In this article, we discuss issues concerning the development of detailed passability maps, which are used in the crisis management process and for military purposes. The paper presents the authorial methodology of the automatic generation of these maps with the use of high-resolution digital elevation models (DEMs) acquired from airborne laser scanning (light detection and ranging (LIDAR)) and photogrammetric data obtained from unmanned aerial vehicle (UAV) measurements. The aim of the article is to conduct a detailed comparison of these models in the context of their usage in passability map development. The proposed algorithm of map generation was tested comprehensively in terms of the source of the used spatial data, the resolution, and the types of vehicles moving in terrain. Tests were conducted on areas with a diversified landform, with typical forms of relief that hinder vehicle movement (bluffs and streams). Due to the huge amount of data to be processed, the comprehensive analysis of the possibilities of using DEMs in different configurations of pixel size was executed. This allowed for decreasing the resolution of the model while maintaining the appropriate accuracy properties of the resulting passability map. The obtained results showed insignificant disparities between both sources of used DEMs and demonstrated that using the model with the 2.5 m pixel size did not significantly degrade the accuracy of the passability maps, which has a huge impact on their generation time.