Alexander Hamilton & The Poughkeepsie Street Where it Happened


Market Between Main & Church

For...or against? Friend...or foe? Alexander Hamilton saw life in terms of big opportunities and big threats, both of which he tackled head-on. Dutchess County, Poughkeepsie, and Market Street in particular, were the backdrop for such engagements; those he chose, and those that chose him.

The best known local history related to Hamilton is his 1788 argument at the County Courthouse at the corner of Market & Main Streets, in favor of New York ratifying the US Constitution to become part of the new United States. Outnumbered two-to-one by those who favored stronger states’ rights led by New York's powerful governor George Clinton, a handful of Dutchess County delegates changed their votes and gave Hamilton a narrow victory of 30 to 27, the closest victory of any of the ratifying states. But in addition to this signature event, Dutchess County was the site or seedbed and springboard of bitter political rivalries and the country's first (but not last) political sex scandal, all engaging Hamilton as a principal player. The mistress, Maria Lewis Reynolds, who would single handedly end any political ambitions Hamilton had, sprang from deep and prestigious Dutchess County roots.

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Market Street Where It Happened

Above left to right: The County Courthouse has been located at the corner of Market and Main Streets since the court's inception in the early 18th century (depiction: 1804 Dutchess Turnpike Map, courtesy County Clerk). The 19th century George Washington medal commemorates a 1785 visit by Washington to the home of Elias Dubois, the half-brother of Maria Lewis Reynolds who lived near the site of what is today the Bardavan theater (DCHS Collections, gift of Jim & Gina Sullivan). Hendrickson's Tavern (photo is illustrative, no specific drawing exists) hosted many notables including Hamilton, and his political enemies like Thomas Jefferson. The northeast corner of Market and Church Streets (the site of the armory building today)was the site of the Episcopal Church, which gave the street its name.

Hamilton Chapter 01

Ron Chernow, in his landmark book, Hamilton, writes that the mistress that would be the downfall of Hamilton's political career was from Dutchess County. "But little is known about her," he wrote. We set out to address that gap!

Although it became public only seven years later, it was before the end of George Washington’s first term as President, in October 1791, that Hamilton "met" mistress Maria Lewis Reynolds in Philadelphia. The relationship led to the undoing of Hamilton's moral reputation and political ambitions. Maria descends from the founders of Dutchess County, whose homes and major landholdings surrounded the Courthouse in 1788. Maria Reynolds, and her husband James who was complicit in the blackmail against Hamilton, were living in Poughkeepsie, possibly either on or close to Market Street in 1790. Just a year before the fateful encounter in Philadelphia.

The Pedigree of Maria's mother, Susannah Vanderburgh

The names of Maria's maternal ancestors read like a "who's who" of Dutchess County's earliest and most prestigious settlers. Maria’s mother was Susannah Vanderburgh. Maria’s maternal grandfather, Henry, was County Clerk (see signature) and a major landowner in Poughkeepsie village and south.

Van Der Bergh Sig
First marriage: Elias Dubois, 1743

Maria’s mother first married Elias Dubois in 1743. The Dubois owned much land in mid Poughkeepsie and east. Perhaps we could call the oldest son Lewis Dubois, the Mayor of Market St. In 1747, he accepted land in his role as County Justice, that would forever locate the Courthouse at Market & Main. On Market Street he had his home, he sold land for a school, and gave land for an Episcopal Church. As Masonic Grand Master, he hosted George Washington on December 27, 1782, at his home. A younger son, Henry Dubois, ran a store next to Hendrickson’s on the west side of Market Street. Dubois Avenue in Poughkeepsie is named for the family.

Green indicates Dubois-related land on Market.
Photo by Daniel Chase

Above are shown early maps showing the major landownings of the Dubois family from the river east, and the photos show the Dubois family house that stands today (house photo by Daniel Chase).

Second marriage: Richard Lewis, 1758
Susannah Lewis Bible 4w

Maria's mother was widowed when she met and married Richard Lewis, in Poughkeepsie. Son of Thomas Lewis and Anna Maria Vanderburgh, Susanna and Richard were first cousins. After marrying, they likely settled briefly in Poughkeepsie area, possibly near New Hackensack, where their oldest son was baptized in September 1759. 

They moved to New York City by 1764 based on Susannah’s removal certificate from Poughkeepsie:  "Susanna van den Burg, h.v.v. Dirk Lieuwes, met attestatie van Pakeepsie ....  N. York Den 20 Feb. 1764." Their association with the Reformed Dutch Church at New York had begun with the baptism of their daughter, Sara, on 12 Jan 1764. Maria was born in 1768. Richard and Susanna were still in NYC in 1789 when they sold land in Ulster County to Susanah’s son, Henry Dubois in Poughkeepsie. Their daughter Susannah (Maria’s sister) was born in 1761 and went on to marry Poughkeepsie’s Gilbert Livingston in 1779. Much studied by genealogists, Gilbert and Susannah Livingston (the latter Maria's sister) are ancestors of Presidents George H.W. and George W. Bush.  On September 9, 1743, the County's Ancient Documents Collection shows Maria's paternal grandfather, Thomas Lewis of Poughkeepsie, posting 40 pounds bail for the recognizance of his son, Richard Lewis (Maria's father when he was age 15). Richard was accused of attacking and wounding Jacob Van Benschoten, son of Major Elias Van Benschoten, striking him with a wooden club on the face and "other harms…" The Lewis family owned much land in Poughkeepsie’s north as well as on the west side of the Hudson. 

