Under the mining condition of extrathick coal seam, the overburden moves violently, the surface is destroyed seriously, and the discontinuous deformation such as cracks is fully developed. Taking Datong mining area as an example, this paper studies and analyzes the development characteristics and generation mechanism of surface cracks in loose layer covered area and bedrock exposed area by means of field measurement and similar model experiment. In the bedrock exposed area, there is no main crack. The width, length, number, and step drop of surface cracks are relatively small. There are many cracks with the same scale and distributed evenly and parallel. However, in the loose covered area, the main cracks are mainly located above the open-off cut and the stoppage line side that is deviated from the working face. There are many secondary cracks around the main crack, with a large crack density and a few cracks in the outer edge of the main crack. Through research, it is found that three mining faces belong to the typical three-zone mining mode and the main fracture is consistent with the O-ring fracture distribution theory. This research’s results can provide theoretical and technical support for the follow-up land remediation and ecological restoration.