Remote sensing data are used to map the extent of croplands. They are especially useful in sub-Saharan Africa (SSA) where landscapes are complex and farms are small, i.e. less than two ha. In this study, a hierarchical remote sensing approach was developed to estimate field fractions at 30 m spatial resolution in a highly fragmented agricultural region of Ethiopia. The landscape was stratified into crop production system (CPS) zones with ten-day SPOT Proba-V 1 km normalized difference vegetation index (NDVI) composites. The CPS zones were used to disaggregate agricultural census statistics to 1 km field fractions and mask “wet” and “dry” seasons. Long-term average wet-dry season NDVI and topographic information derived from 30 m Landsat-8 (OLI) surface reflectance and the SRTM digital elevation model were combined with 1 km field fractions in a Generalized Additive Model (GAM) to produce the field fractions. Sample dot grids were manually interpreted from very high-resolution DigitalGlobe imagery on the Google Earth platform for training and testing. The model yielded an Area Under the Curve (AUC) of 0.71 and R2 of 0.65 in the holdout sample set. The high AUC reveals the model was effective at classifying 30 m pixels as “crop” or “not crop” while the high R2 indicated leveraging at the extremes (100 and 0% probability), meaning at 30 m resolution, subpixel variations were difficult to discern. The improved model skill compared to previous cropland mapping studies using GAMs can be attributed to the stratification and decomposition of the Landsat time series using CPS-defined phenology. Additional remote sensing model inputs, such as Sentinel-1 radar backscatter and Sentinel-2 red-edge reflectance, could provide additional explanatory power. Wall-to-wall national coverage for agricultural production estimation or other food security related application could be achieved by manually digitizing additional sample data in other regions of Ethiopia or using existing crowd-sourced databases, such as Geo-Wiki.