Pedestrians aged over 65 are known to be a critical group in terms of road safety because they represent the age group with the highest number of fatalities or injured persons in road accidents. It is widely recognized that the latter is due to the physical vulnerability of this age group in case of injury. However, physical and cognitive decline come into play during the action of crossing a street. Various studies have attempted to connect the crossing behaviours of the elderly with variables such as age, gender, sensory acuity, level of attentiveness, physical decline and the design of intersections. In demonstrating the complexity of the relationship between people and their environments, the literature suggests that age, physical ability, and the spatial configuration of roads are major components of road safety. Moreover, people's knowledge and mastery of their environments, as well as their ability to adapt to change affects how they move through space. Taking these factors into account, this study examines the perceptions of elderly pedestrians with regards to the quality and risks of road crossings in the context of Montréal, Québec, in Canada. The analyze are based on observations and questionnaires in order to bring to light a better understanding of the relationship between the crossing behaviours, characteristics and perceptions of the elderly. While previous studies have examined perception and observation separately, this study is unique in having looked at both angles simultaneously. Five profiles of elderly people in both urban and suburban environments were established. A sample of 181 elderly pedestrians (65-93 years of age, AVG = 74) were surveyed using a questionnaire. In addition to close-ended questions, respondents were asked to evaluate 17 environmental ambiance and risk behaviours according to various scales. Using principal component analysis (PCA) and hierarchical cluster analysis (HCA), the data was grouped into 6 categories that define and distinguish 7 profiles of elderly people. These profiles were explored according to the socioeconomic status and crossing behaviours of respondents. The probabilities of adopting different crossing behaviours were tested by employing logistic regression models. The results reveal greater variability in the perceptions of the elderly in terms of risk related to crossing behaviours and type of signalisation at intersections. Even among seniors, the perceptions of risk varied greatly, which may have had an impact on their behaviours. While some of the behaviours observed coincided with the perceptions of respondents, the results of this study suggest that they only play a marginal role.