The purpose of the current study was to use the margins of stability (MoS) to investigate how older adults choose between minimizing the risk of a forward fall when crossing an obstacle and the ease of maintaining forward progression during the steps taken behind the obstacle. In the current study 143 community-dwelling older adults aged between 55 and 83 years old, were divided into three age groups based on tertials of age. All participants were asked to complete five trials of obstacle walking and five trials of normal walking. For the trials of normal walking, the main difference between groups was that MoS at initial contact was lower in the older age groups. For the trials of obstacle crossing the MoS at the instants of obstacle crossing with both the leading and trailing limb became smaller with an increase in age. This result might imply that older people choose to use a strategy during obstacle crossing that results in smaller chance of falling forward if an obstacle was struck. A negative consequence of this more conservative strategy was a smaller MoS at the instants of initial contact after crossing the obstacle, thus a larger chance of a backward fall. These findings provide more insight into the regulation of stability during obstacle crossing and specifically in the differences in strategy between younger and older people, and therefore these results might be used for further research to investigate whether obstacle crossing strategies are trainable in older adults, which could be used as advisory programs aimed at fall prevention and/or engagement in an active lifestyle.