Once Upon A Time in Westchester

The History of Westchester Founded in 1683


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By W. Dyer Halpern and Marisa Iallonardo



Opening of new Chappaqua train station_New Castle Historical Society

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The People 

From an accidental river explorer to the first Supreme Court Justice, the many colorful characters from Westchester’s past have helped create a history littered with powerful players and notable names.


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 The Half Moon, courtesy of the Library of Congress LC-USZ62-61745



Henry Hudson




Hudson, courtesy of Stanley L.Klos Henry Hudson.org


Bad weather usually makes people want to stay put. Not Henry Hudson. Thanks to bad weather, he stumbled upon the eponymous river.


A native of England sailing for the Dutch, Hudson was commissioned by the Dutch East India Company in 1609 to find a northern route to the East. Sailing from Amsterdam towards Russia, the 20-person crew of the ship Half Moon hit cold and rainy weather. With the crew threatening to mutiny, Hudson decided to steer the ship west, towards warmer weather.


Hudson and his crew anchored in Manhattan in September, 1609. On September 13, the ship was docked near Yonkers and Hudson made contact with some of the natives when he arrived in present-day Cortlandt. (Records show that, after the Half Moon was docked, one  native jumped on board and stole some clothing and a pillow. When one of the shipmates discovered this, he shot the native, killing him.) Eventually, Hudson and his crew sailed as far north as Albany, and, by October, they were on their way back to England. Failing to find a route East, they docked in Devonshire on November 7.


Hudson attempted to make one final voyage to find his beloved northern route to the East in 1610, but after hitting bad weather once again, his crew was successful in its mutiny. Hudson, his son, and seven other sailors were put in a tiny boat and sent into the ocean. They were never heard from again.


Jonas Bronck

Aprx. 1600-1643


Jonas Bronck, after whom the Bronx River and the
borough of the Bronx were named, was the first white settler to set foot in the county and the first resident to turn his nose up at expensive Manhattan real estate in favor of the comforts of land north of Manhattan. In 1640, Bronck, a Scandinavian, traveled across the Atlantic Ocean in a ship owned by the West India Company. He brought along his family, his farmhands, his farmhands’ families, his servants, his cattle, and other varied goods. Upon landing on Manhattan Island, the trend-setting Bronck decided not to purchase expensive land in Manhattan from the West India Company, as was the popular custom of the day, but to seek out
unclaimed land north of the island. He eventually purchased 500 acres of land from two Native American chiefs, Ranachqua and Taekamuck “lying between the great kill (Harlem River) and the Ahquahung (Bronx River).” It is believed that Bronck then used stone he had brought from Holland to build the first house in Westchester (though, now, in an area officially part of the Bronx). The house no longer exists.


Adriaen Van Der Donck



Adriaen Van Der Donck has the distinction of being the first lawyer ever to serve in the New Netherlands (the Dutch name for New York). He was also the first and only patroon, (a landholder who was granted property rights for bringing 50 settlers to the colony) in the part of Westchester that is now the Bronx and one of the earliest European landholders. He purchased 24,000 acres of land from the Native Americans in 1646. But Van Der Donck’s greatest claim to fame is that he was one of the driving forces behind the expulsion of Governor Peter Stuyvesant, who was deeply intolerant of religious freedom.


 IndianDeed document_courtesy of Scarsdale public Library


Van Der Donck was murdered in 1655, supposedly while defending his home against a Native American attack. But his legacy remains strong in the county. A street named in his honor currently runs through Yonkers, and the Saw Mill River gets its name from the sawmill that was located on Van Der Donck’s property.


The Six Manor Owners


Next time your local mayor or town supervisor gets out of line, just think: it could be worse; he could be your Lord. Before the six cities, 19 towns, and 23 villages sprang to life to make up the Westchester (and part of the Bronx) we all know today, most of the land was divided into six manors, and those who ruled over each of these land segments were referred to as “lords,” landholders who could sell or rent their land to tenants and who could set up local courts to decide local issues. Some Manor Lords also were granted seats in the state assembly.


In Westchester, there were six Manor Lords (their names may ring some bells): John Archer, Lord of Fordham Manor (established 1671); Thomas Pell, Lord of Pelham Manor (established 1687); Frederick Philipse, Lord of Phillipsborough Manor (established 1693); Lewis Morris (future governor of New Jersey), Lord of Morrisania Manor (established 1697); Stephanus Van Cortlandt, Lord of Cortlandt Manor (established 1697); and Caleb Heathcote, Lord of Scarsdale Manor (established 1701).


Together, these six men created the earliest governments in the county and their manors set boundaries that to this day still mark the borders between neighboring Westchester towns. The tenant-farmer system that was created by the birth of the manors also helped fuel the local economy. The men—sorry, no women—who watched over the
six Westchester manors also served as patriarchs for families who
developed great wealth and brought large amounts of capital into the county for years to come. 


