An anchor removing machine is capable of automatically removing anchors from a rail and of windrowing the removed anchors between rails. The machine preferably employs a ram assembly to detach the tail of the anchor from the rail, a field side kicker assembly to drive the anchor towards the gauge side of the rail in order to facilitate anchor removal, and a windrow assembly to engage the head of the anchor and to pull the anchor away from the gauge side of the rail for subsequent pick up. Lateral and vertical alignment between the anchor removing machine and the anchor is assured by opposed plates and by stops, respectively. Preferably, pressure switches or the like prevent the operation of each component in the system until operation of the preceding component is completed.