Whippoorwill at Whippoorwill Club

Whippoorwill Club sits in Armonk, New York, approximately 40 miles north of Manhattan in Westchester County. Donald Ross designed the course in the mid-1920s, during the prolific period when he shaped many of the region's most enduring layouts. The property occupies rolling, wooded terrain typical of northern Westchester, with elevation changes that Ross incorporated into his routing to create natural strategic interest and varied shot values throughout the round.

The course reflects Ross's characteristic design principles: greens with subtle interior contours and false fronts that reward precise approach play, bunkers positioned to influence tee shot strategy, and holes that use the land's natural movement rather than impose dramatic artificial features. The routing moves through mature hardwood forests and over ridgelines, with several holes playing across or along the property's elevation shifts. Ross's green complexes demand careful club selection and thoughtful short game execution, as many putting surfaces tilt or feature sections that reject poorly flighted shots.

Whippoorwill operates as a private club with a membership drawn largely from Westchester County and nearby Fairfield County, Connecticut. The club maintains a traditional atmosphere focused on golf and family recreation. Over nearly a century, the course has remained relatively intact to Ross's original design intent, though typical maintenance and tree management practices have evolved with the times. The layout provides a study in Ross's ability to create strategic golf on terrain that offers natural variety without requiring extensive earthmoving.