Since the sense of time is strongly influenced by advancing age, this laboratory study aimed to find out more about older pedestrians’ decisions to cross the road, focusing on their estimates of how long it would take them to cross. The walking times of older female adults with or without any walking impairment and of healthy young adults were recorded on a walkway representing a road section. Participants also performed actual and imagined crossings of this “road” as well as a duration production task. Results showed that misestimated crossing times were related to the individual time base, with stronger time distortions in some older participants. A comparison between the older participants with disabilities and their age-paired counterparts without disabilities revealed an overestimation of crossing time in the former, affording them a bigger safety margin.