Woodlea: Vanderbilt 'Mansion of Misfortune' now home to Sleepy Hollow Country Club

Woodlea, the 70,000-square-foot mansion on the 500-acre Westchester County estate of Col. Elliott Fitch Shepard's widow, Margaret Louisa (Maggie) Vanderbilt Shepard, is pictured in 1906. The photo shows the extensive formal gardens carved into the hillside on the west (Hudson River-facing) side of the house, which were replaced by a golf pro shop in the 20th century. Woodlea was the 15th largest private home in the nation upon its completion in the 1890s. Mrs. Shepard sold Woodlea shortly after this photo was taken. (Photo courtesy March 1909 edition of American Homes and Gardens magazine, University of Michigan College of Agriculture digital library)

Woodlea, the fabulous Scarborough-on-Hudson Gilded Age mansion and estate of Colonel Elliott Fitch Shepard and wife Margaret Louisa (Maggie) Vanderbilt, was known as the Mansion of Misfortune in its heyday.

Today it is home to Sleepy Hollow Country Club.

The historic property has had long and often tragic history.

Seemingly cursed from the outset of construction in winter 1892, the Shepards' country playground quickly became a redoubt of despair for Mrs. Shepard.

Elliott Fitch Shepard is shown in an 1893 illustration based on an 1890 photograph by Edward Bierstadt. (Illustration appeared on page 427 of The Illustrated American, April 8, 1893 edition)

First, her husband shockingly died on March 24, 1893, some four months into the project. Previously known for his excellent health, Elliott Shepard began suffering sharp abdominal pains and during a stay at the Shepards' Fifth Avenue home in Manhattan, visiting doctors diagnosed bladder stones. Routine surgery was ordered to remove the stones with ether as  anesthetic. Shepard, two months shy of his 60th birthday, was dead within hours.  

Attending physicians said Shepard died from edema and congestion of the lungs but family members insisted he'd been fed before being anesthetized and alleged he was killed by  aspirating stomach contents. For reasons never made clear, no autopsy was performed and no definitive answer has ever been provided.

Maggie Vanderbilt Shepard’s bedroom (shown in a photo published in 1906) was the largest bedroom at Woodlea. (Photo courtesy March 1906 American Homes and Gardens magazine, University of Michigan College of Agriculture digital library).

A second tragedy was to come. Marguerite, the Shepards' 14-year-old daughter, died of complications from pneumonia in February 1895 with Woodlea nine months from completion. Like her late father, Marguerite had previously been known to be in excellent health.

Another family tragedy would come on Nov. 6, 1896 when Maggie's mother Maria Louisa Kissam Vanderbilt, 72, died at Woodlea days after one of the fledgling estate's rare happy moments. Maria had been at Woodlea for the wedding of granddaughter Edith Shepard to Italian painter and photographer Ernesto G. Fabbri on Oct. 27, 1896 and remained at the estate on doctor's rest orders after fainting at the wedding. 

She was on the mend and getting ready for a fresh air carriage ride on Woodlea's many trails when her heart gave out.

Woodlea’s hillside garden featured a fountain pool and great beds of flowers and shrubs. Some called it the Shepards’ hanging garden because of the way it was carved into the hillside just below the house and separated from the western lawns below it by a stone retaining wall that made it appear to be hanging in air from below but kept it a focal point of the house from above looking west towards the Hudson River. (Photo courtesy March 1906 American Homes and Gardens magazine, University of Michigan College of Agriculture digital library)

Maggie Shepard, who had moved into Woodlea in 1895, made it her home for the spring and fall for much of the next six years while also spending time at  family mansions on Fifth Avenue in Manhattan, Newport, R.I., and Palm Beach, Fla., but called Woodlea quits in February 1902 when she gave her year-round, resident Woodlea house staff notice that they'd no longer be employed after June of the same year.

Mrs. Shepard closed the house and retreated to Europe. It doesn't appear she ever returned to Woodlea. She sold the estate in 1905.

Largely because of the family tragedies, Woodlea was referred to as the Mansion of Misfortune, according to the Syracuse Post Standard of April 4, 1911 on the day its last private residential owner, Archibald S. White, announced the end of his six-year marriage to singer and Broadway and silent film actress Olive Celeste Moore.

