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.

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.

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.  The 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.

Old 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.

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.”

And 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.

Half 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 seeingMr. 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.

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).

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.

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

The old Nathan Straus homestead is further along, on a noble slope overlooking the Hudson. 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.

The Inwood Hill home of dry goods magnate James Mcreery

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.

In 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.  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.

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

We are now in Washington Heights.

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

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. Its 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.

Almost 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.

We’ve seen photos documenting the splendor of old Northern Manhattan. Breath-taking mansions of a grander time, now gone except for a forgotten arch or lost driveway meandering around a city park. That these architectural wonders were photographed at all is remarkable.

But to step inside one of these homes, to see the art, the table settings, the beds in which these Captains of Industry slept….Well, for that you would need a time machine.

Luckily, a publishing fad erupted among the rich and famous near the turn of the century in which  the millionaire set  showcased their wealth in thick, expensive, leather-bound volumes printed in limited, private runs. Cornelius Vanderbilt himself commissioned a twelve volume set documenting his physical wealth. “These volumes were presented to his admiring friends at first, though I think, in later years this distinction was reserved for his enemies.” (Valentine’s Manual, 1928)

Estate of C.K.G. Billings

Such was the case with the private realm of Cornelius Kingsley Garrison Billings who in 1910 commissioned just such a book allowing a privileged few to inspect his inner sanctum.

Above slide-show of Billings’ home from privately published book.

Beginning in the 1901, the forty year old President of the People’s Gas, Light and Coke Company of Chicago retired, pulled up stakes and moved to Manhattan where he would shower New Yorkers with his eccentricity for years to come.

Indulging in yachts and, perhaps most importantly for this story, fast horses, Billings followed the recently opened Harlem River Speedway uptown and quickly fell in love with Manhattan’s northern edge.
He soon set to work on a 25,000 square foot lodge and stables, in what is now Fort Tryon Park, for entertaining guests.

In 1903, his lodge complete, Billings ordered an indoor, full-service, horseback dinner catered by the then famous Sherry’s Restaurant. By popular demand Billings relocated the dinner to Sherry’s midtown ballroom where 36 guests sat atop living, breathing, whinnying horses while waiters dressed as grooms catered to their every whim.

More at ease in Fort Tryon than his 53rd Street home, Billings had architect Guy Lowell build him a proper French-style mansion accessed by an S-shaped driveway that snaked up the bluff looking over the Hudson River.

Completed in 1907,  Billings magnificent home had all the trappings of the modern capitalist, a heated swimming pool, a two story squash court lined in maple and even a “fumed oak” bowling alley.

In 1916, Billings sold his beloved estate to John D. Rockefeller, Jr., who planned on destroying the home before donating the land to the City for the creation of Fort Tyron Park. The home was spared the wrecking ball after loud local protest. But like so many monuments to old New York, the home was leveled by a 1926 fire so great the Times reported, it “spouted fire and smoke like a volcano.”

This article on the Billings’ estate would not have been possible without the help, generosity and even encouragement of Inwood enthusiast Don Rice. The book, likely one of only a handful in existence, comes from Don’s private collection. Don, thank you again for sharing this book with me, and, now, the public.

Click here for more Inwood hstory.