In this paper, the needs, attitudes, and perceptions of older (50+) cyclists were examined with the aim of determining the level of comfort, safety, and the way of using different types of cycling infrastructure. Considering that by 2050, 1 in 6 people will be over the age of 65, and that this category of users (particularly cyclists) still receives insufficient attention, the authors believed that in this way, a significant contribution can be made to the existing literature. Data from 389 50+ cyclists were collected through a survey, including Canada, the United States (USA), and Serbia, and analyzed using visual preference testing (VPT), ANOVA, and Kruskal–Wallis test. The countries were chosen to include certain similarities (traffic characteristics), as well as differences (cultural characteristics), in order to enable an adequate exchange of knowledge, good practice, and experience. The results indicate the existence of differences between these countries, especially regarding the perception of safety and the way of using certain infrastructure in Serbia (e.g., major urban collectors and shared space). Based on the obtained results, a set of general guidelines was proposed for countries with similar traffic and cultural characteristics on how to treat and provide sustainable infrastructure for older cyclists.