Category Archives: Places

Osceola Lenox Gilded Age Cottage

In 1889 Edward Livingston and his wife Sarah Pollack Livingston hired revered architect George Thomas Tilden (1845-1919)  to build their beautiful Cliffwood Street mansion – Osceola. (some sources report the build date as 1909).

It’s named for Osceola Mountain – one of the peaks of Yokun Ridge which would have been visible in the treeless days of the late 19th century.

Osceola Tour of Restored Interior

The current owners have restored the inside and outside to it’s glory including a new grey and cream paint job, restored plaster and wood exterior detail.  Ventfort Hall’s Cornelia Gilder recently gave a talk on Osceola and we were able to also see the beautifully restored interior.

















The house is described as Beaux Art, Renaissance with Colonial Revival details.

It is one of four houses in Lenox built by Rotch and Tilden.

151 Walker St., Thistelwood 1888
2 Kemble St., Frederick T. Frelinghuysen House – 1881
104 Walker St., Ventfort Hall 1893










Interestingly the second Mrs. George Morgan (Ventfort Hall) was Mrs. Livingston’s aunt. Skilled restorers Steve Baum and Jeffrey Gulick studied these Rotch and Tilden houses as well as others for clues on restoration of moldings and carpentry detail.

The Livingston’s Gilded Age Life

It’s hard to imagine a more typical gilded age couple.  Here they are in 1921 (passport photos):







Edward Livingston was part of the Livingston family that started life in America in 1686 with 160,000 acres in New York and New Jersey.

Married in 1882, Sarah Pollack Livingston also came from wealth.  Her father was a major Pittsfield textile manufacturer.  Their estate in Pittsfield, Grey Towers, encompassed acres of profitably subdivided land around Elm Street.

The Livingston family home on the Hudson had been rebuilt during the Revolutionary War and may have been one of the many places the peripatetic Livingston’s visited.

Clermont 18th Century Home of the Livingston’s on the Hudson






During the years they owned Osceola (1889-1921) the Livingston’s spent a good deal of time renting estates in England in hunt country and in Pau, France.  In the Pyrenees, Pau was a Gilded Age rendezvous for fresh air, scenery and sports.

Not the Livingston’s Home But a Typical Pau Luxury residence







For much of the time they owned Osceola it was rented to other well known Lenox families including David Dana (who later purchased what is now known as the Birchwood Inn).  The Livingston’s  had limited involvement with Lenox social life and sold Osceola in 1921 to Ellen Barker, the widow of Albert Smith Barker.  (Other sources say sold to Mrs. Dwight Collier).

Osceola in Recent Times

By 1966, Osceola had become a retreat house for General Electric.  After passing through several other owners, the house was used as a bed and breakfast starting in 1986.  The current owners have turned it back into a beautiful private residence.






Cozy Nook West Street Lenox

Cozy Nook 1900?
Cozy Nook 1900?








With many thanks to Cornelia Gilder for this wonderful write up of 17 West Street.

Cozy Nook Built Civil War Era

With its tall proportions, pitched roofs, dormers, gables and multifarious porches, “Cozy Nook” appears to be a “summer cottage” of the 1880s, but actually immured with in it, is a substantial Civil War era house. This year-round dwelling was built in 1862 by the Tuckers, one of Lenox’s leading families associated with the County government. The Berkshire County Court, housed in magnificent federal-style building on Main Street (the Lenox Library), dominated the economic and social structure of Lenox for the first seventy years of the nineteenth century.

Tucker Family Moved from House Built Over the Ore Mines

The house, which would become known as Cozy Nook, was built in 1862 by Berkshire County Treasurer and Registrar of Deeds George J. Tucker (1804-1878) and his second wife Harriet Sill Tucker. The Tuckers previously lived on Main Street opposite the Lenox Academy. That house in November 1862 (while the West Street house was under construction) was undermined by the iron mine tunneled beneath it. George’s lawyer son, Joseph Tucker (1832-1907), came home from Camp Briggs in Pittsfield where he was training with the 49thRegiment, and found the house “sunken down to the second story windows.”  (His half-brother, George H. Tucker recounted this in A History of Lenox p. G-4).

