Doll Mountain is located within Hancock, Massachusetts. The Taconic ridgeline continues north from Doll Mountain as Smith Mountain, south as Holy Mount and its ridge spur called Mount Lebanon, and to the east as Shaker Mountain. It is bordered by West Hill and The Knob to the west across the Wyomanock Creek valley. The west side of the mountain drains into Wyomanock Creek, then into Kinderhook Creek, thence into the Hudson River and Long Island Sound. The east side drains into Lily Brook, thence to the Housatonic River and Long Island Sound.