There were more than 20 large estates in the Rhinebeck area. Unsurprisingly, the lineage of many run through the extended Beekman/Livingston families. Some of the sites became second generation McMansions, with later generations demolishing the first mansion and building a larger one to replace it.
This is an excerpt of a HABS map, the best one I could find so far with all the estate locations on it. (Ignore the dash lines highlighting Rokeby). A good map set showing the estates, exact location of houses, driveways, outbuilding, etc. is the 1891 F.W. Beers Dutchess Co. map. Sections 21-23. Link: Search results – “”Dutchess County” Atlas” – NYPL Digital Collections (top row, three on right) – or click on the top button to get to a consolidated map I put together. The second button is to James H. Smith’s 1882 History book of Du[t]chess Co. that provides the best contemporary (to that date) description of the estates. (What I provide below is synopsis history just so you have a general sense what the story is on each estate. Most are multi-generational and they have very long, detailed histories attached to them.)
Steen Valetje
Steen Valetje is named after the small brook that runs through the property. Originally the property was an old Dutch farm owned by the Benner family. In 1851, Laura Astor, daughter of William Backhouse Astor (living next door at Rokeby), and her husband Frankin H Delano, built a Tuscan style villa here. The property remained in the Delano family until 1967. Today, it is the area adjacent to the south of Poet’s Walk. A large structure stands on the site, but it is not clear if any of the original mansion survived. The card says Rhinebeck, but technically it’s in/near Barrytown, a hamlet of Red Hook.
June 2022 update, the estate is being sold. Here is a link to the Pok Journal article w/pictures:
Best selling author Suzy Welch selling Dutchess estate for $25M (poughkeepsiejournal.com)
Above card postmarked 1915. From photos inside, it appears the building that exists today is the same structure, just significantly modified. Below picture, which I believe is looking west (so likely front entrance), seems to be the side in the picture (note the 2 windows in the right jut that sticks out). The corner tower is gone.
Credit: Above current (2022) photos from linked Poughkeepsie Journal article.
Rokeby
Rokeby, also known as La Bergerie, (and also in Barrytown, and adjacent to Steen Valetje), was built 1811–1815 by John Armstrong Jr. and his wife, Alida Livingston (m.1789). Alida was the youngest child of Judge Robert Livingston (1718–1775) and Margaret (née Beekman) Livingston. Construction was interrupted by the War of 1812 when Armstrong Jr. (1758-1843), the owner, served as a Brigadier General, Minister to France, and later as US Secretary of War under James Madison. When the British burned Washington DC in 1814, Armstrong received much of the blame, as he had previously insisted that the British would not attack Washington and failed to properly provide for the defense of the city; he consequently retired to finish building his estate on the Hudson River in 1815. The Armstrong’s originally called their home “La Bergerie,” French for “the sheepfold,” as they were raising a large herd of Merino sheep – claimed to have been a gift from Napoleon Bonaparte.
In 1818, Armstrong’s daughter, Margaret Rebecca, married William Backhouse Astor, Sr. (1795–1875), son and main heir of John Jacob Astor. In 1836, William Astor purchased the 728-acre estate from his father-in-law for $50,000. The portion of the property containing the Mudder Kill is said to have reminded Margaret Astor of the glen in Sir Walter Scott’s epic poem, Rokeby, and she changed the estate’s name from “La Bergerie” to “Rokeby.”
In the mid-19th century William Backhouse Astor enlarged the house from 20 rooms to 48 in brick with brownstone trim, with a semi-octagonal tower on the west side, a north wing, and a third floor throughout the building. The service wing, tower and mansard roof date to 1857-1858. The house was later home to the Astor Orphans, the children of John and Margaret, both of whom died of pneumonia. They left instructions that their ten children were to be raised at Rokeby. Most of them grew up to become well known in politics or the arts. As the eldest son, John Armstrong Chanler inherited the property. By agreement of the siblings, Margaret Livingston Chanler bought their shares in the estate during the 1890s. Her grandson Richard Aldrich inherited the estate upon her death in 1963. It is currently owned by the Aldrich family. (Excerpted from wiki.) Below is an undated HABS photo.
I’m not entirely certain what this (below) 1905 postcard portrays. It says “Armstrong Residence” so my initial thought was it is an early Rokeby, but renovations were made before this date. Armstrong had at least three residences, this could be another one in Red Hook.
