This Month’s Featured Article

The hidden secrets and historic highlights of Hillsdale, NY

By Published On: October 1st, 2016

By Allison Guertin Marchese |

hillsdale2Hillsdale has been a National Historic District since 2009. Yet one of the strangest secrets of Hillsdale’s history is that few facts, names, and general records seem to have been kept, making it very difficult to piece together what really happened back in the beginning. In his History of Hillsdale, New York, printed in Philmont, NY, in 1883, the Hon. John Francis Collins wrote: “The turbulence in Hillsdale for three-fourths of a century after its first settlement by civilized people and the different nationalities of those people has prevented any historic record being kept of them, and their scores of cemeteries, not being under legal protection, have become to a great extent obliterated. For want of historic records a majority of the most prominent inhabitants living in the town a half century ago are now nearly forgotten. Without such records, a half century hence, a majority of the present population of the town will be forgotten or only preserved by our better organized cemeteries.”

Despite Mr. Collins’ gloom and doom assessment of Hillsdale’s past, there are a few rather great highlights.

For everyone reading this who has not been to Hillsdale, it sits on the eastern border of Columbia County, a mere stone’s throw from Massachusetts. Hillsdale is a pretty little town in a pleasant little valley with rolling mounds and sweet summits. To the east is the protective Taghkanic Mountain range made up of rock so ancient it defies reason. Hillsdale is not all broken slate and gravel roads, but has small brooks and streams that run off the main waterway, the Green River, named for the many trout that used to run through it, giving the water a colorful verdant hue. All of Hillsdale’s water runs into the Roeliff Jansen Kill which is the headwaters of Copake Creek. Roeliff Jansen is a legend of sorts in Hillsdale with many buildings and organizations, parks and such named after him in addition to the major River.

Who was Roeliff Jansen?

According to several newspaper articles and histories, Roeliff Jansen was Scandinavian, rather than Dutch as most people thought. His name actually appears with several spellings: Roelof, Rolf, and Roeliff, the one most commonly recorded. There was also a reference to his name, hidden deep in a historical document called the Van Rensselaer Bowier Manuscript where he was referred to as, Roelof Jansz van Masterland. History tells us that he was born in Marstrand in Bohuslän, Norway, around the year 1602, which would make him Norwegian. Several references exist recording Norwegians coming to the Dutch colonies as early as 1617 with references to “Nordman’s Kill” south of Schenectady and “Beverwyk” in Claverack.

Jansen then emigrated with his two daughters, Katrina and Kytje, and his wife, Anneke Jans, whom he had married in Amsterdam. They arrived in New Netherlands on May 24, 1630, by way of a great ship called the “Eeendracht.” Jansen’s purpose in sailing to the New World was to work on the Rensselaerswyck Manor (near what is now Albany), the colonial estate or Dutch patroonship run by Killeen van Rensselaer, a Dutch merchant and one of the original directors of the Dutch West Indian Company (the very same outfit that had earlier employed the famous adventurer and sailor, Henry Hudson).

Under the terms of a patroonship, the patroon or owner had total rule over his land including the creation of laws, churches, and villages. Tenant farmers were allowed to work the land owned by the Manor Lord, but were required to pay rent for the privilege, and essentially the renter had no rights of ownership of the property he farmed. Roeliff earned about $72 per year farming a parcel known as the de Laets Burg farm. He is believed to have lived on the westerly side of Roeliff Jansen Kill in Columbia County, east of Hillsdale.

In addition to farming, he was in the horse trading business, which seems to have been a bit shady with some accounts reporting that it bordered on horse stealing. Apparently Roeliff was also a bad farmer. Van Rensselaer had a certain standard for his tenants, and in a letter written on July 20, 1632, to Wolfert Gerritz, he complained about Jansen. Van Rensselaer is quoted as saying: “bad management that Roeloff Jansen could not get any winter seed. I hope that he has sown the more summer seed.”

In another letter the Patroon wrote on April 23, 1634, to Director Wouter van Twiller, he says, “I see that Roeloff Janssen has grossly run up my account in drawing the provisions, yes, practically the full allowance [even] when there was [enough in] stock. I think that his wife, mother, and sister and others must have given things away, which cannot be allowed.”

Despite his poor skills, in 1632 Roeliff was awarded the title schepens, probably a law enforcement position responsible to the patroon. The job required surveillance of the river fronts along New Amsterdam. The story is told that late one cold winter night, while on his way back to Albany, Jansen was traveling in a krag, a rather thinly constructed wooden boat. Before noticing anything was amiss, the ice around Roeliff’s craft closed in on him and the other men on board. Miraculously, Roeliff was able to walk ashore where they were surprised to find a group of Indians camping at the mouth of a fairly large stream. Roeliff and his crew had no knowledge of the stream and apparently it had yet to be named. As a way of remembering their adventure, the group decided to name the waterway after the schepen or the responsible lawman in charge of the trip. That seems to be how the Roeliff Jansen Kill got its name. A marker placed by the state of New York in 1932 reads as follows: “Jansen Kill Checomingo Kill First named after Roeliff Jansen, overseer of the Orphan Chamber of the Checomingo Indian Tribe.”

