A ladder stabilization and lighting system comprising a ladder stabilizing boot, comprising a base pad and a plurality of vertical walls extending upwardly from the base pad, where the plurality of vertical walls extending upward from the base pad form a rectangular recess configured to provide a friction fit on a ladder rail end, and where the base pad is configured to be a flat planar surface larger in area than the ladder rail end. The ladder stabilizing boot further comprises a light positioned on at least one outer surface of the plurality of vertical walls, where the light is powered by a power source in electrical connection with the light and a switch.