Where Cobwebs Thrive on Manhattan Isle

by Cole Thompson

When New York Tribune reporter Eleanor Booth Simmons explored the hills of Inwood and Washington Heights in 1921 she discovered a quaint country community rapidly being swallowed by the big city. In this article she gives us a guided tour of the still standing homes of once rich and powerful families including Nathan Straus, James Mcreery and C.K.G. Billings, to name a few.

A quick author’s note: The first sketch accompanied the article as it appeared in 1921. Other photos I have added myself to provide visuals to Simmon’s prose.

Where Cobwebs Thrive on Manhattan Isle, by Eleanor Booth Simmons, New York Tribune, November 6, 1921.

Where Cobwebs Thrive on Manhattan Isle illustration
Do you like to dream about old houses? Do you like to investigate neglected mansions of a past age, picturing the life that flowed through the high-ceilinged rooms now so musty and decayed?

If you are a New Yorker it isn’t necessary to travel to New England to indulge in this pastime. Forty minutes by subway from the shopping district, a brief walk, and you are in a region of old houses. Some crown the green hills of Inwood, which downtown excursionists are beginning to discover, and some, stranded on the streets, are rudely shouldered by modern apartment houses of glaring brick. But there they are, and in some of them you will find white-haired men and women whose talk takes you back to a day earlier than that in which the characters of Edith Wharton’s “The Age of Innocence” lived.

Inwood Valley, looking north from Fort George near turn of the Century.

Inwood Valley, looking north from Fort George near turn of the Century.

Fancy going into a house a few steps from the Dyckman ferry and finding two brothers and a sister who have dwelt there sixty years! These are the Flitners, children of the Maine sea captain, who, landing at the Hudson River dock with barges of lumber from the North, was so charmed with these shores that he brought his family here to live. Get them talking and they tell you of a time when there were but seven buildings above 187th Street east of Kingsbridge Road. In their childhood the winter skating was the social event of the locality.  Tubby Hook on map 1885 plate 32The lads damned up a brook that ran just north of Inwood Street, now Dyckman Street, and made a wide pond between two small hills. At night they lighted fires of Tar barrels and waste wood on the banks, and the community gathered and sang and shouted and did marvelous things on the ice. Perhaps the winters were colder then, for, as Charles Flitner remembers it, there was always ice from fall to spring.

The Flitner house is well preserved. But just above it, at the first turn of Bolton Road, is a square red house of spacious rooms and staircases of noble lines going to rack and ruin in a way one hates to see, all the more because it is a common story in these parts.

Fort Washington railroad station near turn of the centuryOld inhabitants say it was the policy of the New York Central that left Tubby Hook, as Inwood used to be called, in a forgotten pocket between two rivers, unpeopling the beautiful houses and abandoning them to ghosts. In 1871 that railroad diverted its trains, save one or two slow locals, from the Hudson River tracks to the east bank of the Harlem. Not till 1900 did the first trolley cars run to Kingsbridge, and it was five years later when the subway was extended to Dyckman Street. For a good many years this most attractive part of Manhattan Island was rather inaccessible, except for the men who could afford their horses.

In 1844, when Samuel Thomson, wealthy man of affairs, built the little church that still stands at Broadway and Dyckman Street, men were content to be leisurely. Tubby Hookers who went to business by the 7:53 gossiped in agreeable groups on the station platform till the conductor decided that there were no more tardy passengers to arrive. Elegant ones drove to the city over the Bloomingdale Road, a shaded street that ran down Breakneck Hill past the Hamilton Grange, and those who remember it say it was a fine sight to see the elder James McCreery, the merchant prince, coming down from his home at the end of the River Road, “The last house on Manhattan Island,” behind his team of spanking bays. But Tubby Hookers grew tired of depending on horseflesh and the infrequent trains, and one by one they moved away from their mansions and their landscaped gardens.

Fort Tryon in the early 20th Century.

Fort Tryon in the early 20th Century.

