Winter cover crops encompass a range of species planted in late summer and fall for a variety of reasons relating to soil health, nutrient retention, soil compaction, biotic diversity, and erosion prevention. As agricultural intensification continues, the practice of winter cover cropping remains a crucial practice to reduce leaching from agricultural fields. Maryland and Delaware both incentivize cover cropping to meet water quality objectives in the Chesapeake Bay Watershed. These large-scale programs necessitate methods to evaluate cover crop performance over the landscape. Cover crop quantity and quality was measured at 2,700 locations between 2006-2021 with a focus on fields planted to four cereal species: wheat, rye, barley, and triticale. Samples were GPS located and timed with satellite remote sensing observations from SPOT 4, SPOT 5, Landsat 5, Landsat 7, Landsat 8, or Sentinel-2. When paired imagery at 10-30 m spatial resolution , there is a strong relationship between the normalized difference vegetation index (NDVI) and percent ground cover (R2=0.72) as well as NDVI and biomass (as high as R2=0.77). There is also a strong relationship between Δ Red Edge (a combination of 740 nm and 783 nm bands) and nitrogen content (R2=0.75). These equations were applied to Harmonized Landsat Sentinel-2 products and used to estimate cover crop aboveground biomass in ~300,000 ha of Maryland Department of Agricultures and ~60,000 ha of Delaware Association of Conservation Districts enrolled fields from 2019-2021 and grouped by agronomic method. Wintertime and springtime cover crop biomass varied based on planting date, planting method, species, termination date, and termination method. Early planted fields had higher wintertime biomass while fields that delayed termination had higher springtime biomass. Triticale had consistently higher biomass while wheat had the lowest biomass. Fields planted using a drill followed by light tillage or no-till drill had higher biomass, likely due to the better seed-to-soil contact. Fields that were taken to harvest or terminated for on farm use (roller crimped, green chopped) also had higher springtime biomass than other termination methods. Incentives can be used to encourage specific agronomic methods and these findings can be used to inform adaptive management in the Mid-Atlantic Region.