Hidden History of the Lower Hudson Valley: Stories from the Albany Post Road

By Carney Rhinevault and Tatiana Rhinevault

Today's travelers between New York City and Albany are more familiar with the Thruway than with the old Albany Post Road. But for centuries, this was the main highway between the Big Apple and the capital, and many exciting events occurred along its path in the Lower Hudson Valley. The Dutch Philipse family of Sleepy Hollow engaged in piracy, and tales of such misdeeds from the region inspired Washington Irving to write some of his most beloved stories. Later, prisoners used the road as an escape route from the original Sing Sing prison. During Prohibition, a "beer hose" ran through Yonkers, allegedly placed along the route by beer baron Dutch Schultz. With illustrations by Tatiana Rhinevault, local historian Carney Rhinevault uncovers the stories hidden behind the old mile markers of the Albany Post Road.

• Language: English
• Publisher: The History Press
• Release date: May 15, 2012
• ISBN: 9781614238225

Carney Rhinevault

Carney Rhinevault is Hyde Park town historian and the author of The Home Front at Roosevelt's Hometown: Small Town America During World War II. He has researched thousands of deeds, wills, maps and other documents during a long career in surveying and cartography. Tatiana Rhinevault is a graduate of the Art Department of Moscow State University. She and her husband met while working together in 1990 on a joint mapping project for the U.S., British, Canadian and Australian embassies in Moscow.

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Chapter 1

The Philipse Family of Yonkers and Sleepy Hollow

There is a twenty-five-mile stretch of the Post Road from the Harlem River to the Croton River in Westchester County that was once owned by one family, the Philipses. Starting with a large purchase in 1672, Frederick Philipse I began to build an estate, which eventually totaled fifty-seven thousand acres. The Manor of Philipseburg, with its tenant farmers and two giant gristmills at Yonkers and North Tarrytown, made Philipse and his descendants the richest family in New York Colony. In 1685, the manor was bordered by the Croton River on the north, the Bronx River on the east, the Hudson River on the west and the Nepperhan (Sawmill) River on the south. In 1694, the estate boundary on the south moved to the Spuyten Duyuil Creek after another large purchase. However, after all the acquisitions over a 113-year period, the family lost everything because the fourth generation of Philipses chose the wrong side in the Revolutionary War and was forced to escape to England.

FREDERICK PHILIPSE I

As a young man of twenty-one, Frederick Philipse I (1626–1702) sailed with his parents to the New World in 1647, probably on the same ship as the fourth director-general of Nieuw Nederlandts, Petrus Stuyvesant. He soon was the official carpenter and architect of the director-general and became wealthy by trading the raw materials (mostly beaver pelts) of the Dutch colony for finished products from Europe. More than trade enriched Frederick, however. In October 1662, he had the good sense to marry a widow, Margaret Hardenbroeck (1638–1691), who was richer than he was. Margaret brought to the marriage valuable house lots in Manhattan and Bergen, New Jersey, and the merchant ships New Netherland Indian, Beaver, Pearl and Morning Star.¹ She also contributed more than wealth; she was smart and aggressive, and she soon became the real head of the Philipse empire.

Two years after his marriage to Margaret, in 1664, a British fleet sailed into Nieuw Amsterdam Harbor and simply took over the colony in a bloodless coup. Frederick saw no use in fighting the British and pledged his loyalty to the new government, and he was allowed to continue his businesses as if the Dutch authorities were still in charge. He was not only engaged in merchant trade and land ownership, but he also began the unusual business of manufacturing wampum beads, which were the native Indian form of currency. Within ten years of the British takeover, his wealth had increased 400 percent, and he was officially declared the wealthiest man in New York Colony. By 1679, he owned twenty-four merchant ships, which sailed to British ports all over the world.

