Obstacle crossing, such as stepping over a curb, becomes more challenging with natural aging and could lead to obstacle-related trips and falls. To reduce fall-risk, obstacle training programs using physical obstacles have been developed, but come with space and human resource constraints. These barriers could be removed by using a virtual obstacle crossing training program, but only if the learned gait characteristics transfer to a real environment. We examined whether virtual environment obstacle crossing behavior is transferred to crossing real environment obstacles. Forty participants (n = 20 younger adults and n = 20 older adults) completed two sessions of virtual environment obstacle crossing, which was preceded and followed by one session of real environment obstacle crossing. Participants learned to cross the virtual obstacle more safely and that change in behavior was transferred to the real environment via increased foot clearance and alterations in foot placement before and after the real environment obstacle. Further, while both age groups showed transfer to the real environment task, they differed on the limb in which their transfer effects applied. This suggests it is plausible to use virtual reality training to enhance gait characteristics in the context of obstacle avoidance, potentially leading to a novel way to reduce fall-risk.