Local History

Pine Plains – A Snapshot in Time

By Published On: September 1st, 2023

For many, the name “Pine Plains” evokes a dot on the map while driving along the Taconic State Parkway, but to relegate the Hudson Valley town to a bypassing point on a map is to commit a history lover’s faux pas.

For those who have benignly wandered into that particular offense, and I’m forced to include myself, there’s no time like the present to immediately begin righting this breach of  amateur historian etiquette. For those keeping score at home, the Town of Pine Plains this year celebrates its bicentennial, and those looking to bolster their Pine Plains knowledge base need look no further than Saturday, September 9.

Music, food, games, programs, a visit from historic character Isaac Hunting, fiddlers, and other activities highlight that Community Day/Bicentennial Celebration, while on Friday and Saturday, October 27-28, the Pine Plains Free Library and Little Nine Partners Historical Society will conduct an historic Evergreen Cemetery Lantern Tours fundraiser. In between, a host of other bicentennial activities are on tap. To get all the low-down on what’s what as this yearlong celebration winds down, visit http://lnphs.com/events.

Pine Plains a plenty

So, Pine Plains. What of it? As it turns out, for a town of 2,128 as of the 2020 census, plenty.

There’s no mystery concerning what gave rise to the name: When formed from the Town of North East on March 26, 1823, plains of pines where the village now stands instantly gave rise to the moniker. The best guess is that settlements first sprung up in the area in 1740. Between then and the formal establishment of the town, meetings would be held of what was known as the Northeast Precinct, where various and sundry decisions would be reached, including the ever-critical right of all hogs to run on the common if ringed and yoked.   

Moravian mission

Now, let’s return to 1740, specifically July 16, when Moravian missionary Christian Henry Rauch arrived in New York City, having been dispatched by Moravian Bishop August Gottlieb Spangenberg to preach and convert any native peoples he could find.

Eventually, this would yield what became known as “the first successful mission to the heathen in North America,” according to Philip H. Smith’s General History of Dutchess County, published in 1877. Adds the Little Nine Partners Historical Society, “The establishment of the Moravian mission at Shekomeko in the 1740s remains the single most important event in Pine Plains history. It is also probably the least understood.” Prior to the arrival of the Moravians, here lived Algonkian-speaking woodland people, the Schaghticoke-Mahicans.

Rauch, it might be noted, was likely not expecting clear sailing in his pursuit of Christianizing the Native Americans, having been informed that they were “universally of such a vicious and abandoned character that all efforts for their improvement would be dangerous, as well as utterly in vain.”

It was indeed something less than an auspicious beginning: “In New York at the time was an embassy of Mahican Indians on business with the colonial government, probably regarding some land concerns. Rauch sought out the Indians but found them in a wild, intoxicated condition … They came to understood here was a white man who wanted to come to their village and teach them. Tschoop (Wassamapah), who was one of the chiefs in attendance, is said to have remarked that he frequently felt disposed to know better things than he did, but he did not know where to find them,” according to Out of the Wilderness.

With that, precisely a month after arriving in New York City, Rauch set about working with the Mahicans in what was then known as their village of Shekomeko, later part of Pine Plains. On his first visit, Rauch was treated “with true Indian hospitality,” but things quickly went south. “The next day when he spoke with them he perceived, with sorrow, that his words excited derision; at last they openly laughed him to scorn,” wrote Smith. “He was not discouraged; he persisted in visiting them daily in their huts, representing to them the evils of sin, and extolling the grace of God revealed in Christ and pointing out the way of salvation. In these labors he encountered many hardships. He lived after the Indian manner, traveling on foot from one place to another through the wilderness. Suffering from heat and fatigue, he was often denied even the poor shelter of an Indian hut for refreshment and rest.”

Fortunately for Rauch, the worm began to turn, to the extent that by March 13, 1743, Holy Communion was administered to some of those at Shekomeko, and in July 1743, the new chapel at Shekomeko was finished and consecrated. “At the close of 1743, the congregation of baptized Indians at Shekomeko numbered sixty-three persons,” Smith noted. What led to this change of heart? “It seems that one day Rauch fell asleep in the dwelling of Tschoop, who was greatly astounded that this white man would sleep so soundly and trustingly under an Indian’s roof. Tschoop concluded that such a man must be worthy of hearing. This change of heart cleared the way for Rauch to gain ground in his preaching,” observed Out of the Wilderness.

