Old Oaks Country Club features one of the more rare design / construction collaborations in golf course architecture. Certainly A.W. Tillinghast has many designs in New York, but very few were constructed by C.H. Alison (who, along with Harry Colt, was quite an in-demand team). It was a sensible decision, however, as Alison was already in the neighborhood, having designed Century Country Club, which is right across the highway in White Plains.
Old Oaks is a true out-and-back routing, as only the opening and closing holes take place on the west side of Purchase Street. The other 16 holes are routed within a plot on the east side; despite the relatively landlocked parcel, Rees Jones was able to find an additional 200 yards for the course during 2016, bringing the total distance from the back tees to 6,900 yards.
No. 7 is perhaps the most photographed hole on the course; the par three plays slightly downhill, with a creek that flows down from the tee to the left of the green, where it continues into a larger collection pond. Almost every bit of water on this property is connected to this pool in some way or another.
The current 18 holes are the remnants of 27 original Tillinghast holes on the property; the others were lost to road construction long ago.