The purpose of this study was to explore the mechanism of anticipatory control of gait in relation to the perception of an obstacle. Typically developing (TD) children (4–7 years of age) and children with Down syndrome (5–6 years of age) walked and stepped over obstacles of two different heights—a “subtle” obstacle that was placed at a very low distance from the floor (1% of total body height) and an “obvious” obstacle that was placed at a much higher distance from the floor (15% of total body height). Spatial and temporal measures of the gait cycle were analyzed. TD children showed increased variability in pre-obstacle step lengths only in response to the higher obstacle. Children with DS showed a decrease in variability in response to the higher obstacle and marked qualitative changes in their gait cycle. Both groups of children were able to scale toe clearance with obstacle height. These results show that TD young children can make task-specific anticipatory adjustments by modulating step length and toe clearance. Children with DS show appropriate scaling of toe clearance and are beginning to show the emergence of anticipatory responses under specific environmental conditions.