In 1796 Mount Washington was the popular name for the whole range of hills from Manhattanville to Spuyten Duyvil, and traces of the outworks of Fort Washington are to be found from end to end of them now. But as time went on the upper section became known as Tubby Hook, perhaps because the Dutch sailors who went up the Hudson, and who called every point of land a “hook,” saw in the bay of the Spuyten Duyvil a resemblance to a tub, with the steep wooded hills for sides. Isaac M. Dyckman and William B. Isham and the Vermilyea, Nagle and Post families, who among them owned most of the rich lowlands to the eastward, always spoke of their “farms at Tubby Hook.” Then Inwood became the name of this region and the hills to the south Washington Heights. But it is all one chain of beauty, and for years men like Reginald Pelham Bolton, its staunch defender and preserver, and George Barnard, whose studio stands high on “God’s Thumb” above the Hudson, have been saying to City Hall:

“See here! In the wooded hills and slopes that line the water from Jeffrey’s Hook, at 177th Street, to Spuyten Duyvil, New York has the most wonderful potential pleasure ground that city ever had. Purchase it, improve it, preserve it for all time to come.”

 1905 postcard showing P.S.  52And first the Board of Estimate and Apportionment would say: “We will.” And then it would say: “We can’t. Out constituents would not let us spend so much money.” It has pursued, in short, a policy that has kept wonderful residential possibilities from becoming anything more. Who wants to spend money restoring old houses or building new ones when or where Father Knickerbocker may lay out his parks and roads?

However, the slow development has had one advantage. It left sleeping below the surface of the Dyckman Valley evidences of Indian life—native tools and weapons and remains of the dog burials of the redmen of 300 years ago, that Mr. Bolton and W.L. Calver and other ardent excavators might find them for museums of today.

1879 Railroad Map showing Inwood HillHalf a block east of the ferry Prescott Avenue, a narrow unpaved way, runs from Dyckman Street over Inwood Hill. Upper Bolton Road starts from Prescott Avenue just above Dyckman and goes windingly first west, then north, then east. Here is where bankers, lawyers and editors of past generations had their country seats. On the slope between upper Bolton Road and Prescott Avenue and lower Bolton Road, or the River Road, which starts at the ferry, was the estate of Samuel Thomson, who came to tubby Hook in 1835 and who was so ardent a republican that he quarreled with his wife’s titled relatives because he would not say “my lord.” A son-in-law, Walter Carter, publisher, has left this description of his first drive up Bloomingdale Road to the Thomson grounds and of seeingSamuel Thompson - 1st church elderMr. Thomson reading the Bible of a morning “with a beaming face.” He was a good churchman and built Mount Washington Presbyterian Church on his own grounds because he was so sorry to see his neighbors working in the fields on Sunday. But he was also a keen businessman, as was shown by his buying 100 acres of land for $27,500 and shortly afterward selling one acre to J.B. West for $25,000. Three of his ten children became bank presidents, and the eldest, William A. Thomson, was for sixty years an officer of the Merchant’s Exchange Bank. Not a trace of the Thomson mansion remains, and on its site, where the House of Mercy stands, the new Jewish hospital is to be built.

Origional Mt Washington Church -1923- Tubby Hook- built on site of old Black Horse Tavern-But if the Thomson house is razed, many others remain, some of them seeming to shrink back from the steep cut of Dyckman Street and to look down disapprovingly on the noisy traffic the ferry has brought. The old home of Captain William H. Flitner is at 17 Bolton Road. The Rev. Dr. George S. Payson, pastor of the Mount Washington Church for forty years and more, records that the Captain was away much of the time “sailing the seven seas,” but his wife, Louisa, made his house “the abode of peace and gentleness.”

On its door today on sees the words “Dyckman Library.” It seems that Mrs. Alexander Hamilton, who was Elisabeth Schuyler, at her death left some money to establish a free school in the upper end of Manhattan Island. Before the request could be carried out the city inaugurated its public school system, and the money was invested in Broadway real estate. By an act of the Legislature the land was presently sold and the proceeds used to found a library, of which the three remaining members of the Flitner family—Charles, Clara and the Counselor—were given charge. Charles and Clara long taught in the school on Academy Street, which is now George Washington High School, but now they take turns serving in the library, which seems surprisingly modern, with its new books and magazines, in the quaint old house.

House of Mercy on Inwood Hill (later the Society for the Prevention of Cruelty to Children).

House of Mercy on Inwood Hill (later the Society for the Prevention of Cruelty to Children).

Passing the falling-to-pieces red house on the hill, the home of the Talcott family a half century ago, and passing the modern House of Rest for consumptives, one comes to two large frame houses in the bend of the road across from the large brick buildings where the Society for the Prevention of Cruelty to Children now has its shelter, and the Chapel of St. Mary’s crowning the hill. Once there were three frame houses, but one of them was burned.

1884 self portrait of Puck magazine founder and Inwood Hill Resident Joseph Keppler.

