Background: Monitoring terrestrial vegetation cover condition is important to evaluate its current condition and to identify potential vulnerabilities. Due to simplicity and low cost, point intercept method has been widely used in evaluating grassland surface and quantifying cover conditions. Field-based digital photography method is gaining popularity for the purpose of cover estimate, as it can reduce field time and enable additional analysis in the future. However, the caveats and uncertainty among field-based vegetation cover estimation methods is not well known, especially across a wide range of cover conditions. We compared cover estimates from point intercept and digital photography methods with varying sampling intensities (25, 49, and 100 points within an image), across 61 transects in typical steppe, forest steppe, and desert steppe in central Mongolia. We classified three photosynthetic groups of cover important to grassland ecosystem functioning: photosynthetic vegetation, non-photosynthetic vegetation, and bare soil. We also acquired normalized difference vegetation index from satellite image comparison with the field-based cover. Results: Photosynthetic vegetation estimates by point intercept method were correlated with normalized difference vegetation index, with improvement when non-photosynthetic vegetation was combined. For digital photography method, photosynthetic and non-photosynthetic vegetation estimates showed no correlation with normalized difference vegetation index, but combining of both showed moderate and significant correlation, which slightly increased with greater sampling intensity. Conclusions: Results imply that varying greenness is playing an important role in classification accuracy confusion. We suggest adopting measures to reduce observer bias and better distinguishing greenness levels in combination with multispectral indices to improve estimates on dry matter.