Alexander Hamilton & The Poughkeepsie Street Where it Happened

Market Between Main & Church

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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 specifically, and Market Street in particular, provided plenty of both.

Hamilton is best known, locally, for his 1788 argument at the Courthouse at the corner of Market & Main, in favor of New York ratifying the US Constitution. The vote allowed NY to become part of the new United States. Outnumbered two-to-one by those who favored stronger states’ rights, a handful of Dutchess County delegates changed their votes and gave him a narrow victory of 30 to 27, the closest victory of any of the ratifying states.

The bitter political rivalries and derailing of political careers by sex scandals got an early start in our newborn country. Alexander Hamilton was front and center in both.

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. Maria descends from the founders of Dutchess County, whose homes and major landholdings surrounded the Courthouse.

Also in 1791, Burr defeated Hamilton’s father-in-law for the position of US Senator from NY, which intensified Hamilton’s disdain for Burr. Many who played some part in Burr’s web of contempt, which would eventually take Hamilton’s life, were either in the Courthouse, or not far outside its walls.

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.

Again in 1791, in May, Jefferson took what many saw as a political trip disguised as a “botanical tour” up the Hudson Valley. Jefferson asked his slave James Hemings to take horses and carriage to their first overnight stop, Hendrickson’s on Market Street so he and his road trip partner James Madison, reportedly could dine with Aaron Burr in New York City. Jefferson and Madison came up by boat later and traveled with Hemings. Jefferson specifically instructed that the "Gazette" which was the political mouthpiece of Hamilton, was delivered along the way while traveling.

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Please send comments, corrections, ideas, recommended sources to Bill Jeffway at . This is an ongoing project. Do send suggestions ~ Bill

Click image below for Hamilton's County-wide story!
November 1791, Aaron Burr chosen NY's US Senator over Hamilton's father-in-law Philip Schuyler, escalting tensions
MAy 26, 1791, PoJo quietly notes the arrival of Jefferson and Madison in Poughkeepsie
Market Street Where It Happened

Above left to right: Depiction of Courthouse from 1804 Dutchess Turnpike Map, courtesy County Clerk. 19th century commemorative coin issued by local Masonic Lodge to commemorate the visit of Washington a century earlier (DCHS Collections, gift of Jim & Gina Sullivan). The house shown as Hendrickson's is illustrative, no specific drawing exists. The tavern had been described as a converted home, similar to the one depicted. Where Church Street intersects Market would be the Episcopal Church on the NE corner (site of Armory) and school on SE corner.

Maria Lewis Reynolds appears to be in Poughkeepsie in 1790, living with her husband and daughter, and next door to her father

The 1790 Poughkeepsie census below. From the bottom up: 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.

The Very Dutchess Pedigree of Hamilton’s Mistress Maria Lewis Reynolds

Van Der Bergh Sig

Maria’s mother was Susannah Van Der Berg, Maria’s grandfather, Henry, was County Clerk (beautiful signature!) and a major landowner in Poughkeepsie’s south.

Maria’s mother was Susannah Van Der Berg, Maria’s grandfather, Henry, was County Clerk (beautiful signature below!), and a major landowner in Poughkeepsie’s south.

Maria’s mother first married Elias Dubois in 1743. The Dubois owned much land in mid Poughkeepsie and east. Perhaps we could call 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 St. he had his home, he sold land for a school, and gave land for an Episcopal Church (thus Church St., btw!). As Masonic Grand Master, he hosted George Washington Dec. 27, 1782, at his home. See 19th cent. commemorative coin below. A younger son, Henry Dubois, ran a store next to Hendrickson’s on the west side of Market St. Dubois Avenue in Poughkeepsie is named for the family.

Dubois Market Street Land Holdings
Green indicates Dubois-related land on Market.
Dubois Farm Southeast Poughkeepsie
Photo by Daniel Chase

Widowed, Maria’s mother married Richard Lewis (Maria’s father) c. 1758.

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
Click above to access County Ancient Documents Search
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.

Hendrickson’s Tavern

Hendrickson’s Tavern. 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. They sent Jefferson’s slave James Hemings (brother of Sally Hemings) to Market Street’s Hendrickson’s Tavern with horses and carriage. They 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 Market Street Confession of Faith

Hamilton’s Market Street confession of faith. 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.

“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.”