A system and method for generating a trip plan for a vehicle system determine a first trip plan for a trip of a vehicle system from a first location to a second location over a first route that includes a first intersection with a second route. The first trip plan designates operational settings of the vehicle system. An alternate trip plan that extends along the second route from the first intersection to the second location of the trip of the vehicle system also is determined. The first and alternate trip plans are determined prior to the vehicle system reaching the first intersection. Movement of the vehicle system is controlled according to the first trip plan prior to the vehicle system reaching the first intersection and then controlled according to the alternate trip plan responsive to the vehicle system deviating from the first trip plan.