There is 1 golf course in Greencastle, Pennsylvania and 0 are municipal courses. There are also another 15 golf courses within 20 miles of Greencastle, including 9 public, 3 municipal and 3 private courses. The oldest course in the Greencastle area is the Monterey Country Club opened in 1903. The longest course is Penn National Golf Club & Inn, which is 7,009 yards. Whitetail Resort is rated the best course near Greencastle. The following courses have won various awards: Penn National Golf Club & Inn.