1884 self portrait of Puck magazine founder and Inwood Hill Resident Joseph Keppler.

In the beautiful one still standing in the corner Joseph Keppler, one of the founders of “Puck” once lived. For a long time it was vacant, and peering in at the windows one could see fragments of old furniture, and imagine, at twilight, no end of ghosts. In the night you could hear howling, most gruesome—howling of masterless dogs that had taken refuge in the caves of the valley below. Now the Keppler house is inhabited by a family named Friedauf and numerous children romp under the great apple trees and copper beeches on the lawn, and behind the lattices where straggling roses grow. But the paint is scaling, the glass of the great bow windows is breaking and the hand of decay is everywhere.

Straus residence on Bolton Road

Straus residence on Bolton Road

The old Nathan Straus homestead is further along, on a noble slope overlooking the Hudson.Isidor and Ida Straus around 1910 It must have been a charming place in its prime, but it is in a melancholy state of dilapidation now. Still, there is a policeman living in it, very happily apparently. He is a fresh air enthusiast, and, not satisfied with the ozone that must enter through the cracks of the old house, he parked his two infant sons day and night for many months on the roof of the wide veranda. Stern signs, “Beware of the Dogs,” surround the Nathan Straus home, but if you are brave enough to pass the signs find the dogs that are playing with the apple cheeked youngsters are most amiable and waggy of tail.

Across the road from the big house, if you penetrate the thicket of sumac, you will find the stone foundations of the Straus stables. The stables are gone and their foundations are grassy terraces held up by lichened stone. There are traces of an ancient kitchen garden and grape arbor, and it is a delightful place to picnic, with great trees lifting their heads from the steep slope below, and the Ship canal beyond, thick with rowboats and motorboats and darting canoes.

McCreery House

The Inwood Hill home of dry goods magnate James Mcreery

Detail from 1879 railroad map To reach the McCreery house you retrace your steps to the House of Rest and then, if you don’t care to plod to Dyckman Street, scramble down a narrow path to the River Road. Walk north, past overgrown terraces and box hedges, and quaint houses with cupolas and pillars, with the river and the railroad tracks below, and at the end of the path—it is hardly more than a path, though an automobile might negotiate it—is the home of the founder of the dry goods house where our mothers shopped. It is not a beautiful building. High and square shouldered, it looks like a boarding house. But it commands a splendid view, and it has a generous air, as if it had tales to tell of the hospitality that once made it a social center.

Rev. George Shipman PaysonIn the parsonage, built in 1883—it is 10 Seaman Avenue now, then it was an apple orchard—lives the Rev. George Shipman Payson, who for long, lean decades kept the faith as the head of the little church that Samuel Thomson built. During his first thirty years there were but sixty-seven Protestant families within reach of the church; often he had to wade through mud knee high to the railroad station at Dyckman Street, and he was, he pathetically says, “ten miles from a beefsteak.”

The old Dyckman home, slant-roofed and brick-chimneyed, is in an excellent state of preservation, maintained by the city as a museum.  Dyckman House near turn of the century It is on Broadway, at 204th Street. There were two Dyckman brothers, Isaac and Michael, who came to Tubby Hook in 1825 and lived their lives there, active farmers and elders in the Presbyterian Church. The house where the second brother lived is standing too, a frame building at Broadway and Dyckman Street. The McDonald family has lived there a long time and can tell you of the days when there was not an apartment house between them and Harlem. A little further down Broadway, where Fort Washington Avenue starts to wind up the hill, is a quaint wooden residence, with smooth lawns and climbing roses, and a funny old barn almost toppling over, that was part of the William Henry Hayes estate.

The former William Henry Hayes estate after its conversion into the Abbey Inn.

The former William Henry Hayes estate after its conversion into the Abbey Inn.

But the Hayes home, up on the hill, is now the Abbey Inn and the resort of motorists.

We are now in Washington Heights.

CKG Billings home

C.K.G. Billings' luxurious estate, "Fort Tryon Hall"

Fort Tryon Hall, which C.K.G. Billings, the racing man, erected above the Hudson, south of the Abbey Inn, is new from its soaring towers to its pergola, though the ground on which it stands is rich in relics of the Revolutionary War. Right here, as a tablet in the rock says, Margaret Corbin, in the battle of November 16, 1776, took her dying husband’s place at the cannon he had served and served till she was wounded too.

