Older drivers, who are the fastest growing segment of the U.S. population, experience high crash rates. An analysis was performed to evaluate potential problem maneuvers that may lead to higher crash involvement. Left turns against oncoming traffic, gap acceptance for crossing non-limited-access highways, and high-speed lane changes on limited-access highways are identified as such maneuvers. Older and younger driver accident propensities are measured, using Kentucky crash data. The findings of the analysis show that older drivers are more likely to be involved in crashes related with these maneuvers compared with younger drivers; older male drivers are safer than older female drivers in left-turn crashes and gap acceptance-related crashes, and having a passenger beside the older drivers makes for a safer driving environment. Potential countermeasures aiming to reduce the accident rates of older drivers are discussed.