Thomas Paine




Thomas Paine_LC-USZ62-5243_Library of Congress


Thomas Paine—writer, patriot, New Rochelle homeowner? It’s true. The author of the 1776 pamphlet Common Sense and the writer of the famous phrase, “These are the times that try men’s souls,” was, in 1784, awarded the 300-acre farm of
Loyalist Frederick Davoue, which stood in New Rochelle. However, Paine apparently did not appreciate the benefits of a Queen City address. He spent most of the 1790s
in France after he became frustrated with George
Washington’s handling of the post-revolutionary period. Acting on an invitation from Thomas Jefferson, Paine
returned to New Rochelle in 1803 and lived there until 1806 when ill health forced him to seek care in New York City. He was buried on his farm in 1809; in 1819, his remains were disinterred and taken to England. A monument in honor of his legacy was built in 1839 and still stands in New
Rochelle. His cottage was named a National Historic Landmark in 1972.


John Jay




JohnJay_Courtesy of the Library of CongressLC-USZ62-50375


What do Westchester mothers want more than anything else? Healthy—and successful—kids. That’s why John Jay would be any county mother’s wunderkind. Born in 1745, raised in Rye, educated at a boarding school in New Rochelle, admitted to King’s College (now Columbia University) at age 14—John Jay got off to a good start, but Jay was more than just an Ivy Leaguer. He was President of the Continental Congress, an ambassador to both Spain and France (where he negotiated the controversial Jay Treaty), contributor to The Federalist Papers (what mom doesn’t love a kid who can write?), Governor of New York (1795-1801), and, most famously, the first Chief Justice of the United States Supreme Court (1789-1795). Jay, despite owning slaves, spoke out against the institution of slavery, and as governor, signed the law that emancipated the slaves in New York State. As early as 1786 he was quoted as saying, “To contend for our own liberty, and to deny that blessing to others, involves an inconsistency not to be excused.”

And as proud a mama as Mrs. Jay must have been, she was probably a pretty proud grandma, too. In 1789, John fathered William Jay, a prominent Westchester resident who served as a county judge for three years and was one of the leading abolitionists in the county.


John Jay retired to the Katonah section of Bedford in a house that still stands on, appropriately, Jay Street; he died at the age of 84. His house in Bedford currently serves as a museum, and both the high school and middle school in the Katonah-Lewisboro school district still bear his name.


Hachaliah Bailey



We bet way more than half of Westchester parents have taken their clown-loving kids to see the Ringling Brothers and Barnum & Bailey Circus. When it comes to town in March, think of Somers farmer and drover Hachaliah Bailey, considered the father of the modern-day circus. (Bailey’s nephew adopted James Anthony Bailey, who became one half of the now famous Barnum & Bailey duo.) On a trip to New York City in 1807, Hachaliah
Bailey purchased Betty, an African elephant. Although he hoped to use the elephant—nicknamed Old Bet—to help with heavy farm work, so many people came to see her, that Bailey began charging an entrance fee. Eventually, he took the show on the road and traveled with the elephant throughout Westchester, upstate New York, and New England.


 Bailey stopped traveling and returned to Somers in the 1820s to begin construction on his now famous 18-room Elephant Hotel, named, of course, for the animal that started it all. Located at the intersection of the Croton Turnpike and Route 202, the brick red hotel, which opened its doors in 1825, served as a prominent hotel of the era, with guests including Martin Van Buren, Aaron Burr, and Horace Greeley.  But all did not end well for Bailey. In 1845, in a tragic twist of fate, Bailey was kicked by one of his horses—and died.


Washington Irving




Washington Irving, 1809,by John Wesley Jarvis_collection of HistoricHudsonValley


How famous do you have to be to have a village and an NBA team named after you (or at least your pen name)? Just famous enough to have written the spookiest Westchester story of all time.


Born in New York City in 1783, Washington Irving had family who lived in the county and was fond of visiting them during the holidays. Irving was fascinated with the area and some of the local residents and, in 1820, he used his fascination to create The Legend of Sleepy Hollow.


In 1835, Irving finally succumbed to the lure (and lore) of the county and moved into a cottage near his nephew’s estate in Tarrytown. He expanded the house that was already on the property and named the cottage “Sunnyside.” While at Sunnyside, Irving hosted numerous parties. Among his literary guests: Nathanial Hawthorne (who is the namesake for the
Hawthorne section of Mount Pleasant), Henry Wadsworth Longfellow, and William Cullen
Bryant. Irving, who never married, lived with his brother Ebenezer and Ebenezer’s five daughters, whom he considered to be his family.


In 1854, the village of Dearman was renamed Irvington by popular vote, in homage to the author (as was Irvington, New Jersey, and Irving Avenue in Port Chester).

