The Whippoorwill Club’s beginnings
can be traced back to the mid-1920s when a group of about 30 successful men purchased the Afterglow Farm from landowner George MacKay. The men secured a 500-acre estate occupying one of the highest points in the towns of New Castle and North Castle and proposed to develop it as a country club colony. 

The group employed Olmstead Brothers, famous landscape architects of Boston, to lay out the property and Donald Ross, a leading golf course architect, to design the course. All 18 holes were to lie on the east side of Whippoorwill Road. The rest of the land was divided up into home sites. 

In 1928 the group members brought in a professional country club developer, Frederick Ruth, for advice and counsel. He had previously been responsible for the Mid-Ocean Club in Bermuda and the Fishers Island Club off the Connecticut shore. Ruth then hired another golf course architect, Charles Banks, to redesign the Whippoorwill course. Banks had worked with Charles Blair Macdonald on the Yale and Mid-Ocean courses and with Seth Raynor on the Fishers Island course. 

Construction began by early 1929 on the new golf holes, new roads and a number of homes. A steam shovel was lost along the way; according to legend it sank out of sight while the pond on the current seventh hole was being built. That loss, coupled   with the extensive ground moving work required to construct Whippoorwill, led to the course architect’s nickname: Charles "Steam Shovel" Banks.  
 

Donald Ross, a leading golf
course architect, was employed to design the course.

Banks built a golf course magnificent in its beauty and design which also presents a great test of golf. He was focused on detail and how the landscape would impact the strategic play of holes. Banks gave Whippoorwill “template” holes: the fourth (Short Hole), the eighth (Biarritz) and the eleventh (Redan). He is credited with the design of more than 30 golf courses and it is said that he believed Whippoorwill to be his masterpiece. 

Despite the financial turmoil in the fall of 1929, the club opened for business the next summer. However the club and golf course suffered during the Depression years and there was little money around for upkeep. After World War II, restoration work began. Local realtor Louis Calder spearheaded the project. Golf holes were brought back to life and, later, a new clubhouse was opened. In 1946 Calder’s real estate company owned the property   and the newly incorporated Whippoorwill Club leased it. A clubhouse was constructed in 1953 

While it was not until 1966 that the club’s membership assumed title of the property, after 1953 there were additions and changes made to the club facilities, including the addition of tennis and platform tennis courts, the pool, and a grill room, and improvements to the golf course, locker room, kitchen, and dining room. But by the turn of the century the original clubhouse needed a major overhaul. As a consequence, the membership approved construction of the current clubhouse which opened in April 2001. Because the pool-house was also in poor shape, a new pool-house opened in 2003.  
 

Charles “Steam Shovel" Banks left it a course that is not only beautiful, but presents a great test of golf.

In May 2014, the club received substantial funds from the New York City Department of Environmental Protection. In return, the club agreed to enter into a conservation easement which restricted development of about 104 of the club’s 172 acre site under which ground water flows into the Kensico Dam. In large part due to this funding, the Club completed a series of capital projects, including renovation of the bunkers and installation of a state-of-the-art irrigation system in 2015; a new turf management facility in 2016; reconstruction of the golf range and construction of a new short game practice/teaching area in 2017; and substantial renovations to the clubhouse including completion of the Bank’s Bar, Ross Grill Room and Calder Dining Room, an expanded patio space and other exterior amenities in 2018. 

Terrific improvements to the Whippoorwill Club have continued over more recent decades and the club’s facilities are among the finest in the area. The golf course has been called a “hidden gem” by the Metropolitan Golf Association and Whippoorwill is also recognized nationally. Since 2003, when it ranked the course 78th, Golfweek magazine has perennially ranked Whippoorwill in the top 100 of “classic” golf courses (built before 1960) in the country. Most recently the Whippoorwill course was ranked 75 by Top 100 Golf Courses of the USA 2018. Whippoorwill truly is one of the nation’s great courses and clubs.
 

In 2000, a new clubhouse, reminiscent of turn-of-the-century New England golf clubs, was sited to afford dramatic views of the course.