Barons of Broadway #22
In this episode, we head once again to Defendorf Lane at 539 North Broadway in Upper Nyack, named after Civil War Captain Wilson Defendorf. A wealthy real estate developer, Defendorf bought and expanded Major John Smith’s cottage near the onset of the Civil War. He later mustered a company of volunteer troops and served in Virginia. At the time of his death, his obituary declared him the richest man in Rockland County.
After his wife’s passing, the house went to distant relatives. In 1933, Helen Hayes chose the old house as her top pick for a Nyack residence, though she eventually settled on Pretty Penny instead. Judge John J. Reilly, later appointed to the state Supreme Court, lived in the house for 40 years. Sadly, this piece of Nyack’s history was demolished in 1997, and today, three gorgeous riverfront estates occupy the former landing area.
Wilson Defendorf
Born in 1820 in Pennsylvania, Wilson Defendorf became a stepchild after his father’s death. His mother, Jane, remarried Jesse Blackfan, who served as the Surveyor General for Tennessee under President Andrew Jackson. Likely due to political connections, Wilson earned an appointment to West Point in 1835. His classmates included Henry Halleck, who became General-in-Chief of the Union, and Lewis Armistead, who left school after being expelled for hitting Jubal Early with a plate. Armistead later lost his life at Gettysburg. Like Armistead, Defendorf also left West Point, though whether by choice remains unclear. At the outbreak of the Civil War, Blackfan raised a massive flag, 15 by 20 feet, atop an 84-foot hickory pole, as a show of patriotism.
Blackfan’s Vineyard
Jesse Blackfan established one of the largest Nyack vineyards in 1855, where the family, including Wilson, moved. West of North Broadway, Blackfan planted 2,400 Isabella grapes and 600 Catawba, which were rare in Nyack at the time. Dr. Robert Underhill of Croton Hill managed the planting and pioneered growing hybrid grapes at Croton Point, making wine for sale in New York City.
Born in 1820 in Pennsylvania, Wilson Defendorf became a stepchild after his father’s death. His mother, Jane, remarried Jesse Blackfan, who served as the Surveyor General for Tennessee under President Andrew Jackson. Likely due to political connections, Wilson earned an appointment to West Point in 1835. His classmates included Henry Halleck, who became General-in-Chief of the Union, and Lewis Armistead, who left school after being expelled for hitting Jubal Early with a plate. Armistead later lost his life at Gettysburg. Like Armistead, Defendorf also left West Point, though whether by choice remains unclear. At the outbreak of the Civil War, Blackfan raised a massive flag, 15 by 20 feet, atop an 84-foot hickory pole, as a show of patriotism.
Captain Wilson Defendorf Recruits Volunteers
Like Blackfan, Wilson staunchly supported the Union. In August 1862, he raised Company K of the Sixth New York Heavy Artillery, also known as the “Anthony Wayne Guard,” recruiting volunteers from Nyack and Rockland County. He set up headquarters in Nyack’s Union Hall and later in Yonkers, where Nyack residents Raymond, Daily, and Murphy became officers. After adding more volunteers in Yonkers, the company moved to Baltimore, where they defended the Baltimore and Ohio Railroad lines from Confederate raiders. By July 1863, they served as a reserve at Gettysburg and later saw action in nearly every major campaign in Virginia through 1865.
In March 1863, when the company reached Warrenton, Virginia, Defendorf was transferred to the position of quartermaster for the regiment, a role he held for about six months. His obituary notes that he became ill from overwork. In September, he received orders to command Company D of the Tenth Veterans’ Reserve, known at the time as the Invalid Corps, stationed in Tarrytown under Moses G. Leonard. He was honorably discharged in May 1864.
Defendorf Purchases the Smith House
Meanwhile, Wilson launched a successful career as a real estate investment broker. By the time of his death, he owned several three-story brick buildings at the corner of the Bowery and East Fourth Street in New York City.
In 1862, Defendorf acquired the small landing property that included John Smith’s former home. While he was away at war, a large addition expanded the cottage into an L-shaped structure. In the hall stood an old “English clock” from the colonial era, chiming three different tunes alternately every four hours. Defendorf, known as a coin collector, displayed his collection in a cabinet for guests. After the war, he became a member of Post Waldron, No. 82, G.A.R.
In 1864, shortly after leaving the service, Wilson married Mary Roche, an Irish immigrant who arrived in America in 1848 at age 14. Wilson owned a sloop and distributed produce and goods to New York City from Van Houten’s Landing. In 1871, Defendorf traveled to England, with his passport describing him as 5’5” with blue eyes. Whether the trip was for pleasure, business, or to connect with his wife’s family remains unknown.