Moving from their de Laets Burg farm in 1634, Jansen and his family eventually became associated with the West India Company in 1634. He moved back to New Amsterdam where he received a grant of 62 acres of land on the North (or Hudson) River. This new farm was located in lower Manhattan. Within just a few years of the purchase, Roeliff died. His wife, Anneke, married again in 1638, this time the Dutch Reformed Pastor of the New Amsterdam Church, the well-known Everhard Bogardus. The Jansen farm ownership, however, went into a nearly 200-year-long land title litigation between Jansen’s wife, Anneke and her sister Marritje Jans. Her heirs in 1654 had received a patent, or land grant, on the land, and this patent was confirmed ten years later by the English authorities after they had conquered New Netherland.

In 1671, five of the heirs conveyed the whole farm to Col. Francis Lovelace, then governor of the province of New York. In 1674 the farm was confiscated by the Duke of York, and in 1705 it went over to the Trinity Church. One of Anneke’s sons, Cornelius, had not joined in the conveyance of 1671, and his heirs claimed that his failure to join invalidated the sale. Between 1750 and 1847 there were sixteen or seventeen suits brought against the Trinity Church, but it was finally decided that the Church had acquired a valid title by prescription. In 1909, the last lawsuit was brought by an ancestor of Anneke Jans.

Notable Nobletown

The town of Hillsdale was originally part of the van Rensselaer patent, land which was in both Massachusetts and New York. It was settled sometime around 1750 by immigrants via Massachusetts and Connecticut, as well as Dutch settlers arriving from the north. Among the early settlers were John Tremaine, Nathaniel House, MD, John and David Collin, Joshua Whitney, Benjamin Birdsall, and Harry Truesdell.

Amongst these was Matthew Noble. In Collins’ history, he reports that, “In pursuance of the English grant, Matthew Noble emigrated from Westfield in Connecticut, to Sheffield in 1725, and was the first white settler in that town. Subsequently Robert Noble emigrated from Westfield to [what is now known as] Hillsdale, and was the first white settler in that town. He, with his associates, procured the Indian title to land five miles square, and it was called Nobletown.”

In its early history, inhabitants spent a fair amount of time (often years) squabbling over the town property lines and building roads, creating jurisdictions and districts. After a few more lengthy arguments, the bickering subsided, Robert Noble moved to Great Barrington and Nobletown was split off from Spencertown.

Hillsdale once belonged to The Mahicans

The first inhabitants of the region were the Mahican Indians referred to in some history books as “non-whites” or aborigines. Collier’s history writes this, “The Indians who so kindly welcomed Henry Hudson were the Mahicans, sometimes mistakenly identified with their cousins the Mohegans, whom Cooper immortalized … They were a tribe of the Lenni-Lenapes which means Original People.”

The Wappinger Indians resided south of the boundary created by the Roeliff Jansen Kill, with their territory extending as far south as the island of Manhattan. North of the Kill was regarded as the territory of the Mahicans proper, whose principal village was on the Hudson River (what is today Castleton). Its name originally was “Eskotak” translated it meant the place of the Ever-Burning Council Fire. The boundary of the Mahicans stretched to the headwaters of the Hudson River. These people occupied perhaps 20 different villages in what is now Columbia County.

The Mahicans, like all other Eastern Indian tribes, were damaged from having contact with white settlers. Diseases that they had never been exposed to took the lives of the tribesmen. The introduction of liquor caused many more to suffer. Collier gave this insight to the introduction of alcohol, “In later years their love for the white man’s ‘fire-water’ became an insatiable appetite most destructive as always in its results. No wonder that some called it ‘devil’s’ blood.”

The van Rensselaers bought Indian land which included the whole of Albany, Rensselaer, and the northern reaches of Columbia County for an unimaginably minuscule amount of money. It is unlikely the chiefs who made the deal understood that they were signing over their land ownership, as this was not a concept that they practiced.

The first purchase was in April of 1680, and subsequent purchases were transacted in 1687. In 1685 and 1688, Robert Livingston continued to assume ownership of, and/or actually purchased more land. With nowhere to live, the Mahican Nation moved its Council seat to Western Massachusetts, portion of the Berkshire Hills that border Hillsdale to the east.

By the mid 1700s, the Mahicans had made a peaceful home in Stockbridge in Massachusetts, as well as Schaticook in Rensselaer County, and in northern Dutchess County, south of Pine Plains.

Evidence of the Mahican’s legacy is evident in the name of places, in found artifacts, and in the famous splint baskets made by whites in the Taghkanic hills, an art they learned from the Indians.

General Knox trail marker

Knox was the man that came up with the idea that the cannon captured north of Albany at Fort Ticonderoga be carried by float and sled over 300 miles to Boston in the winter of 1775 to help fortify General George Washington’s troops. Knox and his men travelled over frozen and deeply rutted roads with 80 oxen and 42 sleds on route to Boston carrying dismantled artillery. By January 24, the first cannons were in Albany and the group waited two days for the Hudson River to freeze before they could cross. One cannon was reportedly lost in the Mohawk River, plunging though insufficiently frozen ice.