Ankony
Ankony was a Greek Revival style mansion built c1830 by William Bergh Kip (a sixth generation descendant of the original patentee). It was later enlarged and remodeled with the addition of a mansard roof. It was demolished in 1977, but a satellite view shows that the stone foundation may still exist. The property has been, and continues to be, an elite breeding farm for prize cattle. No cards exist of this mansion (at least that I know of). Here’s a sketch from James H. Smith’s 1882 History of Duchess County:
Ferncliff
Built by William Backhouse Astor Jr. (1829–1892, son of WB Astor Sr. and Margaret, occupants of Rokeby) and later occupied by his son John Jacab Astor IV (who died on the Titanic), and grandson, Vincent Astor. Demolished after World War II (the story goes that Vincent was upset about the taxes he had to pay on it). The Tennis House (c1902, aka the Ferncliff Casino), The Tea House (c1948, built by Vincent Astor), the gatehouse (c1879), and the barns remain on the site. Ferncliff Nursing Home was built up the hill from where where the mansion once stood (see my overlay map below). This is all private property and I have yet to seek permission to photograph.
Astor Courts (also known as Ferncliff Casino), designed and built by Stanford White for John Jacob Astor IV in 1904. It still exists as a private residence (Vincent Astor demolished the main structure and moved into this building post WWII.)
Gate house designed by Louis Augustus Ehlers. Built circa 1879 of stone and brick, second empire style; mansard roof. The domed entrance is missing today, otherwise it looks the same. The property is currently for sale (Oct 2021), asking price is $2.5m. Coincidently, the Tea House is also for sale, asking price is $7m. Go to realtor.com for details/interior views.
This illustration in James H. Smith 1882, History of Duchess County, seem to show the conservatory near the front gate (a green house still remains close to this location):
Quick overlay map comparing the 1891 map (see button above) with google satellite. The map does not appear to be drawn completely to scale or too precise. I deduced the mansion site based on curves in road. This is my best estimate not having walked the site yet or spoken to an expert. (Same note applies to Ellerslie map further below.)
Nursing home, now on Astor property. Undated, possibly 1970’s
Ellerslie
This mansion was the second one on this site. It replaced the c1814 mansion built by Maturin Livingston and his wife Margaret Lewis. The estate was purchased by William Kelly before 1841. It then sold to Levi P Morton in 1885, who rebuilt it as this structure by 1888. Morton was the Vice-President of the United States under Benjamin Harrison. The building burned to the ground in 1949 when at that time it was a cadet dormitory for the Cardinal Farley Military Academy.
Foxhollow Farm
Built by Tracy and Alice (Olin) Dows in 1910, adjacent to the Olin estate, Glenburn. The Beekman Arms in town was remodeled by the same architect, Harry T. Lindeberg, to look like the Foxhollow manor house. Today, it is held by a non-profit, Samaritan/DayTop Village, Inc., to provide help to people with substance abuse issues (it is on the market right now so who knows who’ll be there next, see 248 Fox Hollow Rd, Rhinebeck, NY 12572 – MLS# 396784 | C21 (century21.com) or 248 Fox Hollow Road, Rhinebeck, NY For Sale | Julia B. Fee Sotheby’s Realty (williampitt.com)
David Byars’ fantastic 2016 book, “Our Time at Foxhollow Farm” tells the full story if you are interested in learning more about this estate.
c1900 (before 1918) “Gate Lodge.” Significant overgrowth and ticks prevented me from getting to the exact spot. The stone bridge is gone (replaced in 1939), but the architecture of the house remains. Hopefully its condition does not deteriorate further. The road in this postcard seems to appear closer to the Landsman Kill than where it is today. (Note the sharp turn. This turn/road would line up with the driveway across the street, once the path to the c1710 Beekman Gristmill.
Wyndclyffe
Wyndcliff was constructed in 1853 in the Norman style. The mansion was built for NYC socialite Elizabeth Schermerhorn Jones (1810-1876, an Astor cousin by marriage) as a weekend and summer residence. Writer Edith Wharton was a frequent childhood visitor (and apparently really disliked it). In 1886, the mansion and land was sold to brewer Andrew Finck (1829-1890). Wyndclyffe was later known as Linden Hall or Finck Castle. The mansion passed from Andrew to his son, August, in 1901 and then to his grandson, August Jr. Theodore Finck (1883-1923) purchased Wyndcliffe from his brother’s estate in 1919. Theodore died in the mansion in 1923, and it passed to his daughter Anna Wolf Finck Rice (1879-1963). The mansion and 31.8 acres then passed to Nissan & Rebecca Hanoka and Mrs. Victoria Hazen in 1927 for $100 plus a $5,000 mortgage. In 1934, the property was awarded back to Anna Wolf Rice for $1,117.94 at foreclosure auction, and then passed through several subsequent owners from 1936 onward. The mansion was abandoned sometime around 1950. In September 2016 the house was sold for $120,000 at auction. The new buyer filed an application to demolish the remaining structure.
