My Family in Washington Irving’s Sleepy Hollow

I began this research with a question that was probably inevitable.

My Anderson and Washburn ancestors had lived in and around Mount Pleasant and Tarrytown in Westchester County, New York. Washington Irving knew that country, too. It was the landscape he would transform into one of the most enduring pieces of American literature, The Legend of Sleepy Hollow.

Had my family known him?

It was an intriguing possibility, but possibilities are not evidence. After digging through Dutch church records, deeds, estate papers, tax lists, census records, military pension files and old maps, I have found no document saying that one of my ancestors met Washington Irving.

What I found instead may be more interesting.

They were already there.

Before Sleepy Hollow Was Sleepy Hollow

The incorporated village we call Sleepy Hollow today carried another name for much of its modern history: North Tarrytown. The village did not officially adopt the name Sleepy Hollow until 1996. But the name itself is much older, associated with the Pocantico valley and the Dutch community that had lived there for generations.

The Old Dutch Church stood at the heart of that world. Farmers came there for baptisms, marriages and Sunday worship. The surrounding lands formed part of the vast Manor of Philipsburg.

This was the world of my Anderson ancestors.

On September 12, 1761, the church recorded the marriage of Daniel Enderson and Wyntje Buys, both born and living in Philipsburgh. Daniel Enderson was the man who appears in the family and later English-language records as Nathaniel Anderson. Wyntje became Levina, or Lovina, Anderson.

Their children’s baptisms followed in the same Dutch records. Among them was Johannes Enderies, baptized October 22, 1765. John Anderson.

A name in an eighteenth-century church book would eventually become one of the threads leading my family out of Westchester and into central New York.

Following the Revolution, the Philipse estate was confiscated because of the family’s Loyalist allegiance, and former manor lands were divided and sold. More than a century later, Westchester historian Paul A. Bourquin reconstructed those old farms from deeds, surveys and records of the Commissioners of Forfeitures.

In Bourquin’s numerical key, Nathaniel Anderson appears as purchaser of a 161-acre farm identified in Bourquin’s reconstruction as tract 84. The number was Bourquin’s research device, not an eighteenth-century lot number.

These were not ancestors living vaguely somewhere in Westchester County. They inhabited the old Philipsburg Manor country around Tarrytown and the Pocantico – the countryside that would eventually become inseparable from Washington Irving’s imagination.

A Landscape Already Filled With Stories

Even before Irving arrived, this countryside had stories enough.

During the Revolution, Westchester County became the dangerous Neutral Ground between British and American lines. Roads and farms around Tarrytown were traveled by soldiers, militia, raiders and civilians trying to survive between two armies.

In September 1780 Major John André passed through this country during Benedict Arnold’s plot to surrender West Point. One name appearing in the wider local militia story surrounding the André episode is Isaac See, a man associated with the Andersons’ Westchester neighborhood.

There is an irresistible historical coincidence. During his secret mission André traveled under an assumed name: John Anderson.

There is no known relationship to my Anderson family. It was simply an alias. But it is difficult for a genealogist not to smile at history’s choice of names.

Then Came Washington Irving

Washington Irving was born in 1783. By then the Andersons had already been part of the Philipsburg community for generations.

As a young man Irving knew and explored the Tarrytown countryside. Years later he transformed that landscape into literature. The Legend of Sleepy Hollow, published in The Sketch Book in 1820, placed its story on the eastern shore of the Hudson at Tarrytown and in the secluded valley nearby.

Irving did not invent the landscape.

He transformed it.

The roads were real. The farms were real. The Dutch church was real. The old families and their traditions were real.

And among those families were mine.

The Anderson Household

By 1811 Nathaniel Anderson was gone, and his widow Levina was dead as well.

Her estate papers provide one of those wonderful moments when genealogy suddenly becomes more than a collection of names. The inventory of Levina Anderson’s belongings was taken on June 25, 1811.

Thomas Kipp served as administrator. Henry Washburn and John Bilyea appraised her property.

Kipp. Washburn. Bilyea. Anderson.

Those names recur in the records of this community – conducting one another’s legal business, appraising estates, witnessing documents, marrying into families and appearing in the same local records.

The estate was valued at about $565. There were household goods, furniture, bedding, cooking utensils and the ordinary possessions accumulated during a lifetime.

Nothing legendary.

Which is precisely why I find it so compelling.

This was the real Sleepy Hollow.

Gilbert Washburn

The Washburn connection becomes clearer through Gilbert Washburn, another of my ancestors.

In 1812, when Samuel Bilyea of Mount Pleasant died intestate, his widow Sarah declined administration and asked that it be granted to Gilbert Washburn, whom the document calls “my Brother.” My family reconstruction identifies Gilbert’s wife, Mary Frances Bilyea, as Samuel’s sister, which could make Gilbert Sarah’s brother-in-law rather than her biological brother.

Whatever the precise usage of the word, the document demonstrates a close relationship. Gilbert was entrusted with Samuel Bilyea’s estate.

