This data release includes winter cover crop field sampling data (2006-2021) collected from Maryland farms, along with two seasons of Maryland cost-share program field enrollment data (2019-20 and 2020-21) and associated satellite-derived vegetation index values, supporting the remote sensing analysis of winter cover crop environmental performance on fields receiving incentive payments. Files include: 1. CoverCropFieldData.csv - containing springtime field sampling data collected from 2006 to 2021 at the USDA ARS Beltsville Agricultural Research Center, Beltsville, Maryland, and from working farms on the Delmarva Peninsula, Maryland. 2. Maryland_20192020EnrollmentData.csv - containing winter cover crop cost-share program enrollment data (all fields) for the state of Maryland, for the Fall 2019-Spring 2020 season 3. Maryland_20202021EnrollmentData.csv - containing winter cover crop cost-share program enrollment data (all fields) for the state of Maryland, for the Fall 2020-Spring 2021 season 4. Metadata_Remote_Sensing_and_Field_Data.xml - metadata file describing the datasets On-farm data geolocations are privacy protected under a research agreement with the Maryland Department of Agriculture, and are therefore not included in this Data Release. For access to geolocations, please contact the authors.