Libby Castle, once home to Boss Tweed

Libby Castle, once home to Boss Tweed

Across the road from the Billings place is the Norman structure, with its narrow windows and stone towers, that is called Libby Castle, though Mr. Bolton says it shouldn’t be, for Mr. Libby was inconspicuous and lived there but a short time. Boss TweedIts claim to notice is that William M. Tweed, the Tammany boss, had it for his home when he was arrested for crooked practices and fled from there to Spain. The land on which it stands was purchased in 1846 by Lucius Chittendon, a New Orleans merchant, who got ninety-seven acres for $10,000. The only road there was a driveway along the line of 187th Street from Kingsbridge Road, but he built a house and lived there in it. Angus C. Richards bought a piece of the ground in 1855 and erected the castle, which in 1869 he sold to General Daniel Butterfield, who was acting for Tweed.

Old residents say that “Bill Tweed put through Fort Washington Avenue and the Boulevard.” Lafayette Boulevard is now part of Riverside Drive. It is true. Mr. Bolton says, that we owe those streets to the fact that Tweed wanted easy access to his home. But he didn’t long enjoy his home. It was made over to his son, who lost it by foreclosure to Alexander T. Stewart, the merchant, whom Tweed owed for the furnishings of the Metropolitan Hotel, which he tried too finance. And now Father Finn, of the Paulist fathers, has it for a school for his choirboys, who may be seen almost any day playing ball in the wide grounds.

Dr. Sweetser's homeAlmost the most remarkable house now left is the one built by a Dr. William Sweetser in 1860 just a little north of the Bennett estate. In shape it is a Greek cross, with four wings jutting out to the four points of the compass. It is a satisfactory old house, not dilapidated, but sufficiently shabby and ancient to allow one ample food for dreams.

Click here for more Inwood history.

{ 16 comments… read them below or add one }

Elizabeth Lee December 15, 2009 at 12:21 pm

Cole: I love this stuff! Any chance you would consider a walk up in the woods to try to pinpoint where some of these houses stood? I’d be first on line.
Betty Lee

Cole Thompson December 15, 2009 at 2:33 pm


I’ll bet by Spring I might figure out a way to do just that. Believe me, it has crossed my mind. A bit more research, some map overlays and a GPS device and we’re in business. Thanks for checking in. Cole

Elizabeth Lee December 16, 2009 at 8:42 am

Cole: I have poked around endlessly in the non-path areas where I think buildings might have been, and although I’ve never seen anything more than bits of brick and mortar as part of broken walls/foundations(?), I find it’s more accessible in the winter because the summer undergrowth makes it pretty impassable. I have also been bedeviled by the exact location of the H of M, because on some maps, it appears to be west of the Bolton Road which puts it lower on the slope that I had envisioned. That puppy was huge…there must be some foundation somewhere! Also there is the confusion (for me) of the names, such as the House of Rest, the Memorial Hospital, and the House of Mercy. I know there was an institution run by the Magdalen Society which I think became the Memorial or Jewish Memorial Hospital, which was always different from the H of M.
You’d think there was nothing else going on in the world, and I’m obsessing about Inwood Hill 100 years ago! Have a good holiday

Cole Thompson December 16, 2009 at 9:18 am

You and me both. You make an excellent point about the winter being the best time to explore for ruins. I’ve tried it when the weather is warmer, but noting can been seen with all the undergrowth. Let’s explore after I’ve done a bit more research.

Kelli King December 16, 2009 at 5:07 pm

Cole and Betty!
I’m in for the hunt too!! I love your website. It has been infinitely helpful in learning about my new neighborhood! Thank you so much and feel free to add me to any mailing list you might have. I certainly appreciate your efforts. Also, there is a map in the Nature Center that might give additional specifics about the locations of the homes in the hills.

Marcia Rod December 20, 2009 at 3:48 pm

Count me in also. I have lived in the area since…… wow, it’s beed that long… I go into your website and read all the articles of the past and then I speak about in my History class at school. Add me to your website. I love it.

Nancy LaMuraglia Broyles December 9, 2010 at 8:16 pm

It has been wonderful to revisit Inwood on the Hudson. I was born in the apartment building at 150 Dyckman Street in 1922. Went to schools, PS 152, PS 52, PS 98. I was baptized at Good Shepard Church on Broadway when it was a small wooden church. They erected the huge beautiful chuch where I made my confirmation many years ago. We still went to mass at the old church which was moved to the street behind. I imagine that has been gone some time now. I moved away from Inwood in 1955 and have returned many times when I visited friends tht were still living there. I remember Sacret Heart of Mary Academy which closed down a number of years ago. Also we use to sleigh ride down what we called Snake Hill up in the park area. Also the Hamilton Tennis Courts use to make a skating rink during the winter months. I remember the Mirmar Swimming Pool, a hang out every Saturday all day. I even used to dive off the high board. It was lots of fun.

