The growth rate of adults older than 65 in Canada is increasing more rapidly than the population as a whole. This increase is reflective of the aging baby boomer population. That population is known to have a strong attachment to automobiles, which might be reflected in their travel behavior as they move toward different stages in their older life. The purpose of this paper is to contribute to the understanding of the travel behavior, mainly public transit usage, of Canada’s older population relative to younger cohorts. A pseudocohort analysis was conducted in Montreal, Quebec, Canada, of residents who were 50 or older to follow changes in public transit use of similarly aged respondents from 1998 to 2013. The results revealed that older generations used public transit more than younger generations did at the same age. In addition, the most recent survey year showed a stagnation of transit use across all age groups. Differences in transit use between males and females were more pronounced in earlier cohorts, but the difference was decreasing in more recent years. These findings add to the growing body of work suggesting that the nature of transportation behavior in seniors is changing, and accordingly planners and engineers cannot expect the baby boomer generation to behave the same way as previous generations. Addressing the transportation needs of seniors around the world will be an important challenge for planners and engineers, as the population of seniors is growing more rapidly than the population as a whole in the majority of developed countries. This growth imposes new challenges on the transportation system because of differences in the travel behavior of today’s older adults compared with that of previous cohorts of seniors.