Abstract: A container watering system and method are provided. A gardening container can include an interior shell and an exterior shell. The interior shell includes an interior base and an interior wall. The exterior shell includes an exterior base and an exterior wall. The interior shell and exterior shell enclose a fill chamber. At least a portion of the fill chamber is between the interior base and the exterior base. The interior shell includes an interior opening that fluidicly couples the fill chamber with a volume partly enclosed by the interior wall. The exterior shell includes an exterior opening. The exterior opening is adjacent to the fill chamber.