The original J. Butler Wright house was sold by Wright’s widow to Elliott Fitch Shepard and Maggie Vanderbilt Shepard in 1892 as part of a $300,000 (more than $10 million in 2023), 450-acre purchase when it was known as The Villa. The sales price was a record high for a Hudson River Valley property at the time. The Wrights’ property became the centerpiece of the Woodlea estate. The Wright house is shown in 1931 while it served as the golf and tennis house at Sleepy Hollow Country Club. It was torn down in 1967. (Wikiwand.com)

A HISTORY OF THE ESTATE

Attorney Joshua Butler Wright (March 8, 1812-Oct. 30, 1877, established a Scarborough country estate in 1860 and called it Kelvedon as of at least 1877. The property appeared under the name Weskora on an 1872 map and was later renamed Woodlea and finally The Villa.

It stood just east of Albany Post Road, today's Route 9, and just north of the future Shepard mansion.

Wright, who went by the name Butler, left the estate and main house to his widow Louisa Susan Bradford Wright (May 2, 1826-March 3, 1901) whom he’d married in 1850. Butler Wright retired from his law practice at about the time he built Kelvedon, but remained active in other business ventures.

Woodlea’s columned Echo portico overlooked the estate and Hudson River and welcomed visitors to indulge in its western views. (Photo courtesy March 1906 American Homes and Gardens magazine, University of Michigan College of Agriculture digital library)

Scarborough at the time was known as Weskora. The name Scarborough was adopted in 1864. Native American Sint Sincks (more commonly Sing Sing later) tribal chief Ghoharius originally sold the property and its surrounding area to the Philipse family of Philipsburg Manor in about 1680 with the approval of his brother Weskora, hence the name.

Scarborough was the Yorkshire, England hometown of English post-Revolutionary War immigrant and Scarborough founder William Kemey. Kelvedon was the name of the Wright family manor in Kelvedon Hatch, Essex, England from 1538 to the mid-1930s.

Wright's ancestors appear to have emigrated from the Kelvedon area to Wethersfield, Conn., in about 1660. There likely was a religious split in the family, with the Wrights at Kelvedon professing Roman Catholicism and the Wrights who headed to the new world showing strong Protestant ties. Church deacons and at least one minister were prominent in the early Colonial America Wright family tree.

The main public apartments – drawing room, library/billiard room, drawing room and the like – opened on one side (left in photo) of the main Woodlea hallway lighted by alcove windows (right in photo) while guests trod carpeted floor decorated with live tropical plants and other furnishings. (Photo courtesy March 1906 American Homes and Gardens magazine, University of Michigan College of Agriculture digital library)

Butler Wright's father was Benjamin Wright, chief engineer of two iconic canals that connected the fledgling nation: the Erie Canal and the Chesapeake and Ohio Canal. In 1969, Benjamin Wright was named "Father of American Civil Engineering" by the American Society of Civil Engineers.

Butler Wright was admitted to Yale at 16 but left in 1830 and completed his degree at Rutgers in 1832. He was admitted to the New York State Bar in 1836.

His law office was in Manhattan's Financial District at 63 William Street between Nassau, Liberty, William and Cedar streets ... The property was part of a footprint that was redeveloped as the 60-story One Chase Manhattan Plaza skyscraper in 1961. It was renamed 28 Liberty Street in the 2010s.

Woodlea’s drawing room where visitors might be entertained was ivory-white and gold with paintings above the doors which also featured yellow and gold curtains. (Photo courtesy March 1906 American Homes and Gardens magazine, University of Michigan College of Agriculture digital library)

He and Louisa also owned a home at 171 Broadway at its southwest intersection with Cortlandt Street in the Financial District, several blocks from Wright's office.

The Wright family properties were valued at a combined $300,000 ($6.7 million today) in the 1870 census when Wright, then 58, had been long retired from the law. He listed an additional $75,000 in personal wealth ($1.7 million today) in that same census.

