Catamount Ski Area on Mount Fray in the Taconic Mountains spans Hillsdale, New York, and South Egremont, Massachusetts, and remains one of the southern Berkshires’ three ski areas as well as one of New England’s few family-owned resorts. Its origins date to 1937 or 1938, when John “Jack” Falconer Fisher acquired the mountain and began cutting trails; the resort opened in 1939 with three rope tows. Over time it expanded with lifts, snowmaking, racing facilities, and new ownership. Since 2018, major upgrades have continued while the area has grown into a four-season destination with extensive skiing, youth racing, an aerial adventure park, and the Catamonster zipline.