Below not a great matchup, but you get the idea. Image from internet. This is private property and I have not sought permission.
Wilderstein
Wilderstein was named after an Indian petroglyph on the property near the river; Widerstein meaning “wild man’s stone.” The original Italianate country home was built in 1852 for Thomas and his wife Catherine Murray Bowne. It was remodeled into an elaborate Queen Anne style mansion in 1888 by their son Robert Bowne Suckley and his wife Elizabeth Philips Montgomery. The renovated structure added a third floor, multi-gabled attic, a five story circular tower, a porte cochere (covered entrance), and a veranda. Landscape designer Calvert Vaux laid out the grounds in the American romantic style. Three generations of Suckleys would occupy Wilderstein. Today, it is a not-for-profit historical site. Surprisingly, I don’t have a single postcard on this estate, I’m not sure if any old ones were even published. I did want to include on this list, so using the Wilderstein website photo from 1917 as a placeholder.
Wildercliff
Wildercliff is another estate that didn’t seem to generate any postcards. This is a undated HABS photo. Constructed in 1799, it was the home of the Reverend Freeborn Garrettson (1752-1827), “an early circuit riding Methodist minister,” and his wife, Catherine Livingston (1752–1849), a daughter of Judge Robert and Margaret Beekman Livingston. The property was inherited by the Garrettson’s only child, Mary Rutherford Garrettson. In 1853, Mary Garrettson sold the north pasture to Thomas H. Suckley, the son of George Suckley, a friend of her father’s. Thomas Suckley then built Wilderstein. Suckley purchased Wildercliff from the executors of Mary’s will. It then passed to his son, Robert Bowne Suckley, who, however, continued to live at Wilderstein. Wildercliff remained with the Suckleys until it was sold in 1958. It is now in private hands. You can actually see this one from the road, it really hasn’t changed too much from the picture below.
Linwood
The original Linwood mansion was built by Dr. Thomas Tillotson in 1780. He was married to Margaret Livingston, sister of Catherine Garrettson who lived at nearby Wildercliff. Tillotson was an American physician and politician, having served as surgeon general of the northern army during the rev war. The property was purchased by Col. Jacob Ruppert in late nineteenth century (Ruppert owned Ruppert Brewery and the NY Yankees). He demolished the original house in 1883 and built the building pictured in this postcard. It was inherited by Jacob Ruppert’s nephew, Ruppert Schalk. The property was then transferred to the Sister’s of Saint Ursula, Archdiocese of New York, who burned down the mansion in c1970 and constructed a brick retreat house on the site.
Stein House
Conrad Stein operated breweries from 1867 to 1903. He may also have been a real estate developer. Stein had a bottling location in Manhattan (57th Street between 9th and 11th Ave.). Being right next to Ruppert’s Linwood estate, there was probably a connection. A photo of a small beer hall in Staatsburg with his beer’s sign on it is here: Conrad Stein’s pool and beer parlor, Staatsburg, N.Y. – Franklin D. Roosevelt Library – New York Heritage Digital Collections (oclc.org) It appears that this 1906 mansion still exists. The estate is sometimes referred to as “Whispering Pines.”
The Grove
Built c1795 by Major General Philip Schuyler on land given to him by is wife Sarah’s father, Jacob Rutsen. It was an important mill site for many years (Schuyler was partners with the Sands family, who lived across the street in that expansive white house). It was reacquired c1850 by Mary Regina (Morton) Miller, who was the [niece] of Major General Philip Schuyler. (When her husband, the Hon. William Starr Miller, a congressman, died, she built the Starr Institute in Rhinebeck as a memorial to him in 1862 (some say 1866). She also moved to Rhinebeck, purchasing and renovated the old homestead.) Her nephew, Dr. George Miller, Jr., inherited the property. (Dr. Miller, among many things, founded Northern Dutchess Hospital.) Dr. Miller’s daughters gave the property to Bard College in 1962 and it became a dormitory. Bard sold its interest in it in 1983 and it was converted into apartments.
