A vehicle control system and method includes identifying a segment of a route where one or more first vehicle systems were operated manually instead of operated by one or more processors according to one or more trip plans during prior traversals of the segment by the one or more first vehicle systems. A segment plan is generated for traversing the segment under control of the one or more processors. The segment plan is generated based on how the one or more first vehicle systems were manually operated during the prior traversals of the segment. One or more second vehicle systems are controlled with the one or more processors to traverse the segment according to the segment plan.