DEVELOP's Chesapeake Bay Agriculture project was featured by NASA's Earth Observatory. The primary goals of this project were to automate key steps in acquiring yearly satellite imagery and compute vegetation metrics to assess winter cover crop performance in the Chesapeake Bay. As a test case, four Maryland counties were used to calculate NDVI derived biomass, nitrogen content, and percent nitrogen by field from 2006-2016. In addition, software was developed to calculate the same metrics in future years. Monitoring cover crop performance in the Chesapeake Bay using Earth observations (EO) allows the MD Department of Agriculture (MDA) to confirm cover crop implementation and to inform adaptive management.