Once again, the same families were interacting: Anderson, Washburn, Bilyea and Kipp.

They were not isolated branches waiting two centuries for a genealogist to connect them on a computer screen. They were already connected.

Another John Anderson

The next generation presents a genealogical puzzle, but not an empty one.

Nathaniel and Wyntje’s son John was baptized in 1765. Decades later an older John Anderson appears at the center of the Anderson family that settled in Otsego County. His age, the family property records, the repeated use of “Jr.” for the younger John, and the later deeds all point toward the same family line. No single surviving document states every relationship outright, so that qualification belongs in the research notes.

T he younger man, John S. Anderson Jr., was born about 1792 or 1793. I have not found his baptism. His approximate birth year comes from his own later pension statement.

Those pension papers give us something else: they bring him directly back to Westchester.

John stated that on August 18, 1814, he left Yorktown near Pines Bridge for a rendezvous at Tarrytown. From there his company went to Brooklyn Heights. His service was in the light infantry regiment commanded by Lieutenant Colonel Jonathan Varian, and his account identifies Captain John H. See among his commanders.

Here was the next generation of the family, still moving through the same landscape.

And this was not a family tradition written down generations later.

John told the story himself.

Leaving Westchester

In the years following the War of 1812, members of the Anderson and Washburn families began moving north and west toward Otsego County.

The move did not erase the old Westchester relationships. On June 1, 1824, Gilbert Kipp of New Castle, Westchester County, acting through his attorney William Haight, conveyed land in Otsego County to John S. Anderson of Plainfield.

Kipp and Anderson.

Westchester and Otsego.

The old network had traveled.

The following year, an Otsego deed brought together John S. Anderson, Enos Anderson, Silas Anderson, Leonard Anderson, Elizabeth Anderson and Amy Anderson in the purchase of an eighty-five-acre property in Plainfield. In 1828 another deed identifies John S. Anderson with his wife Lovina – Lovina Branch, not the earlier Levina/Wyntje Buys of Westchester.

The deeds show a family continuing to live and deal in land together.

In 1835 an older John Anderson conveyed a fifty-five-acre farm to Silas Anderson. By April 1839 that John was dead. A subsequent deed from John S. Anderson and Leonard Anderson to Silas described the property as the same farm occupied by John Anderson “in his life time now deceased.”

The language is dry and legal. Underneath it is the passage of a generation.

When Two Families Became One

And then the two strands of this story finally joined.

Stephen Washburn, son of Gilbert Washburn, married Zipporah Anderson, daughter of John S. Anderson Jr. and Lovina Branch.

Neither Stephen nor Zipporah was born in Westchester. Both were born in Otsego County. Their marriage does not prove that their parents had been friends back in Tarrytown, nor does it prove some predetermined family connection stretching across generations.

It shows something quieter.

Two families whose names had moved through the same Westchester community eventually migrated into the same region of central New York.

In the next generation, their descendants married.

The Washburn and Anderson lines became one.

What I Was Really Looking For

When I began, I wanted to know whether my ancestors might have known Washington Irving.

I still cannot answer that question.

Perhaps they crossed paths. Perhaps they heard his name. Perhaps they never encountered one another at all.

There is no reason to turn possibility into fact.

But research sometimes answers a better question than the one we originally asked.

I discovered that my family’s connection to Washington Irving does not depend upon a handshake, a conversation or an entry in someone’s diary.

The connection is the place.

Nathaniel Anderson and Wyntje Buys married in the old Dutch community. Their children were baptized there. Their son John was born into it. The Andersons farmed former Philipsburg Manor land. Their neighbors and associates carried names that recur through estate files, deeds and church records. John Anderson Jr. was at Tarrytown during his War of 1812 service.

Then the family moved on.

Washington Irving gave the old neighborhood another kind of permanence. The people in my records never became literary characters.

They did something much more ordinary.

They lived there.

And Then There Is Zipporah

Genealogy usually begins with names.

Daniel Enderson. Wyntje Buys. Johannes Enderies. John Anderson. Gilbert Washburn. Lovina Branch. Stephen Washburn.

For much of this story, those people survive through ink scratched into church registers, deeds, estate inventories and military papers.

Then, generations into the story, something changes.

There is a photograph.

I can look into the face of Zipporah Anderson Washburn.

She was born far from Westchester, after the family’s migration to Otsego County. She belonged to another place and another generation. Yet behind that photograph stretches a paper trail leading backward through her father John, through the Anderson property in Otsego, through Tarrytown, through the farms of old Philipsburg Manor, and finally into the Dutch records of the eighteenth century.

That is where my search for Washington Irving unexpectedly led me. I went looking for evidence that my family knew the man who wrote The Legend of Sleepy Hollow.

Instead, I found something I can document. Washington Irving made Sleepy Hollow a legend.

My family did not inhabit his fiction. They inhabited something better. The real place from which the legend grew.Instead, I found something I can document. Washington Irving made Sleepy Hollow a legend.

My family did not inhabit his fiction. They inhabited something better. The real place from which the legend grew.