Vanderbilt Cup Races

William K. Vanderbilt Jr.

William K. Vanderbilt Jr. (1878-1944)

Avid auto enthusiast, yachtsman and rich playboy of his day, was the great-grandson of Commodore Cornelius Vanderbilt and creator and driving force behind the Vanderbilt Cup races starting in 1904, and shortly after in 1908, The Long Island Motor parkway.

His vision of International auto racing in the United States to spur American automobile innovation proved to be very successful.

'Deepdale' in Lake Success was his first estate.

Designed by architect Horace Trumbauer and built in 1902, Deepdale was Willie K's home during the 1904-1910 Vanderbilt Cup Races that he shared with his first wife, Virginia "Birdie" Graham Fair (m. 1899; div. 1927)

After the separation from Virginia Graham Fair, in 1910, Eagle's Nest, in Centerport Long Island, became Willie's new home. A Spanish revival designed by Warren & Wetmore, it was expanded extensively during Willie K's stay in the home. After Willie K's death in 1944, and after a rejected offer to Robert Moses, his will stipulated that Eagle's Nest be donated to Suffolk County with a small endowment to get a museum up and running.

In 1950, after second wife, Rosalind Lancaster Warburton passed away, his former estate became the Vanderbilt Museum as which it still survives today.

William K. Vanderbilt Sr.

William Kissam "Willie" Vanderbilt I (1849–1920)

Born into the Vanderbilt's 3rd generation, Willie K. Senior inherited 55 million from his father William Henry Vanderbilt and unremarkably continued in the family railroad business.

Marrying Alva Erskine Smith in 1875 saw the eventual birth of their 3 children, Consuelo Vanderbilt, Duchess Of Marlborough, William Kissam Vanderbilt II, and Harold Stirling Vanderbilt.

This view of Vanderbilt's 'Idle Hour' in Oakdale, Long Island, was the second mansion built on the Oakdale estate. The first home was consumed by fire on on April 15, 1899, while his son, Willie K. II, was honeymooning there with new wife Virginia Graham Fair.

When building this new Idle Hour, to avoid the same fate that befell the earlier mansion, Willie K Sr chose to build the house with steel, brick and limestone.

After Vanderbilt's 1920 death, many of the out buildings became private residences with the main house going through many phases, eventually becoming Dowling College. By 2016, Dowling had closed and the house now sits awaiting its next phase.

August Belmont Jr.

August Belmont Jr. (1853-1924)

Belmont was a partner in Belmont and Company and chairman of the board of the Interborough Rapid Transit Co. and the Rapid Transit Subway Construction Company. He was also the president of the Boston, Cape Cod, and New York Canal Co.

The Belmonts and Vanderbilts had many family ties. August Belmont Jr. partnered with Cornelius Vanderbilt III to establish the Interborough Rapid Transit Company for the construction of the city's first subway. August Jr's older brother, Oliver Hazard Perry Belmont was the second husband to Alva Vanderbilt, Willie K Sr's ex-wife.

'Blemton', or 'Blemton Manor', was August Belmont's estate built in 1865 on Fulton Ave in Hempstead, Long Island, with his older brother O.H.P. Belmont and Alva Vanderbilt Belmont living nearby in 'Brookholt'.

The house is long gone and replaced by the Country Estates Apartments at the location today.

Frederick G. Bourne

Frederick Gilbert Bourne (1851-1919) didn't grow up in a wealthy family like many others in this list. But what he didn't have monetarily, he made up for with drive and determination. Also, an eventual, close friendship with the son of the Singer sewing machine company's co-founder, Edward Cabot Clark, saw Bourne not only join the company, but work his way up to becoming the 5th president of the company in 1889.

His 16 years in that position saw unparalleled growth in the company as well as his commissioning of the now famous Singer Building which had been completed in 1908, after Bourne's departure from Singer.

Designed by Ernest Flagg and built from 1897-1900, 'Indian Neck Hall' was Fredrick Bourne's summer 'cottage'. Indian Neck Hall was located directly next to Willie K. Vanderbilt Sr.'s estate 'Idle Hour' in Oakdale, Long Island.

In 1926, Indian Neck Hall, (often referred to as 'Bourne's Mansion') and estate were purchased and became LaSalle Military Academy. LaSalle existed for many years but eventually did close in 2001. It then became part of St. John's College. It currently is also used as an event/wedding hall.

On a personal note; In the mid 70's, LaSalle ran a day camp for small children in their off summer season. I attended then and had camp experiences that I'll remember forever.

