In 2010 Golfweek magazine ranked the Whippoorwill golf course as the 73rd best classic course in the United States.
The course was designed by world-famous golf course architect Donald Ross and renovated by Charles H. Banks.
The course was originally designed by Ross to lie all on one side of Whippoorwill Road, colloquially known as "Squirrel Alley."
Legend has it, among members, that during the construction of the 7th hole a steam shovel sank in the muddy bottom of the pond below the tee box.
On the left side of the 18th fairway, as players are approaching the green and the current clubhouse, the foundation of a monastery.