Saddleback Mountain in Piscataquis County, Maine, lies within the Pleasant River watershed, which ultimately feeds the Penobscot River and Penobscot Bay. Its slopes drain in multiple directions across the surrounding landscape. Water from the northeast end flows from Crater Pond into South Inlet Brook and then to the East Branch of the Pleasant River, while the eastern side drains by Mud Gauntlet Brook into Ebeemee Lake. The southeast side feeds the Middle Branch of the Pleasant River, the southwest end runs through Saddleback Brook into Silver Lake and the West Branch, and the northwest side reaches Silver Lake by Big White Brook.