This study presents a comprehensive evaluation of pedestrian gap acceptance behavior at uncontrolled midblock median openings on four-lane urban arterials in Nagpur, India. Field data were collected from two geometrically distinct locations, namely Site 1 and Site 2, to examine the influence of demographic, vehicular, and geometric variables on critical gap estimation. The critical gap was determined using Raff’s graphical method, with results indicating a substantial difference between the sites: 2.66 s at Site 1 and 5.64 s at Site 2. Statistical analyses revealed that age, gender, luggage carriage, group walking behavior, and pedestrian walking speed significantly affected gap acceptance. Pedestrians walking in groups or carrying luggage tended to accept longer gaps, whereas younger individuals and males were more likely to accept shorter gaps, demonstrating greater risk tolerance. Although vehicle type and speed showed observable trends, the differences were not statistically significant. The geometric characteristics of the site had a marked impact on pedestrian decision-making. Site 2’s wider median, shorter crossing distance, and broader footpaths promoted more conservative crossing behavior. The study recommends infrastructure enhancements such as wider medians, pedestrian refuge islands, and pedestrian-activated warning systems. The findings support the integration of behavioral insights into the design of pedestrian facilities to improve safety in complex urban traffic environments.