UPDATE 9/16/26: Mystery Friday Foto #37 Solved: A Flight Over Clarence Mackay’s Harbor Hill Estate
UPDATE 9/16/26- Frank Femenias has updated his Google Maps overlay of the Harbor Hill Estate
Click HERE to see Franks's overlay.
Did you identify this plane, estate and Motor Parkway connection?
Identify;
- The Plane
A Fairchild FC-2 with The Roosevelt Flying Corporation livery painted on the side. The Roosevelt Flying Corp was one of several aviation companies operating out of Roosevelt Field in the late 1920s, providing short-haul air transport, charter flights, and aerial excursions. Flights like this were common, particularly over recognizable North Shore landmarks, and were often used for demonstration, promotion, or photography.
- The estate and it's two buildings shown. Who owned the estate?
Clarence Mackay's Harbor Hill Estate's mansion in the lower portion of the photo. Carriage house and horse stables seen further up.
- The approximate year
This photo from 1929 was from a postcard of the same year.
- Link any element of the photo to the Motor Parkway
Owner of Harbor Hill was Clarence Mackay. He was an original director/incorporator of the Long Island Motor Parkway.
Congrats to Joseph Oesterle, Steve Lucas, Scott Engbarth and Frank Femenias for identifying Harbor Hill. Kudos to Steve for identifying all the questions and Frank for his modern overlay map.
Greg O.
Fairchild FC-2
As listed in the 1906 prospectus, Clarence Mackay was an original director/incorporator of the Long Island Motor Parkway.
Mackay can be seen here to Willie K.'s left during a speech at the Start/Finish line of the 1906 Vanderbilt Cup Races.
Comments
That looks like the Mackey Estate in Roslyn, NY.
I believe the plane is either a Fairchild 71 or Fairchild FC-2. The estate is Harbor Hill owned by Clarence Mackay with the main house in the foreground and the horse stables and garage behind it. I’ll guess the year to be around 1930. Mackay was an investor in and director of the LIMP and as a friend of Willie K., attended the Vanderbilt Cup Races. As the plane is marked “Roosevelt Flying Corporation”, I believe it was based at Roosevelt Field (adjacent to the LIMP) where it was used for flying lessons and training.
mackay estate roslyn
Clarence Mackay’s Harbor Hill estate with Carriage House in today’s East Hills, NY. The estate was built at Nassau County’s highest elevation. Mackay was a Vanderbilt Cup Race official and close friend of William Vanderbilt II. The planes are likely from Roosevelt Air Field, Garden City, around 1920s?