Railway trespassing is a very risky but common behaviour, resulting in about 200 casualties annually in the Czech Republic. This study describes the formation of 27 selected risk localities with frequent occurrence of trespassing in the regions of southern, central and northern Moravia. To be able to describe the process, an evaluation of the development of land use was conducted within a wide spatial context of each spot. The evaluation was focused on functional use of built-up areas (collective and individual housing, industrial areas, shopping and services, recreational areas, etc.). In the sample of investigated localities were places of two kinds: (1) localities where the railway intersected existing settlement structures, and relationships and links within the area were radically disturbed and severed. A lack of legal possibilities for crossing restricts the movement of inhabitants at these localities; (2) localities where the railway originally passed through open landscape and was later surrounded by built-up areas with various land-use functions. Here, trespassing is the consequence of gaps in the urban-planning process, wherein the needs of pedestrians and cyclists were not sufficiently considered. The analysis of the development of land use since 1836 showed how the motivations of trespassing were gradually intensified with more and more complex structures of functional division of areas. The percentage of built-up areas increased in all monitored localities overall from 6.28% during 1836-1852 to 52.15% during 2014-2015.