A system includes a timing determination module configured to be disposed onboard an approaching vehicle system during travel of the approaching vehicle system along a first route toward a crossing between the first route and a second route. The timing determination module is configured to determine one or more arrival times of the approaching vehicle system to reach the crossing and to repeatedly communicate notification messages having the one or more arrival times to a remote crossing system that is configured to activate one or more warning devices disposed at or near the crossing to notify other vehicles on the second route that the approaching vehicle system is approaching the crossing along the first route. The timing determination module is configured to determine the one or more arrival times at different respective locations along the first route as the approaching vehicle system travels toward the crossing.