A bearing cooling system for a vibratory pile driving system comprising at least one housing wall defining at least one bearing opening and at least one bearing assembly supported by the at least one housing wall in the at least one bearing opening. The bearing cooling system comprises a bearing cover plate, a bearing cover seal member, and at least one bearing bolt. The bearing cover plate defines an inner surface having a bearing cover plate seal recess. The bearing cover seal member adapted to be received at least partly within the bearing cover plate seal recess. The at least one bearing bolt is configured to secure the bearing cover plate relative to the at least one housing wall to form at least one contact location at which the bearing cover plate is in contact with at least a portion of the at least one bearing assembly.