This paper presents an investigation to assess the risks of road accidents due to visual field occlusions. The experimental arena considered ground-mounted traffic signs and various occluding agents, such as larger vehicles and median/roadside plants. Repeated field trials at horizontal curves and straight sections revealed that city buses/commercial vehicles in urban streets cause significant occlusions, resulting in a considerable deficit between the available and required legibility distances. The current investigation noted that such a deficit often exceeds 50% at curves, even if occluded vehicles move at operating speeds. However, the values are primarily on the lower sides of straight sections due to brevity in target signs and lesser occlusion in the visual field. Roadside plants often create vegetation shades, further exacerbating visual field occlusion. The study, thus, indicates the need for future research to comprehensively investigate such visual field occlusions, particularly on roads with mixed-mode traffic.