Living in Inwood those days and growing up there was like a small town. It was great and I have so many fond memories of those days. I often wonder if there are any old friends still alive and living there or wherever! If so contact me. Now I will return to reading about My Inwood.

Lelani Arris January 7, 2011 at 12:40 am

Thank you so much for this – feel like I just stumbled on a goldmine here, hope you can help me. I am trying to trace the genealogy/history of Ethel Richmond, the second wife (maybe) of John Brisben Walker, editor of Cosmopolitan during the late 1800s and very early 1900s. I have found her and the kids attributed to Mr. Walker (very long story) married to a John Ruthven living on Bolton Road in Inwood-on-Hudson in the 1900 US federal census (along with her mother Marion and father-in-law Charles E. Lee). Mother Marion Lee applied for a passport in 1901 giving her address as Inwood NY and her daughter signed it with address Bolton Road, Inwood-on-Hudson. Ethel and husband John appear again surely in Inwood in the 1905 New York Census (no address given but enumerated on the same page as the House of Mercy (which is how I came to find this page), and then in the 1910 US census Ethel has moved on (to Brooklyn) but her mother and a sister are still living on Bolton Road (presumably the same house).

What would help me is some sort of overlay of the old Bolton Road onto a current map, so I can see where it was. I tried with Google Earth and the very old map above, but didn’t get far. Why do I care? Where it was, who lived there before, and after, may help me figure out more about these people. And if I’m successful, you can add to your list of almost famous Inwood residents the second wife of John Brisben Walker and (less famous, but still), her sister Maude Richmond Fiorentino Valle, an artist better known in the west (where everyone went when they left NY).

Whitney April 8, 2011 at 11:43 pm

I enjoyed all of the information you presented. I believe that when you mention Libby Castle, it was originally built by Augustus C. Richards (rather than Angus Richards).

Cole Thompson April 9, 2011 at 7:43 pm

You are indeed correct. I have found other small errors in Eleanor Booth Simmons’ writings. Still, her many descriptions of Inwood are amazing. For anyone with the inclination, I highly recommend picking up a copy of her book “Round Manhattan’s Rim.” There is a whole section devoted to the neighborhood. The book is out of print, but you can often find a used copy on Amazon or Ebay.

Lauren and Alec Farber October 29, 2011 at 8:44 am

We were very interested in trying to piece together information of where and when things were then and are today. So interesting to see the first PS 52 and to hear of another G Dubbs HS. Alec is 10 and he loved learnign about Tubby Hook. Keep us informed of any community history events or projects that are going on.

Constance Brenner June 23, 2012 at 2:14 pm

Does anyone know of Henry Brenner, retired NYPD officer or his father, also a police officer? Henry Brenner lived in Inwood and was my grandfather. He died in 1945.

kurt Corrigan February 21, 2014 at 9:55 am

Hello my name iskurt Corrigan and I grew in Inwood at 30 Cooper Street. I recently discoverd my family (Moore) lived on 211 Street and Bolton road in 1901. There names were Hiram Morton Moore and wife Ida E. Moore.. Is there anyway to confirm what house they lived in and if there would be photo of the house.

RK9 June 26, 2014 at 6:19 pm

Does anyone have any information about a house located on 187th street between Broadway and Wadsworth Avenue? It is the old wooden house located at the west of the three houses.

Everytime I pass by that house, it attracts me to it. I sometimes go inside the parking lot just west of it and observe the house’s rear, how it was built, the bolts placed into it to keep the wood together and anything else.

It appears the bolts were placed by someone from the early 1900s. Also the idea of structuring the house the way it is comes from an “old fashioned” thinking.

Rhandy September 21, 2014 at 3:50 pm

Great website!! I’m from Queens and moved to Harlem few years ago and I’ve been swept up by the rich history of Inwood and Uptown Manhattan. I’d love to join a group scavenger hunt for old time places where mansions once stood or battles fought or natives’ land. Thanks for building this enjoyable and educational site!

John Calia January 1, 2015 at 11:17 pm

The old depot station in the above pictures is the Fort Washington depot on the Old Hudson River Railroad most likely just after 1921. Faint outline of the “little red lighthouse on it’s left side. Very rare!

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