Life at the Old Smith Cottage
In 1883, Defendorf purchased an additional 14 acres of riverfront property, including the old quarry surrounding the Smith house. That same year, Joseph Hilton, a fellow Baron of Broadway and former Confederate general, bought Riverhook across the street. The two Civil War veterans from opposing sides lived across from each other. Defendorf also purchased from Richard De Cantilllon an 1800-era house on a third of an acre between Broadway and Marion Street at Third Avenue. His brother George, a Nyack businessman, lived there for many years.
Defendorf passed away in 1891, leaving an estate valued at $400,000—around $5 million today. His wife lived in the house until her death in 1929. They had no children. Both are buried in Oak Hill Cemetery.
Judge John J. Reilly
The estate passed to Defendorf’s great-nephew, first to Paul Reilly and then to his brother John J. Reilly. John graduated from Fordham Law School and became a lawyer and a staunch Republican, holding several significant positions, including an appointment by Governor Malcom Wilson (for whom the original Tappan Zee Bridge was named) to the New York Supreme Court. After retiring, he briefly served as an Upper Nyack village trustee and Mayor. In his private life, Reilly was an avid reader of history and an artist and sculptor. He studied at the Rockland Center for the Arts (RoCA), and his sculptures, made from brown sandstone found in his yard, were exhibited there.
A Journal News article from the 1970s noted that Reilly preserved much of Defendorf’s furniture, along with historical items like Defendorf’s battle flag, his discharge certificate signed by General Ulysses S. Grant, a panoramic map of Gettysburg, and his spurs, battle sword, and two Bibles.
John Reilly’s wife, Jane, appreciated living in a historic house, saying,
“The judge and I love it this way, and it is quite comfortable. My home is my hobby.”
Jane Reilly
Jane Reilly died in 1988 and John J. Reilly passed in 1997 at his vacation hime in Naples, Florida.
Photographs of furniture from the Reilly archives. Courtesy of the Historical Society off the Nyacks.
The Legacy of Nyack’s Last Colonial Riverside Cottage
Today, real estate baron and Civil War Captain Wilson Defendorf is mostly remembered for his namesake, Defendorf Lane. The old Smith cottage, the last of Nyack’s original riverside homes, didn’t survive beyond the Reillys. In 1997, the cottage was demolished, and now, three beautiful contemporary houses stand where the old quarry once was.
Barons of Broadway Series
#1 The Magnificent Saga Of Larchdell
#2 Revisiting Underclyffe–A Lost, Gilded Age Mansion
#3 The Adriance Era At Underclyffe Manor
#4 The Flying Dutchman Lands at Underclyffe Manor
#5 The Saga of Rivercliff’s Storied Residents
#6 The Winding Saga of River Hook
#8 The Legacy of Belle Crest: From Clockmakers to Tennis Champions
#11 The Dynamite Baron- Wilson P. Foss Legacy at Under Elms
#12 Atlas Acres – The Botanist in Under Elms’ Garage
#13 The Baroness of Shadowcliff
#14 The Peace Room at Shadowcliff – The Story of the Fellowship of Reconciliation
#15 The Troubled Legacy of Williamson Manor
#16 The Moorings: A Confederate General & the Cottages
#17 The Moorings: A Glimpse into the Clarkstown Country Club Era
#18 The Legacy of Henry Palmer – Nyacks First Baron of Broadway
#19 Glenholme: A Historic Estate’s Evolution & Enduring Charm
#20 From Humble Beginnings to Glen Iris: The Rise of Judge Tompkins
#21 Nyack’s Last Riverside Colonial Cottage – The Home of Major John Smith
Mike Hays lived in the Nyacks for 38-years. He worked for McGraw-Hill Education in New York City for many years. Hays serves as President of the Historical Society of the Nyacks, and Vice-President of the Edward Hopper House Museum & Study Center. Married to Bernie Richey, he enjoys cycling and winters in Florida. You can follow him on Instagram as UpperNyackMike.
Editor’s note: This article is sponsored by Sun River Health and Ellis Sotheby’s International Realty. Sun River Health is a network of 43 Federally Qualified Health Centers (FQHCs) providing primary, dental, pediatric, OB-GYN, and behavioral health care to over 245,000 patients annually. Ellis Sotheby’s International Realty is the lower Hudson Valley’s Leader in Luxury. Located in the charming Hudson River village of Nyack, approximately 22 miles from New York City. Our agents are passionate about listing and selling extraordinary properties in the Lower Hudson Valley, including Rockland and Orange Counties, New York.