SUGAR, SLAVES AND PIRATES

Frederick and Margaret could see that the beaver supply was diminishing, while their fleet of merchant ships continued to grow—a problem that required a change of business strategy. By 1674, sugar plantations had expanded on the island of Barbados in the Caribbean, and the Philipses began the triangle trade of food stuffs from New York to Barbados, sugar from Barbados to England and manufactured goods from England to New York. Later, in 1684, a fourth port of call was added: Angola, on the West African coast. There, the Philipse ship Charles loaded 146² black prisoners for the voyage of misery to Barbados. On this first venture in human trade, which took approximately two months, 18 slaves died and were thrown overboard as food for the sharks. Fourteen blacks died in Barbados, but 105 people were sold at auction, netting the Philipses a tremendous profit. The sugar farmers on the island needed a steady supply of laborers, and the Philipses were willing to fill the need. Most slaves would be worked to death or died of new diseases within two years of their arrival.

From the original cargo of the Charles, there were nine slaves still on board for one reason or another. So the Charles set sail again for America and arrived a month later. To avoid custom duties on the slaves, they were disembarked at Westchester County and were put to work at the Philipse Upper Mills in the present-day town of Tarrytown, where the Pocantico River empties into the Hudson River. Thus the Philipse family advanced from slave trading to slave owning.

When Frederick’s sons Adolph and Philip grew to become young men, they engaged in the risky business of privateering. In 1690, the New York governor hired them to raid French ships along the Long Island coast. It wasn’t always easy to identify the prey, so sometimes a privateer would raid the wrong ship from the wrong country and become a pirate. If Frederick’s secret ledgers were anything like the books of other New York merchants of the time, roughly one-third of his business would have been illegal.

Frederick I became embroiled with another famous pirate, Captain William Kidd. It all started innocently enough in 1696 when Frederick I was approached by Robert Livingston about a business deal. Livingston proposed that, with Philipse’s help, he

would fit out a vessel and capture and destroy pirates (along the American coast) and sell the captured cargoes for the benefit of those fitting out the vessel. Lord Bellomont (the governor of New York) approved the scheme and became one of the associates;…and it was whispered that the king was interested in the enterprise. Livingston recommended Captain William Kidd as the commander, and the vessel was fitted out and started on the famous cruise which brought Kidd to the gallows in 1701 and disgrace to his backers. ³

Naturally, each of the backers blamed the others. Lord Bellomont remarked that: ‘If the coffers of Frederick Philipse were searched, Captain Kidd’s missing treasures could easily be found.’⁴

MARRIAGES FOR MONEY

As evidenced by the slave trading, privateering, smuggling and evading of custom duties, the Philipses’ businesses were not built on ethical or moral principles. Neither was their private life. Frederick I and Margaret married for money, and in 1692, one year after Margaret died, sixty-six-year-old Frederick again married a rich widow, Catherine Van Cortlandt Dervall, who was twenty-six years younger than him. Catherine’s dead husband was John Dervall, also a successful merchant. Catherine’s brother, Jacobus, had married Frederick’s stepdaughter, Eva, one year earlier. As the saying goes, money marries money. Later generations would see a Beekman, a Robinson and a Morris (all from rich families) marry into the Philipse family.

KINGS BRIDGE AND THE POST ROAD

There were only three spots on the early Post Road where a toll was imposed on a traveler: the King’s Bridge, the Croton River Ferry and the Greenbush to Albany Ferry. Frederick Philipse I built and controlled the King’s Bridge by virtue of his ownership of the adjacent lands on either end of the bridge.

King William and Queen Mary had looked for many years for new ways to raise revenue in their New York colony, and they were advised to build a toll bridge at the north end of Manhattan Island at the ford in the Spuyten Duyvil Creek.⁵ New York City was growing rapidly, and the ford was the only entry to the island by horse or foot. One major problem existed, however—when tides from the Hudson and Harlem Rivers rose once a day, the ford was impassable. A bridge could be built, but the King and Queen judged that the construction expense would be too great.

So a new tack was taken—have a private citizen build the bridge, use it to spur development north of the city and collect taxes from the new residents. In 1693, Governor Benjamin Fletcher, on behalf of the King and Queen, granted a royal charter to Frederick Philipse I, which gave him the right to call his estate the Manor of Philipseburg and all the privileges that went with the title Lord of the Manor. One of the privileges was the right to build and charge tolls on the King’s Bridge. Philipse gained a tremendous moneymaker, and William and Mary got their development bridge. Philipse paid a minuscule sum of four pounds, twelve shillings each year for the right to operate the bridge.

