Information on the spatial distribution of human disturbance is important for assessing and monitoring land degradation. In the Eastern Mongolian Steppe Ecosystem, one of the major driving factors of human-induced land degradation is the expansion of road networks mainly due to intensifications of oil exploration and exploitation. So far, neither the extents of road networks nor the extent of surrounding grasslands affected by the oil industry are monitored which is generally labor consuming. This causes that no information on the changes in the area which is affected by those disturbance drivers is available. Consequently, the study aim is to provide a cost-effective methodology to classify infrastructure and oil exploitation areas from remotely sensed images using object-based classifications with Random Forest. By combining satellite data with different spatial and spectral resolutions (PlanetScope, RapidEye, and Landsat ETM+), the product delivers data since 2005. For the classification variables, segmentation, spectral characteristics, and indices were extracted from all above mentioned imagery and used as predictors. Results show that overall accuracies of land use maps ranged 73%–93% mainly depending on satellites’ spatial resolution. Since 2005, the area of grassland disturbed by dirt roads and oil exploitation infrastructure increased by 88% with its highest expansion by 47% in the period 2005–2010. Settlements and croplands remained relatively constant throughout the 13 years. Comparison of multiscale classification suggests that, although high spatial resolutions are clearly beneficial, all datasets were useful to delineate linear features such as roads. Consequently, the results of this study provide an effective evaluation for the potential of Random Forest for extracting relatively narrow linear features such as roads from multiscale satellite images and map products that are possible to use for detailed land degradation assessments.