Today, the Moravian Christian Missionary Monument stands between Halcyon Lake and Conklin Hill. If nothing else, it’s been said, the Moravians intended to give the Shekomeko Indians hope for a better life for their people. The past few paragraphs, obviously, present little more than an on-ramp for a more in-depth look at the fascinating history of the Moravian Mission and the Shekomeko.

The railroad

Along with many hamlets, villages, and towns up and down the Hudson Valley, the railroad – used here generically – came along in the 1800s and connected urban and rural life in dramatic fashion. On the business side of things, farmers were suddenly able to peddle their wares outside the region, and pursuing work outside of one’s immediate area became possible. It also opened up travel opportunities. 

Prior to the railroad, how did folks get about with a trip of any distance? Stagecoach and the use of waterways were primary options. “In 1830,” according to the LNPHS, “the first stagecoach route, with a team of four horses, was established in Pine Plains, carrying both mail and passengers twice a week from Pine Plains to Poughkeepsie, returning the next day. This was along what is State Route 82 and US Route 44 today. It was slow (the average speed five miles per hour), the roads were not very good, and space was limited.”

Let’s not forget that, among the observations at that time was the idea that the train would travel so quickly it would become difficult if not impossible for humans to breathe – and the entire operation surely was the work of the devil.

Early on, two long-distance north-south routes were “built to take advantage of the western trade from the Great Lakes and the Erie Canal. The New York & Harlem Railroad went from Manhattan to Albany through the Harlem Valley of eastern Dutchess County, and the Hudson River Railroad hugged the Hudson River shoreline from Manhattan to Albany. Both lines were completed by 1852,” according to the LNPHS. Efforts in 1833 and 1836 to erect a railroad from Poughkeepsie through Pine Plains to Connecticut had failed, each for the same reason: people wanted a canal instead. What they received was, well, neither.  

Fast forward a couple decades later, and along came the short lines. Following the short-lived Poughkeepsie & Eastern Railroad, incorporated on April 23, 1866, came the Dutchess & Columbia Railroad, which came to life on September 4, 1866, and which ran on 43 miles of track that spanned from Dutchess Junction alongside the Hudson River to Millerton. It was completed by 1869. However, by 1874, foreclosure proceedings had begun on the company – it would be reorganized as the Newburgh, Dutchess, and Connecticut Railroad and ultimately acquire as a nickname “The Never Did & Couldn’t.” Mergers, foreclosures, bankruptcies, and the like would symbolize the early days of railroading in and around Pine Plains.

“During the years of World War I and after,” wrote Victor Westman, “the Central New England Railway considered its main line between Pine Plains and State Line, New York, to be that of the former Poughkeepsie & Eastern via Ancram lead mines and Boston Corners due to its lower grades. Next best was the former Rhinebeck & Connecticut route via Silvernails, Copake, and Boston Corners. The heavy grades over Winchell Mountain via the former Newburgh, Dutchess & Connecticut route from Millerton via Shekomeko became the least desirable.”

Passenger trains out of Pine Plains ceased in 1933, with freight service continuing until 1937. In an odd little twist and perhaps a nugget for potential Jeopardy contestants to file away, in 1938, a scant three years preceding the bombing of Pearl Harbor, the crossing at Pine Plains’ South Main Street was torn up and sold for scrap to the Japanese. 

What was the overall effect of railroading on Pine Plains?

In the words of the LNPHS, “Employment opportunities increased as men and women were able to take the train into Poughkeepsie. Farms expanded: Now that raw milk could be shipped by train, production had to increase to meet demand, which meant farmers had to increase the size of their dairy herds.” The society notes that the Briarcliff Farms “operation most likely would not have relocated from Briarcliff Manor to Pine Plains without the railroad. The railroad also made the Pine Plains hamlet a viable location for Borden’s Milk Company.”

Other industries, such as apple drying and barrel making, grew in popularity. And during the peak railroad years, the hamlet of Pine Plains supported two drug stores, two large hotels and several boarding houses, dry goods merchants and general stores, a boarding school, and multiple entertainment venues. Doctors and lawyers abounded. In the early 1900s, at its peak, 18 trains on three railroads daily traveled in and out of the town.


