In this article, the authors assumed that the “iGeneration” is the leading driving force for the SMART orientation of modern cities. Dynamic and multidirectional technical and technological processes introduce a new level of changes in urban space, adapting it to the present and future requirements of its inhabitants in a sustainable manner. An important infrastructure element of the urban space is the crosswalk, being an inseparable element of everyday life in the city. As part of a clear emphasis on the issue of vulnerable road users’ protection, the aim of the article is to examine the perception of users regarding crosswalks in Poland, based on the example of Szczecin. The main aim of the article is to identify the dimensions of crosswalk perception. The specific objectives include the determination of the state of knowledge about the essence and typology of crosswalks and the identification of good practices in their designation. Literature analysis, questionnaire research, and a case study were used. In the adopted research methodology, the use of the questionnaire made it possible to identify key intersections (Five Stars), each different in their form, and to learn about the perception dimensions of this element of urban space. In the context of the Smart City concept implementation, the perception of crosswalks by young city residents, i.e., the “iGeneration”, was examined. The obtained results allowed to perform a systematic analysis that focuses on individual behavioral aspects and subjectivism of the assessment of crosswalks in comparison with the commonly dominant architectural, engineering, and legal perspectives. The research allowed to assess the topology of intersections as well as the indication of safety improvement recommendation lists, taking into account intergenerational optics.