Wright died in Scarborough on the evening of his 65th birthday. His funeral was on Nov. 3, 1877 at Kelvedon and included family-provided rail service for mourners to and from Manhattan.

The library at Woodlea included comfortable furniture for reading, letter writing and

relaxing, bookshelves lining the walls and leather covering the walls above the bookshelves, a coffered ceiling covered in red gold and, originally, a billiards table or plans for one. Obviously intended as a man cave for Elliott Fitch Shepard, he didn’t live to see the room completed. (Photo courtesy March 1906 American Homes and Gardens magazine, University of Michigan College of Agriculture digital library)

NEXT UP, THE SHEPARDS

Elliott Fitch Shepard came from a family that printed money -- literally. But it wasn't until he married into the richest family in America that he had access to the kind of money that makes dreams come true. 

His dream was Woodlea, today's Sleepy Hollow Country Club.

Several of the club's fairways were once the meticulously landscaped lawns and gardens of Shepard's showpiece country estate.

Unfortunately, Shepard didn't live to see the completion of his 70,000-square-foot mansion on 500 meticulously landscaped acres.

The dining room at Woodlea was paneled with mahogany and included a broad tapestry frieze above the paneling and similar tapestry curtains completing the look across doors and windows. (Photo courtesy March 1906 American Homes and Gardens magazine, University of Michigan College of Agriculture digital library)

Scarborough itself lies some 30 miles north of midtown Manhattan on today's Metro-North Railroad's Hudson Line. Since 1906 it's been incorporated into Westchester County's Village of Briarcliff Manor. The area was originally part of the vast Philipsburg Manor holdings of the Philipse family dating from the 17th century Dutch New Netherland colony. It remained in the hands of the slave-holding and slave-trading Philipse family until the American Revolution. It was seized in 1779 by New York's rebel authorities in retaliation for Philipse support of the British cause and was divided into farms.

The railroad made it an easy commute for the gentry of New York beginning with the Hudson River line's opening between Manhattan and Peekskill on Sept. 29, 1849.

The Renaissance Revival mansion that Maggie Vanderbilt and Elliott Shepard named Woodlea featured some 140 rooms, 45 of them bedrooms for family and guests, 16 bathrooms and many rooms for dining and relaxation -- ballroom, dining room, library/billiard room, drawing room among them. It should be noted that when the estate was turned into a country club in 1911, it was reported that 74 rooms were included in what became the Woodlea clubhouse.

The main entry hall at Woodlea was white with mahogany doors and featured a coffered ceiling, massive red rug and carved white marble fireplace as well as a large oil painting on the far left wall. (Photo courtesy March 1906 American Homes and Gardens magazine, University of Michigan College of Agriculture digital library)

The family's bedrooms, bathrooms and dressing rooms were located on the second floor. Guest bedrooms were located on the third floor. The mansion also included a wing with 20 bedrooms for the live-in house staff. 

Other estate staff personnel lived in the gardener's cottage and the upstairs of the carriage house and the larger farm stable which housed many riding horses and workhorses for the gardeners and landscape workers. The carriage house would later be converted to a garage that could house up to 200 cars, it was said.

The Shepard mansion was built for a reported $2 million to $2.5 million (an inflation-adjusted $60 million to $75 million in 2023).

Margaret Louisa Vanderbilt Shepard is shown in an oil-on-canvas portrait titled Mrs. Elliott Fitch

Shepard by artist John Singer Sargent in 1888. She was 43 shen she posed for the portrait.

(San Antonio Museum of Art)

A LOOK AT THE SHEPARDS

Maggie Shepard, eldest daughter of the richest man in America, had inherited some $12 million ($360 million in 2023) upon the death of her father William Henry (Billy) Vanderbilt in 1885. His estate was valued at $200 million ($6.24 billion today), twice the $100 million ($2.63 billion today) he'd been left by his late father Cornelius Vanderbilt seven years earlier.

Col. Elliot Fitch Shepard is shown in his Union army

uniform during the Civil War (1861-65). Shepard

was a Union army recruiter. (Photo by George

Gardner Rockwood, c. 1863)

The Vanderbilt fortune had been built by Cornelius -- nicknamed The Commodore -- beginning in 1810. At 16, he began operating a two-masted flat-bottomed sailing boat called a periauger purchased by his father in which to ferry freight and people between the Vanderbilt family's native Staten Island and lower Manhattan just north across New York Harbor. Cornelius' deal with his father saw father and son evenly split the profits from the ferry business.

