Operations that rely on optically-based Normalized Difference Vegetation Index (NDVI) to track crop productivity, are negatively impacted by cloud cover. In this research, parameters from Synthetic Aperture Radar (SAR) imagery were calibrated to NDVI with the targeted outcome to integrate SAR into Canadian crop monitoring services. Data from fully polarimetric RADARSAT-2 and dual-polarization Sentinel-1B imagery were calibrated to Sentinel-2 NDVI. Random Forest Regression (RFR) and Least Squares Boosting (LSBoost) were tested to calibrate SAR to NDVI (SARcal-NDVI) for six crops (corn, canola, soybeans, wheat, oats and barley). RADARSAT-2 provided the best fit with R2 exceeding 0.84 for canola, 0.87 for wheat and 0.90 for corn and soybeans. Correlations were lower for oats (R2 of 0.72–0.77) and barley (R2 of 0.43–0.64) due to a limited number of fields. Although a global model yielded lower correlations (R2 of 0.80), this model would be easier to implement into operations. Total power, the first and second eigenvalues and VH backscatter were important in reducing model error. The SARcal-NDVI and Growing Degree Days were then integrated into a Crop Structure Dynamic Model to produce daily estimates of crop condition, at field scales. The next step is to test if these daily estimates of crop condition can improve crop yield forecasting for the Canadian agriculture sector.