A windrower has a first dual-path steering mode, causing a left drive wheel and a right drive wheel to concurrently rotate, wherein the rotation of the left drive wheel is in a direction opposite that of the rotation of the right drive wheel and the position of tailwheel casters are not controlled but are permitted unconstrained rotation. The windrower also has a second tailwheel steering mode non-overlapping in operation with the dual-path steering mode, causing the left drive wheel and the right drive wheel to rotate concurrently in only a same direction and the tailwheel casters are steered based in part on tailwheel caster steer position information received from a sensor.