The George and Harriet Tucker apparently moved to Pittsfield with the County Court around 1871 and for awhile rented the Lenox house. (Among their tenants was Adelia Taintor (1804-1881) of Hartford a cousin of Adele Kneeland who lived across West Street at Fairlawn.)  Then in the second half of the 1870s the family house became known as “Judge Tucker’s House” after Joseph Tucker’s marriage in 1876 to Elizabeth Bishop. The bride, daughter of Judge Henry Bishop and Sarah Bishop, was a lifelong Lenox friend and had been taking care of her elderly mother in the house next door (now site of Paula Almgren’s office). The 44-year-old groom was a Civil War hero having lost his leg in Louisiana in the Union victory at Plains Store. After the war, he went into State politics and in 1873 was appointed judge of the District Court in Pittsfield.

Cozy Nook Robbery in 1878

The Gleanerreported a nighttime burglary at Judge Tucker’s house on May 15, 1878. First drugging the dog and then climbing through the kitchen windows, the robbers “knew exactly where to go and where not to go” and made off with nearly all the Tuckers’ silver and “other smaller things.”

A quiet, evening wedding occurred in the Tuckers’ house in August 1879.  Elizabeth Tucker’s orphaned niece, Lucy Pike, who had grown up as Elizabeth’s little sister was married to schoolteacher Harlan H. Ballard in the rooms of the house. Six months later Elizabeth Tucker died. Bereft, Judge Tucker sold the Lenox house in 1882 and moved nearer the Court in Pittsfield, but he remained active in Lenox. He appears in an 1886 photo of men posed on the porch of the Lenox Club.

Old Lenox Club Walker Street
Gentlemen on the Porch of the Old Lenox Club






Helen Parish New Owner

The new owner, a New York heiress of a dry-goods business, Helen Parish (1843-1925) transformed the twenty-year-old Judge Tucker house to its current stately appearance. She named the place “Cozy Nook” and summered here until her death 43 years later.

She was the twelfth and youngest child of Daniel and Mary Ann Parish and bought the house two years after her father’s death. In January 1883 The Lenox Echoreported “ The George Tucker estate recently purchased by Miss Parish will be scarcely recognizable when the house and grounds are finished.” Indoor plumbing was installed, as well as fine woodwork with classical motifs.

Supporter of Library and Lenox Band

Helen Parish was a supporter of two nearby institutions, Lenox Library where she served on the Assistant Board of Managers, and the Lenox Band, which held summertime concerts in front of the Curtis Hotel within earshot of Cosy Nook’s porches.

Lenox Band in Front of Peter's Bike Shop
Lenox Band in Front of Peter’s Bike Shop







After Helen Parish’s death in 1925, her neighbor George Turnure purchased the house for his recently divorced daughter, Irene Kissel. In 1940 Norah Codman (1873-1961) bought Cozy Nook with her brother Frederick Chadwick. She was a longtime frequenter of Lenox and widow of lawyer Julian Codman (a glamorous literary and social figure in his Harvard years in the circle of George Santyana, and later during Prohibition of the 1920s, a leading opponent or so-called “Wet”).  After selling Cozy Nook, Norah Codman lived on in Lenox, renting rooms at “Heathercroft” on Walker Street, (next to today’s Talbots).

Became Home of Author Robert Smith

In 1945 author Robert Smith bought Cozy Nook, and for the next sixty years his family lived in the imposing Victorian house. Here Smith wrote some six novels and many books in collaboration with sports and military heros. His best known work, entitled Baseball,was published by Simon and Schuster in 1947. When the book first came out, editor Norman Cousins began his lengthy review inSaturday Review, “I dare anyone to meet me under the grandstand who says this isn’t the best book on baseball ever published.”

