The objective of this experimental study is to identify the differentiation made by pedestrians, in their crossing decision, between various urban environments, notably in terms of perception of walking pleasantness and safety. This experiment further aims to identify the environmental features that pedestrians use and the inferences they develop to explain their road crossing decision. Sets of five photographs presenting five different environments (city center, inner suburbs, public housing in the outskirts, commercial zone in the outskirts and countryside) have been presented to 77 participants shared in three age groups (pre-adolescents, young and middle adults). Their decision to cross or not, their perception of pleasantness and safety, and the elements they take into account to take a decision were collected for each environment presented. The results show the pedestrians’ perceptions of the pleasantness and safety of public spaces, in terms of walking, largely vary with urban environments. Moreover, the crossing decision significantly varies according to the environment. Pedestrians were significantly more inclined to take the decision to cross in city center than in the other sites presented. The presence and function of the buildings and quality of the sidewalks are key factors to explain their crossing decision, by enabling them to infer the density of pedestrians and traffic and vehicle speed.