This 1873 painting by Seymour Joseph Guy shows the Vanderbilt family in a parlor awaiting departure to the opera in Manhattan. Pictured, clockwise from far left, William Henry Vanderbilt 1821-1885, unidentified boy, possibly Frederick William Vanderbilt 1856-1938, Maria Louisa Kissam Vanderbilt 1821–1896, George Washington Vanderbilt II 1862-1914, Florence Adele Vanderbilt Twombly 1854-1952 and William Kissam Vanderbilt 1849-1920. From left seated right front of table with white blouse, rose skirt, Eliza Osgood Vanderbilt Webb 1860-1936; blue dress, Margaret Louisa Vanderbilt Shepard 1845-1924, Elliott Fitch Shepard 1833-1893, unidentified man, Emily Thorn Vanderbilt Sloane 1852-1946, unidentified woman, Alice Claypoole Gwynne Vanderbilt 1845-1934, William Douglas Sloane 1844-1915 ad Cornelius Vanderbilt II 1843-1899. The venue for New York opera at the time was the 4,600-seat Academy of Music at the corner of East 14th Street at Irving Place. Snubbed by the old money New York elite and denied luxury box seating at the Academy of Music, the Vanderbilt family and their nouveau riche friends would finance and build their own opera house, the Metropolitan Opera House on 39th Street in 1883. The Academy of Music presented its final opera in 1885 and became a vaudeville venue thereafter. (Oil-on-canvas, Seymour Joseph Guy, property of Biltmore Estate, Asheville, N.C.)

Cornelius was quickly nicknamed Commodore by colleagues and business foes because of his skill as a ferry captain. It was a common nickname for small-time skippers at the time, but by the 1830s it was reserved for Cornelius Vanderbilt alone. The Commodore used his profits to expand his business, operating schooners and later steamboats as ferries along the Eastern Seaboard. Soon he was involved in real estate investing and oceangoing transport from New York around Cape Horn, Chile to the West Coast and the California gold fields. Finally, Vanderbilt with his eldest son and eventual successor William Henry, branched out into railroads which would become the focus of the family business, in particular the family-owned New York Central Railroad.

Fortunately for Maggie, half her inheritance was legally tied up in an irrevocable trust, courtesy of her father, keeping it away from her husband's grasp.

Elliott Shepard could do little wrong in Maggie's eyes, but little right in the eyes of many others, including his father-in-law. Shepard came from a working family with some money, but not Vanderbilt-type wealth. His father, Fitch Shepard, was a leader in the business of engraving and printing bank notes and postage stamps.

The Woodlea estate carriage house, also known as a house stable, is shown in a 1902 photo by architectural photographer H. Herbert Sidman with a horse-drawn carriage being driven on the gravel drive at right. The carriage house included space for carriage horses, carriages and tack on the first floor and housing, likely for coachmen or grooms, on the second floor. A much larger stable on the property provided housing for recreational riding and working farm horses Sidman died in 1904. (Photographer H.H. Sidman Co., 147 E. 116th St., New York, N.Y., appeared in Architectural Record magazine)

Elliott was a longtime attorney of no particular renown whose most successful endeavor was as an aide-de-camp to New York Governor Edwin D. Morgan in 1861-62 while Morgan, a major general of volunteers for the Union Army, commanded the federal military's Department of New York while simultaneously serving as governor.

Elliott successfully avoided any hint of danger, avoiding combat duty while serving only in New York State, but he did raise some 50,000 volunteer soldiers for the Union cause, a group of whom from his home Chatauqua County formed the 51st Regiment, New York Volunteers, know colloquially as Shepard's Rifles. He was named a colonel by Morgan and turned down a promotion from President Abraham Lincoln to brigadier general presumably because it could have entailed him filling a battlefield position. His services as a recruiter weren't needed after the Union instituted a draft in 1863.