Ninety-one year old Smith died on a fishing trip in Maine in 1997. His second wife, Jean Kelly Smith (1923-2016), who married Smith in 1955, made Cozy Nook her home for half a century.


  1. B. Gilder 2017


Lenox as a Resort – Main Street

Screen Shot 2016-02-04 at 1.22.00 PM
Cornell Inn as of 2016 – 203 Mian

Screen Shot 2016-01-28 at 4.17.57 PM Screen Shot 2016-01-28 at 4.19.41 PMMacDonald Farm/ Twin Maples/ Cornell Inn

The Cornell house was built in 1888 by the Cornell family, having purchased the property from the MacDonalds, next door. For most of its existence the Cornell Inn has been a lodge, an inn, a bed & breakfast or a way house for weary travelers on the road from Albany to Boston. Eventually, when the last of the MacDonald family passed on, leaving no kin, the then-owners of The Cornell Inn purchased the MacDonald house (built in 1777) adding it to the inn.




The Aspinwall

Aspinall Hotel - 1902-1931
Aspinall Hotel – 1902-1931

In 1902 General Thomas H Hubbard built the elegant Aspinwall Hotel in what is now Kennedy Park (Woolsey Woods).  It had

Aspinall Guest House
Aspinall Guest House

spectacular views, luxurious rooms, guest houses, trails and important guests.  It burned suddenly in 1931.




Hillside/ Kuhn Harman House/The Hidden House/ Whistler’s Inn

Hidden House - 1870
Hidden House – 1870

Hillside was built by Mrs. Hartman (Grace) Kuhn of Boston in 1870, and used by her during the ‘season’.

Mrs. Hartman Kuhn (Grace Morris Cary)
Mrs. Hartman Kuhn (Grace Morris Cary)

Mrs. Kuhn, who also purchased Butternut Cottage, owned the entire lot along Main St. from Greenwood to the Kingsland House (at the junction of Main and Cliffwood Streets). By 1890 the house was being rented

5 Greenwood St., Hartman Kuhn House - 1870
5 Greenwood St., Hartman Kuhn House as It Appeared in 2014

to Mrs. Cruger of New York, and around 1911 it was sold to Mr. and Mrs. Ross Whistler, who renamed it Hidden House. Mr. Whistler, who had made his fortune in railroads, was a nephew of the famous painter and brother of Joseph of Plumstead on Old Stockbridge Road.










Israel Dewey House/ Hubbard Tavern/ Dana Summer Home/ Birchwood Inn

Birchwood as It May Have Looked When the Dana's Summer Home - 1880's
Birchwood as It May Have Looked When the Dana’s Summer Home – 1880’s

The original portion of the structure (corner of Hubbard and Main) was the home of Israel Dewey, one of Lenox’s earliest settlers. Dewey, who established a home in the area by 1764, was one of the proprietors of Lenox and served in a number of public positions. Like many Berkshire householders, Dewey was licensed as an innkeeper. He left Lenox for Vermont in the early 1790’s, and after several changes in ownership the property was acquired by Zadock Hubbard in 1798. He enlarged the house and opened it as the Hubbard Tavern. In 1806 the building was sold to Azariah Egleston, a locally prominent man, and converted back to a private residence. The house was substantially enlarged and altered after Mary Loring bought it in 1868. In 1885 it was sold to Mr. and Mrs. Richard S. Dana of New York and was remodeled for use as a summer home.  Currently it is operated as Birchwood Inn.

Eliza Williams House/ Butternut Cottage/ Garden Gables

Butternut Cottage - Kat Carey Era -
Butternut Cottage – Pre Kate Carey Era – c. 1861

The original portion of this house was built by Susan and Eliza Williams on the site now occupied by 101 Main Street. Eliza Williams lived here until 1873 when the house was purchased by Mrs. Kuhn who had built “Hillside” around 1870. Eliza Williams may have continued to live in the house as a tenant,

Kate Carey - Horsewoman and Philanthropist
Kate Carey – Horsewoman and Philanthropist

as she is listed in the 1885 directory as having a house and lot on Main Street.