If one is fixin’ to talk about agriculture in the Pine Plains vicinity, the aforementioned Briarcliff Farms wouldn’t be a bad place to start. In 1907, when Walter William Law endeavored to move his operation from Briarcliff Manor to Pine Plains, he purchased 12 farms on both sides of the Pine Plains-Stanford Road (today’s state Highway 82) about two miles south of the hamlet of Pine Plains, totaling 3,249 acres, as well as other small farms, according to the LNPHS, which added that this action “no doubt transformed the quaint, pastoral character of the region.”

Mr. Law was fastidious about his farm, stocked with a herd of 800 Jerseys, of which 200 were considered “highgrades” and the rest pure bred. “All milk cans, bottles, whatever is used in the dairy, are thoroughly sterilized at a temperature of 212°F before use. The dairy building itself is the model of cleanliness. The cows are milked regularly at 3am and 3pm, and the regulations have to be rigorously followed by the milker, who must don a clean white uniform and cap and clean the udder of each animal before commencing. Each man has charge of about 21 cows – prior to milking each he is mandated to wash his hands. Inside the barns, no laughing, loud talking, smoking, or expectorating is permitted.”

A fun fact: Horse breeding has a long tradition in Pine Plains. Perhaps the most important early American thoroughbred stallion, Messenger, stood here for several years after his part-owner, Cornelius W. Van Ranst, brought him to his Pine Plains farm in 1796. In addition, horse racing was popular in the early 1800s and Pine Plains even had its own racetrack, which was located on the empty lot between Stissing Avenue and Lake Road.

And we’d be remiss not to add a few other Pine Plains noodlings:

• In the late 1800s, the Barnum & Bailey Circus boarded show animals over the winter at local farms for $5 per month per animal, with a circus employee boarding with the farmer for $10 per month.

• Stissing Mountain, the town’s most visible landmark at 1,403 feet, is a unique geological formation, a block of 1.1-billion-year-old Precambrian gneiss “floating” on top of younger shale and sandstone.

• Bootlegger and racketeer Dutch Schultz (real name Arthur Simon Flegenheimer), taking advantage of the area’s isolation, ran an underground distilling operation at Harvest Homestead Farm during Prohibition. It was raided in 1932. Schultz was later gunned down by the mob hit squad, Murder, Inc. at the Palace Chophouse in Newark, NJ, in 1935. He was 33.

And here we are, back in 2023. For a fun-filled, spooky, but nonetheless lively look at some of the folks who made the wheels go around in Pine Plains in the 1700s and 1800s, don’t miss the Evergreen Cemetery Lantern Tours fundraiser on October 27-28 presented by Pine Plains Free Library and Little Nine Partners Historical Society. At least four characters are on tap for the tour:

•William Stewart Eno (1827-1902), a lawyer and president of Stissing National Bank (now the Bank of Millbrook) from 1863-1896. He and his wife built Pine Plains’ grandest home and called it The Pines. 

• Bea Patchin (1881-1989) – her father, Mark Patchin, started Patchin’s Mill, one of the oldest mills in the area. Bea lived to be over 108 years old, and her former home and mill building are still standing today. The mill building has been undergoing renovations by The Friends of Stissing Landmarks and was open for tours this summer. The bridge at Patchin’s Mill was famous for being lined with lit up pumpkins on Halloween that were carved by local kids, young and old. 

• Alfred Brush (1792-1872), who owned the historic Graham Brush house from 1829 until his death. The house still stands in the center of Pine Plains and has been restored and maintained by The Little Nine Partners Historical Society, which holds historic reenactments and other programs there throughout the year.  Alfred was a tailor and instrumental in forming the Pine Plains Baptist Church. 

• Julia Duxbury Slingland Jordon (1887-1976) spent summers at the family home in Hammertown, which still stands today, and winters in New York City, where her father had his office. Her first love was music, and she was an early sponsor of Tanglewood concerts. Upon her husband’s death in 1948, she took over and managed his insurance company for 29 years. Throughout her life she served her community on many boards and was a life member of the Pine Plains Chapter of the Order of the Eastern Star. •

To learn more visit lnphs.com. 

Sources: Vol. 5: Out of the Wilderness. A History of the Hamlet of Bethel in the Town of Pine Plains, New York. “General History of Dutchess County,” Philip H. Smith, 1877. Vol. 4: Pine Plains and the Railroads, Bicentennial Publication, Lyndon A. Haight, 1976. Wikipedia. The Gazette and Courier, Greenfield, MA.