A trailer stand includes a wheel assembly and a carriage. The wheel assembly includes a bearing, a wheel rotatable in connection with the bearing to be rotatable in a first direction, but not rotatable in a second transverse direction, a pivot connectable to the object, and a frame connected to the pivot to be pivotable with respect to the object, the frame sized and dimensioned to support the bearing at an offset with respect to the pivot axis of the pivot to thereby form caster trail, the frame having a mass distributed unequally upon left and right sides of the wheel assembly, thereby causing the frame to pivot with respect to the Earth, to a predetermined orientation, when the frame is tilted with respect to a normal orientation with respect to the Earth. The carriage supports the wheel assembly, and is pivotable with respect to the trailer.