August Heckscher

August Heckscher (1848-1941)

Immigrating to the United States from Germany in 1867, he partnered with his cousin and grew his fortune in the mining business.

His later philanthropy created a children's foundation responsible for many playgrounds in NYC and Central Park, as well as a park and Museum of Art in Huntington, Long Island and much larger park named in his honor in East Islip, Long Island.

'Morse Lodge' was originally built for Tyler Morse in 1909 by Little & Browne in Old Westbury and pictured here under the subsequent ownership of Gustave M. Heckscher as the renamed 'Upland House'. Gustave was the son of August Heckscher.

The house still stands today, and in 2012 was up for sale for $5,785,000.

John Jacob Astor IV

John Jacob Astor IV (July 13, 1864 – April 15, 1912) Prominent member of the Astor family, John was a business magnate, real estate developer, investor, writer, and even lieutenant colonel in the Spanish–American War.

On April 15, 1912, at age 47, Astor sadly perished on the maiden voyage of the ill-fated 'Titanic'. Astor was buried in Trinity Church Cemetery in Manhattan, New York City. Four months after Titanic sank, Madeleine Astor gave birth to his second son, John Jacob "Jakey" Astor VI.

Not on Long Island like many of his contemporaries, John Jacob Astor IV took residence in his estate 'Ferncliff', further upstate in Rhinebeck, NY. Seen here in 1910, The Astor family's 'Ferncliff' was eventually torn down in the 1940's.

The later addition of Ferncliff's sports pavilion was designed by Stanford White and built in 1902. It still stands today in use as an event/wedding hall.

Clarence H. Mackay

Clarence Hungerford Mackay (1874-1938)

Clarence's father, John William Mackay, one of the 3 partners in the discovery of the Comstock Silver load, was the source for Clarence's wealth. Not particularly savvy in financial situations, Clarence was thrust into his father's business when Clarence's older, business-trained brother, John Jr, was killed in a steeplechase accident.

Mackay was chairman of the board of the Postal Telegraph Cable Co., president of the Commercial Cable Co. and Commercial Pacific Cable Co. and held numerous other positions with other companies, but struggled to retain his fortunes in the stock market crash in 1929.

'Harbor Hill' designed by McKim, Mead & White between 1899-1905 in Roslyn, Long Island, was one of the largest homes ever built in the United States, and even by the current, modern list of largest homes ever built, it still stands to this day in a tie at 11th place.

Unfortunately, Harbor Hill was demolished in 1947, when Clarence's son John III, could no longer support the upkeep to his father's tremendous estate.

The Dairy Man's cottage, water tower and gate house still stand today, with the nationally-landmarked gate house currently undergoing plans by the Roslyn Landmark Society, and the Village of East Hills, for restoration.

Harry Payne Whitney

Harry Payne Whitney (1872 –1930)

Born into the prominent Whitney family, Harry attended Yale and Columbia, but never completed his law degree opting instead to go into sports and business.

In 1896, he expanded his wealth when he married Gertrude Vanderbilt (1875–1942).

 In 1904, after the death of his father, he inherited $24,000,000, and in 1917, he inherited approximately $12,000,000 along with the large steam yacht Aphrodite from his uncle, Oliver Hazard Payne.

'Applegreen' was originally built for Harry Payne Whitney and his wife Gertrude Vanderbilt Whitney by McKim, Mead & White c.1902 in Old Westbury as a wedding present from Harry's father, William C. Whitney.

Part of the home still exists, but most was torn down long ago.

Harry Bowley "H.B." Hollins

H.B. Hollins (1854-1938) 

Socially prominent Hollins made his fortune as financier, banker, and railroad magnate. He was responsible for organizing the banking and brokerage firm bearing his name, H.B. Hollins & Co. in 1878. He was also a close friend to William K. Vanderbilt Sr, and close friend and partner to J.P. Morgan.

Located on the edge of the Great South Bay in East Islip, Meadow Farm was a sprawling estate. But following Hollins later bankruptcy, the house was sold and eventually demolished in 2002/03 as part of the Harborview project.

Some remnants still exist around the development named for him in East Islip like this entrance gate to the estate.

Fred J. Wagner

Fred J. Wagner was the premier race starter in the early 1900s including: all the Long Island Vanderbilt Cup Races with the exception of the 1904 race. While not part of the upper wealthy set of individuals rounding out the rest of this list, his prominence at the 1905 and onward races, and the fact his house still stands today, dictated that he should be on the list.

His home designed and built by Gustav Stickley in 1913 in Smithtown still exists and was featured here on this site not long ago. Within the linked post can be seen the Board of Directors lists for many of the races.