North of Jiminy Peak , the valley of Kinderhook Creek cuts through the hills. Here the westernmost ridgeline is dominated by Misery Mountain and Berlin Mountain and extending into Pownal, Vermont; the easternmost, which terminates in Williamstown, Massachusetts is ruled by Mount Greylock , the highest point in Massachusetts. Between these is the long ridge of Brodie Mountain. The area hosts three long distance trails (the Appalachian Trail, the Taconic Crest Trail, and the Taconic Skyline Trail) and an extensive network of smaller trails.