cropping rotation (including silage and grain corn [Zea mayes L.], alfalfa [Medicago sativa L.]/orchardgrass [Dactylis glomerata L.] mix, winter rye silage [Secale cereale L.], and sorghum-sudangrass [Sorghum × drummondii (Steud.) Millsp. & Chas]) that employed manure injection, integrated pest management, and less frequent manure application was compared to a prevailing, conventionally managed silage corn-alfalfa rotation with higher manure application rates. A field-scale experiment was established in 2019 to monitor alternative production practices (manure injection and avoidance of neonicotinoid seed treatment) and prevailing practices in three fields on a commercial dairy farm. Findings suggest that crop rotation diversification, manure injection, and integrated pest management have the potential to increase the economic and environmental sustainability of dairy cropping systems, but long-term evaluation is needed for confirmation.