Visual characteristics of terrain affect the properties of pigeon trajectories in medium-distance flights. Pigeon flight often provides a solution to the task of searching for food (foraging), returning home (homing), or exploring territory (surveying). In this work, we considered the flights of single pigeons and pigeon flocks, calculated flight characteristics such as direction, altitude and its deviations, and analyzed reactions to the boundaries between different areas. Based on remote sensing datasets, we identified visual characteristics of terrain, such as the density of surface fill and its distribution over the study terrain, boundaries of single objects, and boundaries between homogeneous areas. Applying spatial analysis, we compared the characteristics of pigeon GPS tracks and features of object distributions on terrain over which birds fly. Our analysis revealed which flight parameters are stable and which, on the contrary, are very sensitive to visually perceived terrain characteristics. We found that the properties of flight over an urbanized area often differ from the properties of flight over a natural landscape. Spatial data—pigeon GPS track records and open-access remote sensing datasets—were processed using the geographical information system QGIS. Our results show that adaptive visual perception can help solve navigation tasks when pigeons fly over mixed terrain. Knowledge of the characteristic features of bird flights can be used both for a better understanding of the spatial behavior of living creatures (humans and animals) and for optimization of artificial intelligence algorithms.