King’s Bridge.

The bridge approaches were built by Philipse’s slaves and were made of laid-up stones. The actual river span was made of wood planks. At each end, a gate was placed across the road, and a traveler in either direction would be charged three pennies to cross. The pennies very quickly added up, and the bridge had paid for itself in less than two years. Not until 1759, when the farmers free bridge was built by Benjamin Palmer and Jacobus Dyckman,⁶ did the Philipse cash cow run dry. The bridge was finally removed in 1913 during the construction of the shipping channel between the Harlem and Hudson Rivers.

FARMING, FLOUR MILLS AND SHIPPING

Even though the King’s Bridge was a good source of income, it was only a small cog in the Philipse economic engine. The biggest revenue generator was the farm-to-market system, which had been set up by Frederick and Margaret. Gristmills were built at the Pocantico (at Tarrytown) and Nepperhan (at Yonkers) Rivers, where the rivers’ final descents into the Hudson could turn giant stone wheels to grind wheat into flour. The Philipses collected rent from hundreds of tenant farmers, sometimes in the form of part of their wheat crop. The Philipses also charged a fee to all farmers to use the mill. Coarse flour from the mills would then be sent on Philipse barges from the Pocantico and Nepperhan Harbors to a Philipse bolting (processing) plant in Manhattan, where chaff and bran was removed from the rough grain.⁷ The final commodity of fine flour would then be carried by Philipse ships to England.⁸ There, it would be traded for finished products to be sold in America. Every step along the way created huge profits for the Philipses.

PHILIPSE MANOR HALL IN YONKERS

Frederick I built a magnificent manor house for his family at the Nepperhan mill and a smaller mansion at the Pocantico mill. He was able to enjoy his lavish lifestyle for twenty years, until his death in 1702. Insight into the lifestyle of a colonial manor lord can be gained by visiting both of Frederick I’s mansions. Since being auctioned off after the Revolutionary War, the manor house at Yonkers has seen many changes. Benson Lossing (1813–1891), a famous historian and sketch artist from Dutchess County, had an opportunity to visit the house in 1866. He wrote:

Philipse Manor Hall in Yonkers.

The chief attraction at Yonkers for the antiquary is the Philipse Manor Hall, a spacious stone edifice, that once belonged to the lords of Philipse Manor. The older portion was built in 1682. The present front, forming an addition, was erected in 1745, when old Castle Philipse, at Sleepy Hollow, was abandoned, and the Manor Hall became the favourite dwelling of the family. Its interior construction (preserved by the present owner, the Hon. W.W. Woodworth, with scrupulous care) attests the wealth and taste of the lordly proprietor. The great Hall, or passage, is broad, and the staircase capacious and massive. The rooms are large, and the ceilings are lofty; all the rooms are wainscoted, and the chief apartment has beautiful ornamental work upon the ceiling, in high relief, composed of arabesque forms, the figures of birds, dogs, and men, and two medallion portraits. Two of the rooms have carved chimney-pieces of gray Irish marble. The guest-chamber, over the drawing-room, is handsomely decorated with ornamental architecture, and some of the fireplaces are surrounded with borders of ancient Dutch tiles. The well has a subterranean passage leading from it, nobody knows to where; and the present ice-house, composed of huge walls and massive arch, was a powder-magazine in the olden time. Altogether, this old hall—one of the antiquities of the Hudson—is an attractive curiosity, which the obliging proprietor is pleased to show to those who visit it because of their reverence for things of the past.⁹

The attic is enormous and supposedly could provide living quarters for fifty house servants, some of whom were slaves.

According to John Zukowsky in his 1985 book Hudson River Villas, since the time of Mr. Woodworth,

the manor was acquired by a succession of owners and even served as a rooming house. In 1868 the village of Yonkers purchased it for its first city hall, the city of Yonkers being incorporated in 1872. During that period architect, John Davis Hatch, remodeled a portion of the east wing’s upper stories into a hammer-beamed meeting room. Other additions of this epoch include the 1891 Civil War monument by architect George Mitchell, located on the lawn in front of the east façade. The building served as the city hall until 1908. Since then it has been owned by the State of New York, and today it is open to the public as a museum.