Morgan introduced Shepard to Margaret Vanderbilt at a party Morgan threw in 1867 and the pair married in 1868.

Woodlea’s working stables are shown in 1902. Today the stables remain in use in conjunction with Sage Hill Farm and Sleepy Hollow Country Club. The two-story building today includes stalls with running water for 47 horses, an indoor all-weather riding ring with glassed-in viewing area, riders’ lounge with fireplace for socializing, men’s and women’s locker rooms and showers, 24 paddocks, two outdoor riding rings – one Grand Prix sized. (Photographer H.H. Sidman Co., 147 E. 116th St., New York, N.Y., Architectural Record magazine)

Shepard went on to co-found the New York Bar Association in the 1870s and three banks in the 1880s, none of which was a major success. Finally, he purchased New York's Mail & Express newspaper from Cyrus W. Field for more than twice its estimated value. It's no accident that the purchase came three years after father-in-law William Vanderbilt's death. All Shepard's major spending appears to have been funded by the inheritance his wife received from her late father.

In addition to Woodlea, the Shepards' impact in Briarcliff Manor can still be felt in the presence of Scarborough Presbyterian Church, 655 Scarborough Road just east of Route 9 and less than a mile north of Woodlea. The Shepards originally bought a roadhouse at that location and turned it into a church in 1892. After the death of ardent Presbyterian Elliott, Maggie paid for construction of today's Spanish Renaissance church (originally called Shepard Memorial Church) in his memory. It opened in May 1895.

So dedicated was Elliott to his religious beliefs that he purchased the controlling interest in Manhattan's Fifth Avenue Coach Company in 1888 to end its Sunday operations and keep the Sabbath.

Maggie funded construction of the church's Parish House in 1908 and the minister's house, or Manse, in 1913, years after she'd sold Woodlea.

Hollywood silent-era screen siren Olive Celeste Moore (1879-1960)

pictured ca. 1910 was given Woodlea as a wedding gift in 1906

by her husband, businessman Archibald S. White (1867-1924), who

became a millionaire in 1899 after selling his salt mining and

distribution business which would be known as International Salt Co.

White divorced Moore in 1918 and Moore went on to remarry

at least twice. The couple had no children and sold Woodlea to wealthy

neighbors William Rockefeller and Frank Vanderlip in 1910. Vanderlip

and Rockefeller reestablished the estate as Sleepy Hollow Country Club.

(Public domain photo)

THE MOGUL & THE STAR

Energy, salt and banking power broker Archibald Sylvester White (1867-1924) and his wife, singer and Broadway and silent screen actress Olive Celeste Moore, bought Woodlea in September 1906 from Maggie Shepard for between $1 million and $1.5 million (inflation-adjusted $33.4 million to $50.1 million in 2023).

White spent the 1890s processing salt in Ludlowville, New York under the corporate banner International Salt Company. In 1899, he was bought out at International Salt for $1 million ($36 million in 2023) and a five-year non-compete agreement and devoted himself to European travel, leisure art and music. 

By 1906 he was back in the game, founding Columbia Gas & Electric Co., jumping into a field in which he had no experience. He hired experts in natural gas and gas exploration, bought up gas fields in West Virginia, ran pipelines into Ohio cities and wooed politicians in Cleveland and Cincinnati into casting their natural gas lot with his company, provided he would cut the prices their residents were paying and could deliver natural gas in unlimited amounts and in a timely manner. 

The Woodlea estate’s former south gatehouse (pictured) is at Sleepy Hollow Country Club’s south gate adjacent to the intersection of Sleepy Hollow Road and Albany Post Road today. This photo looks out toward Albany Post Road, a.k.a. Broadway, a.k.a U.S. Route 9, the property’s entrance. The gatehouse is on drivers’ left-hand side as they enter the club. Vehicles cannot exit the property here. (Wikiwand.com)

He met all the criteria and made a fortune despite shaving more than 50 percent off consumer prices. He made millions off his holdings in the company.

By 1914, he had founded the banking firm White & Co., but left the company in 1917 when enveloped by scandal over his close friendship with Count Johann Heinrich Graf von Bernstorff, Imperial Germany's ambassador to the United States from 1908-1917.