Past Greenbush, the group encountered vicious snow storms as they inched along the Old Post Road out of Kinderhook and past Ghent and Claverack. After a two-day delay in Claverack mending a broken sleigh, the men followed the trail which runs parallel with today’s Route 23 from Claverack to Hillsdale, or as it was known then as Nobletown.

In Hillsdale is the General Knox trail marker that bears the inscription: Through this place passed Gen. Henry Knox in the winter of 1775-1776 to deliver to Gen. George Washington at Cambridge the train of artillery from Fort Ticonderoga used to force the British Army to evacuate Boston.

Knox’s expedition struggled to ascend the snowy hills of the Berkshires. They made their way through a passage from Nobletown to Monterey, MA. The scene is depicted in the painting by Thomas Lovell The Noble Train of Artillery. Knox wrote in his diary, “We reached No. 1 after climbing mountains which we might almost have seen all the kingdoms of the earth.”

General Burgoyne slept here?

There is also a story that late in the year 1777, General John Burgoyne marched his troops through Nobletown on his way to Boston after surrendering his troops in Saratoga. The Articles of Convention between Burgoyne and American Major General Horatio Gates stipulated, “A free passage to be granted to the army … to Great Britain, on condition of not serving again in North America during the present contest (Articles of Convention, Article II).”

The route, which tracked from Albany to Hartford, included Hillsdale (Nobletown). The prisoners, who were given an opportunity to return to Britain, arrived in Hillsdale on October 22, where some reportedly camped overnight, experiencing a rare early snow.

Columbia Turnpike East Toll House – Route 23 built 1799

Around the year 1799, an effort started to improve the roads from Hudson to Massachusetts. The effort organized and became the Turnpike Corporation. The Columbia Turnpike was created, and it was built to help establish a commercial trade route for goods, namely wool, rye, and wheat.

The Columbia Turnpike was the longest in the state. It ran from the Hillsdale Tollhouse to Hudson. Known to travelers as the East Gate, the Hillsdale Toll House mirrored the West Gate, an impressive limestone Toll House located in the Town of Greenport. Toll Houses were established on turnpikes to bar travelers from passing unless they paid their passage. The money collected was to be used for maintenance of the roads.

The word “turnpike” comes from the fact that the gates on the toll were called “pikes” and these pikes had to be “turned” in order to let the traveller pass through.

The turnpike operated until 1907, when the company’s rights were purchased by the county. The Hillsdale Toll House was a private residence for two generations of the Decker family until it was acquired by Eldena Jenssen in 1970, mother of its current owner, Victoria Jenssen. Though the Toll House is in great need of repair, there is hope that it may soon be placed on the National and State Registers of Historic Places.

Thomas Evans, poet

One of Hillsdale’s most colorful native residents was Thomas Evans. He was a poet and he used his writing skills to adorn his lovely town with the beauty of his prose. Here is one of his works from early 1900s:

Beautiful Hillsdale

“There’s a mountain just south of the village,
And a valley that leads to the west
Where the rays of the sun seem to linger.
When it reaches the high rocky crest
Of the Catskills, away in the distance,
Where the Hudson flows past on its way –
It’s a picture of beautiful Hillsdale
At the close of a bright, Summer Day.
Have you seen the sun rise in its glory
And the flood of the first golden light
When the village awakes from its slumber
And the dewdrops are sparkling so bright?
Do you wonder we go there in summer?
Will you ask why we go there and stay?
Well, come and see beautiful Hillsdale
At the dawn of another bright day.

Soldiers and Sailors Flag Bearer Monument

In 1861, men from Hillsdale gathered at the town square, at what is today Hillsdale’s Civil War Memorial, readying to serve their country for the “Union cause.” Columbia County would eventually send some 2,700 men to serve. New York State sent more men and lost more men in the Civil War than any other state in the Union. The Soldiers and Sailors Monument, a bronze statue memorial is dedicated to those who fought for the Union Army in the Civil War 1861-1865.

The monument was commissioned by John K. Cullin who lived in Hillsdale. The sculpture was created by Edwin E. Codman of Rhode Island and put in place on July 4, 1916. On June 20, 2000, the 13-foot high bronze statue weighing 3,500 lbs. was lifted by a crane off of its 15-foot granite base and gently set down onto a flat-bed truck and sent to Rhinebeck for restoration. The site of this monument is, for many, the symbol of the heart of Hillsdale.

To learn more about Hillsdale’s history, you can contact the Roeliff Jansen Historical Society.


A History the Roeliff Jansen Area, a historical review of five townships in Columbia County, NY, culliChatham Courier THURSDAY. AUG. 14. 1958.

“Indian Tribes” Hudson, NY, Columbia Republican, June 19, 1906

“Laureate of The Milky Way”

D.W. Voorhees, Chatham Courier, Thursday, November 20, 1958

The History of Hillsdale, Columbia County, NY ~ Memorabilia of Persons and Things of Interest, Passed and Passing, by The Hon. John Francis Collin, Ex-M.C., and Edited by Prof. H.S. Johnson, A.M., 1883