The cellar of the mansion was built by Frederick I as a sort of bank vault for his valuable trade goods. The inside was dry and coated with expensive tiles from Holland. It was the perfect place for Philipse to hide the contraband goods that were often shipped past customs in New York City directly to his harbor where the Nepperhan emptied into the Hudson.

Probably the most dramatic change to the Yonkers estate is what has happened to the Nepperhan (Sawmill) River. In the late 1800s, it was decided by the Yonkers government that the river had become so polluted upstream that the only way to fix the problem was to bury the river in a massive culvert. Where the Philipse mill and dam once produced flour, now there are two one-way streets separated by a park.

CASTLE PHILIPSE IN SLEEPY HOLLOW

The Upper Mill at Tarrytown also had an adjacent manor house with a surreptitious storage cellar. The manor hall included two kitchens, two bedrooms and a full-length attic for temporary storage of grains at times when the mill was backed up with jobs. There was a massive chimney in the center of the house, which serviced the building’s five fireplaces. All in all, the building was probably a tremendous firetrap, but there is no record of it going up in flames. Benson Lossing also wrote about the Upper Mill:

Philipse dam in Sleepy Hollow with Philipse Castle in the background.

We have observed that the Po-can-te-co, flowing through Sleepy Hollow, spreads out into a pretty little lake above an ancient and picturesque dam, near the almost as ancient church. This little lake extends back almost to the bridge in the dark weird glen, and furnishes motive power to a very ancient mill that stands close by Philipse Castle as the more ancient manor-house of the family was called. The first lord of an extensive domain in this vicinity, purchased from the Sachem Goharius, in 1680, and which was confirmed by royal patent the same year, was a descendant of the ancient Viscounts Felyps, of Bohemia, who took an active part in favour of John Huss and Jerome of Prague. Here, at the mouth of the Po-can-te-co, he erected a strong stone house, with port and loop holes for cannon and musketry, and also a mill, about the year 1683. Because of its heavy ordnance, it was called Castle Philipse. At that time the extensive marsh and meadow land between it and the present railway was a fine bay, and quite large vessels bore freight to and from the mill. Here, and at the lower manor-house at Yonkers, the lords of Philipse’s Manor lived in a sort of feudal state for almost a century, enjoying exclusive social and political privileges. The proprietor in possession when the war for independence broke out, espoused the cause of the crown. His estates were confiscated, and a relative of the family, Gerardus Beekman, became the purchaser of the castle and many broad acres adjoining it. In that family it remained until the spring of 1860 (about three quarters of a century), when Mr. Storm, the present proprietor, purchased it.¹⁰

Today, Philipse Castle is owned by Sleepy Hollow Restorations and is open to the public.

THE PHILIPSE STONE CHURCH

Frederick I and his second wife, Catharine, built the fine Dutch church that still stands today a few hundred feet east of Castle Philipse on the banks of the Pocantico River and next to the Post Road. There is a local legend that construction of the church was proceeding slowly whenever Frederick could spare a few slaves from the adjacent gristmill at Castle Philipse. At the same time, the dam at the mill was periodically being washed out by floodwaters at an alarming rate. One of the Philipse slaves had a dream that the Pocantico River would frequently destroy the dam until the church was finished. Old Dutch settlers, including Frederick, were generally superstitious, so work on the church was given top priority, and miraculously, the dam has held ever since. The old Dutch church was the scene of an episode in Washington Irving’s Legend of Sleepy Hollow. Ichabod Crane, as he was being chased by the Headless Horseman, thought that he had reached the sanctuary of the church after crossing the Pocantico bridge. The Headless Horseman, however, vanquished poor Ichabod by flinging his detached head at the hapless schoolteacher.

Church built by Frederick Philipse I, now the oldest church in New York State.

Irving described the church in his typical, colorful and fanciful manner:

A weathercock graced each end of the church. One perched over the belfry, the other the chancel. As usual with ecclesiastical weathercocks, each