Crop residue left after harvest plays an important role in controlling against soil erosion and in increasing soil organic matter content of agricultural soils. Crop residue management is a practice of great importance in southwestern Ontario, where soil management practices have an effect on Great Lakes water quality. The use of remote sensing data to measure and monitor crop residue can be fast and efficient. However, remote sensing–based studies need calibration and validation using field observations. The objective of this study was to determine the optimal number of ground-truthing field measurements (i.e., digital photographs) required to estimate residue levels. To do so, we compared the residue estimates derived from digital photographs with those derived from the standard line-transect method. Residue was measured from 18 fields located in southern Ontario, and data collected included percentage of crop residue using line-transect and photographic grid methods. Results were analyzed using linear regression, correlation tests, ANOVA, and means tests. Analyses were also conducted to retrospectively determine the minimum number of line transects or digital photos required to estimate crop residue cover at specified levels of power. Results showed that (1) percentage of crop residue estimates derived from using digital photographs were strongly correlated (<i>r</i> = 0.91, <i>p</i> < 0.001, <i>R</i><sup>2</sup> = 0.83, and <i>n</i> = 90) to those derived from using line transects; (2) counting 50 to 100 points per digital photograph was sufficient to accurately estimate the percentage of residue cover; and (3) there was greater variability in the results for soybean (<i>Glycine max</i> [L.] Merr.) than for corn (<i>Zea mays</i> L.), with the highest variability for medium-level soybean residue. Overall, the digital photograph method to estimate percentage of residue was found to be a suitable alternative to the line-transect method, which is more time consuming and labor intensive. Determining the optimal numbers of measurements to estimate crop residue cover is important to those wishing to use digital photo capture methods to record, archive, and measure residue for remote sensing calibration and validation or for handheld mobile device applications.