The aim of this study was to systematically investigate the influence of various walking surfaces and footwear characteristics on the ability to terminate gait rapidly in 10 young and 26 older people. Subjects walked at a self-selected speed in eight randomized shoe conditions (standard versus elevated heel, soft sole, hard sole, high-collar, flared sole, bevelled heel and tread sole) on three surfaces: control, irregular and wet. In response to an audible cue, subjects were required to stop as quickly as possible in three out of eight walking trials in each condition. Time to last foot contact, total stopping time, stopping distance, number of steps to stop, step length and step width post-cue and base of support length at total stop were calculated from kinematic data collected using two CODA scanner units. The older subjects took more time and a longer distance to last foot contact and were more frequently classified as using a three or more-steps stopping strategy compared to the young subjects. The wet surface impeded gait termination, as indicated by greater total stopping time and stopping distance. Subjects required more time to terminate gait in the soft sole shoes compared to the standard shoes. In contrast, the high-collar shoes reduced total stopping time on the wet surface. These findings suggest that older adults have more difficulty terminating gait rapidly than their younger counterparts and that footwear is likely to influence whole-body stability during challenging postural tasks on wet surfaces.