Afterglow Farm was the Mackay family's name for their 500-acre estate occupying one of the highest points in the towns of New Castle and North Castle, Westchester County.  It was sold in the mid-twenties to a group of some thirty men who proposed to develop it as a country club colony.

The property lay on both sides of Whippoorwill Road at the northern end of what is now the golf course.  The cobble-stone and clapboard main house, since burned down, stood directly back of the present tenth tee.  The cobblestone building just to the west, now used for the storage of equipment, was called the "Cabins," and here each of the Mackay sons had his own quarters.  In the center of the building was a chapel with an adjoining room for a resident priest.        

A clubhouse of fifty bedrooms (each with private bath), on the property's highest point would cost $275,000, including furniture, equipment and proper treatment of the grounds.  The budget included $150,000 for roads, $40,000 for landscaping by Olmstead Brothers, $5,000 for mosquito control and $1,500 for livestock, presumably riding horses.

The group who bought the Mackay farm added some adjoining property and started to develop it.  They incorporated as the Whippoorwill Country Club, Inc. employed Olmstead Brothers, the famous landscape architects of Boston, to lay it out and Donald Ross, a leading golf course architect, to design the course.  All eighteen holes lay entirely on the east side of Whippoorwill Road.  The rest of the property was divided up into the home sites.

Successful men though the group of members were, they presently realized that their talents ran along other lines than country club development, and in 1928 they called in a professional for advice and counsel.

This professional was Mr. Frederick S. Ruth, who had made a somewhat conspicuous success in the development of three club colonies - the Mid-Ocean Club in Bermuda, the Mountain Lake Club in Florida and the Fishers Island Club on Fishers Island, off the Connecticut shore.

Now, Fred Ruth was a man of sweeping imagination and vast self-confidence, perfectly geared to the lush era in which he operated.  His proposal to the group was this: expand the property to 850 acres and thereupon launch the promotion of "a fine, dignified, proprietary club colony" on the deluxe scale to which he was accustomed.  As he wrote at the time, he envisaged "a thoroughly high-toned development," made up of people "all imbued with the desire for greater privacy and social protection than is now afforded by any other club within commuting distance of New York, to be owned by that portion of the discriminating public which appreciates the distinctive and the beautiful and which would like to spend its summers in a really private park, among only the most delightful surroundings, and with every facility for enjoying the best of the out-of-doors."

The founding group was intrigued by Ruth's proposal and embraced it.  Another famous golf architect, Charles H. Banks, completely redesigned the course.  Banks had recently designed many other courses in the area, including Tamarack, Hackensack (N.J.), Knoll Golf Club (N.J.) and Castle Harbour.  He also worked with Charles Blair MacDonald on the Yale and Mid-Ocean courses and with Seth Reynor on the Fishers Island course.  The rationale behind bringing Banks in to rebuild the course is unknown. However, all we need to know is that Banks left a truly remarkable golf course that is not only beautiful, but presents a great test of golf. 

Charles Banks was not a formally schooled golf architect, but neither were many of his contemporaries.  Most of those not trained were simply good players who used an innate sense of the game to create strategic interest within the site’s natural constraints. Today,   Whippoorwill is considered to be one of the best of the courses based on the C.B. Macdonald/Raynor/Banks philosophy which incorporated highly regarded design traits that stemmed from the best early courses in Europe. These European courses were characterized by frequent use of geometric and often extreme course features. 

Unlike some of the golf architects of his era, Banks was keenly focused on detail. He understood how even the smallest of details would impact the way the course set on the landscape and how such details would impact the strategic play of the course. As one of Banks’ first courses independent from the direction of Seth Raynor, Whippoorwill’s course includes features that are even bolder than those for which Raynor became famous. Many of these were likely the result of the extreme topography of the Whippoorwill site. 

For example, the 11th hole is Whippoorwill’s Redan hole. The “Redan” is usually a par 3 on which the green is wider than it is deep, and angles diagonally away from the tee box. That is, the left side of the green is farther away from the tee box than the right side of the green. A Redan hole slopes right-to-left, and is often guarded by a deep bunker confronting the middle part of the green, or bunkers on the right and left fronts. The tee shot may play slightly uphill to a green surface that is partially or fully blind to the golfer.

All of the Redan holes are modeled after the original Redan at North Berwick Golf Links in Scotland.  North Berwick's Redan made its debut in 1869. It has remained essentially unchanged since. Redan holes earn their reputations as "fortresses" by presenting a challenging test to the golfer. It's often an extremely tough shot to keep the ball on the putting surface of a Redan hole.

The 4th hole is an example of what would be called the "Short Hole" within the repertoire of Seth Raynor and Charles Banks.  Intimidation is an important ingredient in this type of hole, with the bunkers surrounding the green looking like an island in a sea of sand.              

In 2000 the new 20,000 square foot clubhouse was sited in the same location as the original clubhouse in order to afford dramatic views of the golf course.  The new clubhouse was designed in the classic shingle style, with a wood shingle roof, wood siding, and painted wood trim that is reminiscent of turn of the century New England golf clubs.  The new landscaping included the transplanting of several mature trees from various areas around the golf course.  Construction was completed in April, 2001.  

All of the improvements to the course and our facilities over the past few years have led to a better appreciation of Whippoorwill by the golf world. For years, Whippoorwill has been recognized by the Metropolitan Golf Association as the “hidden gem” of the area golf courses.  Whippoorwill is also recognized nationally. Golfweek magazine and other publications perennially rank Whippoorwill in the top 100 of “classic” golf courses (built before 1960) in the country.