The intersection of homelessness and transportation is an overlooked component of transport-related exclusion research, yet mobility is recognized as playing a significant role in anyone’s well-being. The lack of research in this field is concurrent with the lack of understanding of homeless individuals’ mobility needs and travel behavior. As a result, there is little that can guide the policy-making process for the travel needs of homeless individuals. In 2015, as a response to this research gap, an interview was designed and then conducted with 159 homeless individuals across eight shelters and drop-in agencies in the city of Toronto, Canada. The interview included stated adaptation experiments to reveal how transportation affected or hindered homeless individuals’ activity participation processes. Decision choice models were estimated with econometric modeling methods, which indicated the influence of variables such as age, income, and duration of homelessness on the decision to reject or accept employment opportunities. The results also showed that a person’s accustomed mode choice and daily number of trips had an effect on the decision to travel for social activity purposes.