Nestled on a dramatically undulating and diverse piece of land, Whippoorwill Club is a standout among Westchester County’s exceptional golf courses. Originally conceived as a nine-hole layout by Donald Ross on the clubhouse side of Whippoorwill Road, the course was expanded by Charles Banks, who added holes 4-9 and 12-14 on the other side of the property. Whippoorwill’s modern design is packed with fascinating features, from deep bunkers to intricate green complexes that rival the best in the region, making it a favorite for those fortunate enough to play it.