<p>In any urban setting, we come across strangers daily. Despite their fleeting nature, relationalities between urban inhabitants unknown to each other are an essential feature of urban life. Acknowledging such relationalities have previously been argued to have a positive influence on urban inhabitants’ lives, this research aims to gain a deeper understanding into urban inhabitants’ positive interactions with strangers during neighbourhood walks and to explore how subjective meanings attached to such encounters contribute to social cohesion. As a mixture of leisure, utility, and sociability, walking represents a multifaceted physical and social activity. This study used a combination of walking diaries, walking maps, and semi-structured interviews with 45 inhabitants of a mid-sized city in Ontario, Canada. The findings of the qualitative content analysis suggest urban inhabitants’ positive interactions with strangers not only have a positive influence on their wellbeing, but also constitute an important parameter to reinforce their sense of safety and belonging to their neighbourhoods and the community therein, and to their connection to society at large. The multilayered benefits accrued through interactions with strangers in everyday mobilities underscore the importance of fleeting relationships in urban life and are discussed with an emphasis on social cohesion and placemaking.</p>