Sep. 9, 1743, Maria's father charged with assault
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Leonard Lewis had vast land holdings on both sides of the Hudson
1730 headstone of Leonard Lewis ~ Poughkeepsie Rural Cemetery

Maria, age 15, married James Reynolds in 1783

Reynolds, born in Orange County plied the Hudson River with a sloop for two years during the Revolutionary War. There are some references that James and Maria were married in Poughkeepsie, and while plausible, we have not found any evidence that this is so. The well-known Reynolds family of 19th century Poughkeepsie, involved in shipping and other business, is not related to this James Reynolds, they arrived slightly later.

1790: Richard, Maria Reynolds, and daughter in Poughkeepsie

The 1790 Poughkeepsie census below, is generally conducted house to house so adjacent names on the list can imply adjacent homes. From the bottom up on three consecutive lines: James and Maria Reynolds had been living in New York City. 1790 was a time of change for them, James took on a new job. And Maria would be in Philadelphia by the following year where she would meet Hamilton in October of that year.

No James Reynolds or Maria Reynolds appears in New York City or Philadelphia 1790 census, leading us to believe the Poughkeepsie reference if to Maria the mistress. James Reynolds is shown with wife Maria. Their daughter, Susan, was five years old at the time. Richard Lewis is Maria’s father. He and James Reynolds had recently sold land to Maria’s half-brother, Henry Dubois. It was probably land holdings that kept Maria involved with half-brothers Lewis & Henry Dubois.  Capt. Abraham Swartwout had two sons who became major advocates of Burr, supporting him after the fatal 1804 duel.

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Above: May 26, 1791 Poughkeepsie Journal makes a brief reference to the trip.

Among the more intense rivalries in Washington's cabinet was that of Secretary of State Thomas Jefferson, who would become President, and Secretary of Treasury Alexander Hamilton, who would not. In May of 1791, Hamilton’s fierce political enemies, Thomas Jefferson and James Madison, announced they were taking a “vacation,” of sorts, on a “botanical tour” up the Hudson Valley and into New England. Jefferson specifically instructed that the "Gazette" which was the political mouthpiece of Hamilton, was delivered along the way while traveling. They sent Jefferson’s enslaved coachman and "waiter," James Hemings (half-brother of Sally Hemings), to Market Street’s Hendrickson’s Tavern with horses and carriage. Jefferson and Madison remained in New York City to dine with Hamilton rivals Aaron Burr and Chancellor Livingston and then headed to Poughkeepsie by boat. When Jefferson awoke on Market Street on May 23, 1791, in keeping with a botanical tour, he noted “The White pine [5 leaved] Pitch-pine [3 leaved] Juniper, a shrub with decumbent stems about 8 f. long, with single leaves all-round the stem, and berries used for infusing gin.” Then the three departed for Claverack in Columbia County, up the Post Road, largely Route 9 today. See "The Northern Journey of Jefferson and Madison" at Founders Online and "Thomas Jefferson Takes a Vacation," American Heritage.

Hamilton's Reported Confession of Faith at Hendrickson's

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Above: Rev. Philander Chase.

Brinkerhoff Hendricksons

Illustrative type of building it has been suggested Hendrickson's Tavern looked like.

Hamilton’s deathbed plea to be accepted into the Christian Church was rebuffed by two different clergy. He had earned a reputation as seeking to reconcile with a Christian faith later in life. When ceremonies around the nation were marking Hamilton’s death with tributes, the Rector in Poughkeepsie’s Christ Church at the time, the Rev. Philander Chase (1775—1852) told a story of a friend who personally heard Hamilton testify to his faith over conversation at Hendrickson’s. Hamilton explained his means of coming to embrace his faith through reading and reflection. Chase became a nationally-renowned Episcopal Bishop and told this story throughout his life. These are the words of Alexander Hamilton, as shared with Rev. Chase by someone who said they were in the company of Hamilton at the time at Hendrickson's:

“Not many months ago I was as you are, doubtful of the truths of Christianity. But some circumstances turned my thoughts to the investigation of the subject, and I now think differently. I had been in company with some friends of similar sentiments in New York. I had indulged in remarks much to the disadvantage of Christians and disparagement of their religion. I had gone further than I had ever done in this way. Coming home I stood late at night on the steps, waiting for my servant. In this moment of stillness, my thoughts returned to what had just passed at my friends and on what I had said there. And what if the Christian religion be true after all? The thought certainly was natural and It produced in my bosom the most alarming feelings. I was conscious that I had never examined it--not even with the attention which a small retaining fee requires in civil cases. In this I hold myself bound to make up my mind according to the law of evidence; and shall nothing be done of this sort in a question that involves the fate of man’s immortal being? Where everything is at stake shall I bargain all without inquiry? Willfully blinding my own eyes shall I laugh at that, which, if true will laugh me to scorn in the day of judgement? These questions did not allow me to sleep quietly. In the morning I sent to my friends the clergy for such books as treated on the evidence of Christianity. I read them and the result is, I believe the religion of Christians to be the truth, that Jesus Christ is the Son of God--that he made an atonement for our sins by his death, and that He rose for our justification.”

Hamilton's Youngest Child Lived in Poughkeepsie

Above: The home, at the northeast corner of Washington and Mansion Streets, and resting place at Poughkeepsie Rural Cemetery, of Alexander Hamilton's youngest son, Philip.

Hamilton Philip Pough 4w
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If, in 1788 while he was arguing for New York State to endorse the US Constitution you had told Alexander Hamilton that his son, Philip, would live in a house a half mile north of the courthouse, he could have only thought you meant his then six-year old son,  Philip. He could not have known, that a year before his own death in a duel, that that son Philip would be killed in a duel in 1801. At the time of Philip’s death, three months into expecting a child, they would name the newborn son Philip. It was this Philip who would come to live in Poughkeepsie at the corner of Mansion Street and Washington Street. Philip died in 1884, and was interred on the 80th anniversary of his father’s deadly duel.

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