A further part of this story follows the trail of another William Starr Miller, the namesake nephew of Mary’s husband. This William was George’s brother, and he was a lawyer and “industrialist” (and extremely rich). He owned houses in NYC, Newport (High Tide), and…Rhinebeck. He built the mansion called Rockledge, which is on a hillcrest off of Ackert Hook Rd (it resembles “The Breakers” in Newport.) More to come.
Note on above bridge card – another very similar card to this one (in thr MRH collection) shows what looks like the end of a waterfall behind one of the bridge arches. This one might require a little more checking. This bridge is not the one you see from Rt.308, though it is up that road just a bit.
Rockledge
William Starr Miller’s country estate in located off Ackert Hook Rd (google 44 Springwood Dr.). He was a nephew to Mary Morton Miller, a Schuyler descendant who owned the Grove (which was inherited by William’s brother George, mentioned above). He began buying up land in Rhinebeck in the 1890’s. Francis Hoppin, who was officially listed as the architect of record had recently completed Rhinebeck’s Church of the Messiah and nearby Blithewood in a much more formal hand. The finished estate known initially as “Castle Hill”, or “Castle on the Hill”, including the mansion, a working farm, elegant stables, miles of bridle paths a steeplechase course, private race track, and a cottage for William’s younger brother Horatio Ray, became the family’s principal country residence. His granddaughters inherited the estate when he died, and in 1945, it was sold, after which it housed a vegetarian resort, and after 1961 it was a novitiate for the Marist Fathers and home to Rhinebeck Country School. A more completely history can be found here: Rockledge, Rhinebeck’s Gilded Age Enigma — (schoolfieldcountryhouse.com)
Pawling Manor
Known for a long time as the Pawling Health Manor, we know it today as Belvedere. I’m not up on the history, but it was built c1900 in the neo-classical style. I have to ask, what the heck is going on with the blue columns? (painted as of this writing)! Mr. Hastings would likely not approve of what’s become of his old place!
Grasmere
One of the earlier major Rhinebeck estates, built by General Richard Montgomery and his wife Janet. (Janet was the daughter of Margaret Beekman and Judge Robert Livingston. To see the whole connection, see my Beekman/Livingston family tree here.) Richard died in the Battle of Quebec in Dec 1775, so he never saw the completed structure. The present day mansion (in the picture) is actually the second structure on this site. The original Grasmere burned down in 1828. There is a long history to this site (and note, the wiki history is slightly inaccurate); but in my lifetime, the estate has never been kept up. Lack of a river view didn’t help. (Janet actually moved from here in 1805 to a new mansion she built just north of Rhinebeck called Montgomery Place. It has river views and a waterfall.) This is private property, I have yet to ask for permission to enter. Photo from internet used as a placeholder.
Below card is postmarked 1906, it shows the smaller of the two barns which is now a wedding venue.
No cards, but to be updated: Leocote, Orlot, Glenburn
Staatsburg Area
Below is marked “Morgan Residence.” Undated.
The Locusts (or Locust-on-Hudson, Staatsburg Area)
Below, “Densmore’s” [or Dinsmore], long ago was the site of a Livingston mansion (that of Henry Brockholst Livingston). It was bought and sold several times until purchased by William Brown Dinsmore in 1854. He built this mansion in 1873. His Daughter, Helen Dinsmore Huntington, inherited the property and demolished the old mansion to build her own in 1941. (See wiki picture below of this one. Helen btw was married to Vincent Astor for 26 years before they got divorced.) After she passed away, it was sold to private investors. Bob Guccione, publisher of Penthouse Magazine, owned it until it was foreclosed upon in 2004. Wiki noted in 2004 it was bought by hotelier André Balazs and Uma Thurman. This mansion is adjacent to the Odgen Mills mansion in Staatsburg (on its north side).
The whole area of mansions, from Germantown to Staatsburg, was uniquely listed in 1979 in the National Register of Historic Places under “Hudson River Heritage Historic District” (https://catalog.archives.gov/id/75315704) and there was a 1973 HABS Survey done of the 16 mile area, see “Rhinebeck Area Historic Survey” https://www.loc.gov/pictures/collection/hh/item/ny0187/ (which unfortunately is not digitized.)