Organic producers in the mid-Atlantic region of the USA are interested in reducing tillage, labor and time requirements for grain production. Cover crop-based, organic rotational no-till grain production is one approach to accomplish these goals. This approach is becoming more viable with advancements in a system for planting crops into cover crop residue flattened by a roller–crimper. However, inability to consistently control weeds, particularly perennial weeds, is a major constraint. Cover crop biomass can be increased by manipulating seeding rate, timing of planting and fertility to achieve levels (>8000 kg ha−1) necessary for suppressing summer annual weeds. However, while cover crops are multi-functional tools, when enhancing performance for a given function there are trade-off with other functions. While cover crop management is required for optimal system performance, integration into a crop rotation becomes a critical challenge to the overall success of the production system. Further, high levels of cover crop biomass can constrain crop establishment by reducing optimal seed placement, creating suitable habitat for seed- and seedling-feeding herbivores, and impeding placement of supplemental fertilizers. Multi-institutional and -disciplinary teams have been working in the mid-Atlantic region to address system constraints and management trade-off challenges. Here, we report on past and current research on cover crop-based organic rotational no-till grain production conducted in the mid-Atlantic region.