The Scarborough Presbyterian Church, pictured, was paid
for by Maggie Vanderbilt Shepard to honor her husband,
Elliott Fitch Shepard, in the immediate aftermath of his 1893
 death. (https://www.facebook.com/Scarboroughpres/)

White's downfall came when it was discovered that von Bernstorff had been using funds sent from Berlin to sabotage U.S. arms manufacturing and consequently U.S. delivery of weapons to Kaiser Wilhelm II's enemies during World War I while the U.S. maintained its neutrality. 

White's banking firm was involved with some of those Berlin funds, at least $200,000 of which was used by von Bernstorff to fund a pro-German propaganda newspaper he'd purchased in New York in 1915, Fair Play.

This is an aerial photograph of Woodlea c. 1947 by Robert Yarnall Richie looking east from the Hudson River. Note that the original Italianate garden to the left front of the mansion still exists. It would be replaced later by a golf pro shop. (Photo courtesy Robert Yarnall RIchie Photographic Collection, DeGolyer Library Digital Collections, Southern Methodist University and Sleepy Hollow Country Club)

Olive sued for divorce from White (White agreed with the decision and declined to contest it or countersue) in May 1911. White said Olive refused to live with him in their main residence in Cincinnati and he refused to live with her in their home in Paris. She agreed with both statements and filed for divorce in Paris.

For reasons still unclear, the divorce never went through. Finally, White filed for divorce in 1918, citing problems with Olive's "temperament," but more specifically that she was bleeding him dry financially, keeping company with people -- men in particular -- of questionable character. He called them "high class Bohemians."

White added that he had given Olive an annual personal allowance of $12,000 ($400,000 in 2023) but she'd spent between $30,000 and $40,000 a year ($1 million to $1.45 million in 2023), primarily on her "Bohemian" friends who she fed, clothed and sheltered to at least some degree at Woodlea until the estate was sold in 1910. 

Olive ran up other bills which she never paid. In June 1917, she was sued over non-payment of more than $10,000 in clothing from a Manhattan dressmaker.

She appeared on Broadway in 1902 and 1903 in the shows "Robin Hood" and Florenz Ziegfeld Jr.'s "Red Feather." She acted in several silent films as well, the final being "A Tale of Two Cities" in 1917. She remarried in 1918 and wed a third time a few years later.

White died unexpectedly in Santa Rosa, California on Sept. 28, 1924, at the age of 57.

Olive went on to marry at least twice more but faded into obscurity, dying penniless and alone at age 80 in Hollywood in 1960.

This is a view of Woodlea’s Italianate formal garden on the northwest quadrant of the river-facing side of the mansion.(https://househistree.com/houses/woodlea)

AN OFFER THEY COULDN'T REFUSE

When White in 1910 listed Woodlea for sale for pennies on the dollars ($165,000, or $5.2 million in 2023) of what he'd paid for it, business magnates William Avery Rockefeller Jr. and Frank A. Vanderlip Sr. ponied up with eyes on forming what would become the 338-acre Sleepy Hollow Country Club in 1911.

Rockefeller co-founded Standard Oil with brother John D. Rockefeller and owned the adjacent Rockwood Hall estate. Vanderlip was president of what is now Citibank, co-founder of the Federal Reserve System and Assistant Secretary of the Treasury from 1897 to 1901. He owned the nearby Beechwood estate.

Original board members of the new country club included such old money scions as John Jacob Astor IV (who would die in less than a year later aboard the doomed passenger liner RMS Titanic) and Brigadier General Cornelius Vanderbilt III.

The western facade of Woodlea, now the clubhouse at Sleepy Hollow Country Club, is
pictured in a 2014 photo looking east from the Hudson River. (Wikimedia Commons)

The club remains one of the nation's most prestigious today, with members including actor/comedian Bill Murray and author James Patterson.

In addition to golf, the club offers facilities for boarding horses and provides direct access to the neighboring Rockefeller State Park Preserve, with many miles of trails over more than 1,770 acres of parkland that once belonged to the Kykuit and Rockwood Hall estates of brothers William and John D. Rockefeller.