But what’s this about an NBA team? Irving wrote the 1809 historical satire Knickerbocker’s History of New York under the pen name Diedrich Knickerbocker. It was then that the term “knickerbocker” began its association with the city, and consequently, served as the namesake for our frequently last-place basketball team.



Daniel D. Tompkins



Born in Scarsdale and educated at the North Salem Academy, Daniel
D. Tompkins was one of the most politically active native sons of Westchester County during the early 1800s. Tompkins had everything a politician needs to be successful.
He had looks—a “face of singular masculine beauty,” as one essayist put it.  He had credentials—Tompkins began his career as a county militiaman and then graduated to the state legislature, where he was a representative for Westchester County. And he had education—he graduated from Columbia University first in his class. But most important, Tompkins had connections, and a good wife—he married Hannah Minthorne, a merchant’s daughter whose father was well associated with Tammany Hall, the early 19th-century political machine. In 1804, he was elected to the United States House of try Representatives—but he never served; he was appointed to the New York Supreme Court the same year. Three years later, he became the state governor.


During the War of 1812, Tompkins proved to be a strong and decisive leader for the state. He even personally paid to fund the militia. In 1816, grateful New Yorkers pushed for Tompkins to be nominated President of the United States. Unfortunately, his name was not known on a national level. He instead wound up as Vice President to James Monroe. But Tompkins’s vice-presidency did not go well. He was in poor health and accused of financial misdeeds. He turned to drink and died in 1825.


James Fenimore Cooper



James_Fenimore_Cooper_by_MathewBrady_ c.1850_Wikipedia Public Domain


Best known as the author of the 1826 smash hit novel The Last of the Mohicans (shame on you if you thought it was just a movie), James Fenimore Cooper’s earlier book, The Spy, was based on stories about Revolutionary War Westchester that he learned from his good friend, John Jay. Interestingly, it
was in The Spy that Cooper credited


Westchesterite Betty Flanagan with the invention of the cocktail. (There are many, many local legends and theories as to the exact origin of the word. One we like is that Flanagan apparently ran out of stirrers and had to use the feather of a cock to stir drinks in her Elmsford bar.) Cooper was not a Westchester resident by birth—he was a Jersey boy—but he moved here after his marriage in 1811 to the daughter of a wealthy loyalist named Susan DeLancey. They settled down in Scarsdale but
eventually left the county for Cooperstown (named after his father, a judge and land speculator), where he died in 1851.


Edgar Allan Poe




E.A.Poe daugerreotype of poe_courtesy of  EdgarAllanPoeMuseum,Richmond,Virginia


Okay, fine, so he didn’t write The Tell Tale Heart or “The Raven” in Westchester, but Edgar Allan Poe did compose poems and short stories while living here. He also died while making his way back to his Westchester cottage—that’s got to count for something, right? Back in 1846, when Fordham was still part of the county, Poe lived in a tiny cottage with views as far as the Long Island Sound. He moved his wife, Virginia, and mother-in-law, Maria Clemm, from New York City to the then-rural area to help Virginia, who was afflicted with tuberculosis. She died in January, 1847. Poe wrote “Annabel Lee”, The Cask of Amontillado (which was made into a movie in 1998), and “The Bells” while living here. The writer died on October 7, 1849, on his way home from Baltimore. Today, the cottage—located on Kingsbridge Road and the Grand Concourse—is maintained by the Bronx County Historical Society, which conducts tours of the house.


Elisha G. Otis




Elisha Graves Otis_Photo courtesy of Otis Elevator Company


Contrary to what many believe, Elisha Otis did not invent the elevator. But he did invent an important part of the elevator—the brake. Born in Vermont, Otis got his start in the mechanical industries in 1845 while working for a bed stand manufacturer in Albany. Eventually Otis moved to Yonkers to work for Maize & Burns, another bed stand firm. While there, he was asked to devise a lift to transfer heavy equipment to the second floor of the factory, one that, unlike previous models, would not fall if the cable holding it broke. His solution: “a tough, steel wagon spring meshing with a ratchet. If the rope gave way, the spring would catch and hold.” In 1854, a year after founding his own company, Otis demonstrated his product on the floor of the Crystal Palace Exposition (part of the World’s Fair) in New York by lifting his elevator off the ground and then cutting the support cable. His sales soared. Otis, who died in the diphtheria epidemic of 1861, left the business to his two sons.


Horace Greeley




H.Greeley reading newspaper_New Castle Historical Society


In the 1860s, Horace Greeley was one of the country’s most sophisticated and intellectual editors, with a world-renowned newspaper under his belt and an upcoming bid for president on the horizon. So while some might have expected the city boy to spend his weekends sipping champagne or schmoozing with power barons, he preferred. . .farming.

He bought 75 acres in Chappaqua in 1851 and would come to Westchester almost every weekend. He chronicled his attempts at farming in the book What I Know About Farming (apparently,

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