The objective of this research paper is to analyze and determine the relationships between childhood and adulthood transit behavior. The study investigates gender differences for each generation regarding childhood transit experiences. Childhood travel socialization was studied to understand its effects on childhood transit experience and perception. Lastly, childhood transit experience and perception were analyzed to determine their effect on adult transit usage. The variables the study analyzed were childhood peer impression of public transit, parental opinion of the safety of public transit, and the respondents’ childhood public transit experience. These variables were investigated to determine if they had an effect on adult use of public transit. The survey Transit Center’s Who’s On Board: 2014 Mobility Attitudes Survey (WOBMAS) was used to perform these analyses. The results showed that gender equality appears to be increasing in younger generations with respect to their ability to travel alone on public transit. In addition, men were more likely to travel by themselves on public transit when compared to women. There is a direct correlation between childhood travel socialization and childhood transit experience and opinion. However, there appears to be no correlation between childhood travel socialization and a child’s likeliness to travel on public transit alone. Childhood travel socialization had a counterintuitive effect on adult transit usage. On the contrary, it appears that childhood experience is significantly linked to adult transit usage. The data suggests that the earlier a person travels on public transit alone, the more likely they are to ride it as an adult.