Occasionally healthy older adults trip over stationary objects even when seen well in advance. These are known as “inadvertent” trips. The purpose of this study was to determine the prevalence of inadvertent trips in older males and older females under conditions of normal vision with good lighting. We also determined their relationship with unobstructed gait measures and other risk factors associated with falls during everyday activities. Forty-one subjects stepped over an obstacle (height set to 25% of leg length) 100 times. The obstacle was contacted by 15 participants (37%) in a total of 29 trials (0.7% of all trials). Of the 29 obstacle contacts, 52% occurred with lead limb. There was no difference in the frequency of contacts between males and females. Slower stride speed, shorter stride length, and increased gait cycle time variability during unobstructed walking were associated with contacts during the obstacle crossing trials (p < 0.041). Inadvertent trips were also associated with the number of prescription medications taken by participants (p = 0.019) and participants’ maximum reported rating-of-fatigue (p = 0.022). Fatigue was an important factor and 36 subjects (88%) reported an increase in their fatigue across trials highlighting the importance of considering fatigue in all obstacle crossing studies using older adults. We conclude that inadvertent trips are not uncommon in older adults and point to useful future areas of research and risk factors that could be targeted by fall intervention programs