In 1905, the house was sold to Caroline Katherine Carey (Miss Kate Carey), who moved the front portion of the house to its present location, adding on an extensive wing containing servants’ quarters and a storeroom, and apparently remodeling the entire

135 Main St., Eliza Williams House - c. 1861
135 Main St., Former Eliza Williams House Now Garden Gables

house. Miss Carey used part of the first floor servants’ wing as a carpentry shop, where she built doll and bird houses. Upon her death in 1945, the property was deeded to Trinity Church, who in turn sold it to Joseph Reynolds. In 1951, it was sold again,  renamed Garden Gables and opened it as an Inn and gift shop.

The Congregational Parsonage

136 Main St., Congregational Church Parsonage
136 Main St., Congregational Church Parsonage – c. 1895

This charming Queen Anne style home stands on the site of the original Congregational parsonage, a brick building dating from 1852. By the 1890’s it had fallen into disrepair and the congregation elected to build a new house on the same site.  It is included in this description of Lenox as a Gilded Age resort only because it reflects the way the prosperity of the time spread out to effect the lifestyle of even the humble Congregational minister.  According to a turn-of-the-century magazine article, “Few Congregational Churches in Massachusetts have so fine a home for their ministers”.

This house was used as a parsonage until 1925, when the Congregational Church was given the Worthington House on Cliffwood Street which became the home of the minister.

Sunnyholm/ Sunnyhome

33 Main St., Andrew Thompson House - c. 1870
33 Main St., Andrew Thompson House – c. 1870

Andrew Thompson purchased this lot in 1836, and built this house. In 1850 Horatio Sears purchased the property and resided in the house until his death in 1861.  It changed hands several times.  When it was purchased in 1872 by Andrew and Harriet Servin it was completely remodeled.   Around 1900 it was purchased by B.K. Stevens, who named in Sunnyhome (also “Sunnyholm”).   It has been, most recently, a therapeutic facility.

The Lanai

17 Main St., Electa Eddy House - c. 1883
17 Main St., Electa Eddy House/The Lanai – c. 1883

This house was built on the site of an earlier house demolished in the late 1870’s. The lot was purchased from the owner of that house, Lucy Cottrell by Electa Eddy in 1880. In 1886, it was sold to John Egmont

J.E. Schermerhorn Home
J.E. Schermerhorn Home

Schermerhorn. Mr. Schermerhorn named the house “The Lanai”, perhaps referring to its original porches.    It is currently operated as the White House Inn.


The Curtis

The original temple front structure, which forms the core of the present building, was probably designed as a counterpart to the Second County Courthouse of 1816 (now the Lenox Library).

This corner has been the sight of an inn of some sort since at least 1773 when the tavern standing here served as a stop on the stagecoach route from Hudson, N.Y. to Pittsfield. Traffic in the town increased after Lenox was made the county seat in 1784.

From about 1793 the Berkshire Coffee House operated on this site, and became famous as the gathering spot for people conducting business at the county Courthouse (then located across the street on the present site of Town Hall).

1839 Print Showing the Red Inn (Curtis) Before the Mid-Century Additions
1839 Print Showing the Red Inn (Curtis) Before the Mid-Century Additions

In 1829 a brick hotel was built by Peck and Phelps, “at the urgent request and demand of persons attending the courts for increased and sufficient accommodations.”  For short time iw was rented to George W. Platner, and was then purchased by major S. Wilson. According to one mid-century guidebook “ the principal hotel – so situated as to command a favorable view, both of the village and distant scenery – has become, under the care of its efficient proprietor, M.S. Wilson, Esq., a favorite resort for visitors from the cities.”

William Curtis and the Mid-Century Hotel
William Curtis and the Mid-Century Hotel
View Showing the Late 19th Century Addition
View Showing the Late 19th Century Addition

The hotel was purchased by William O.Curtis in 1853, and has been known as the Curtis Hotel ever since. The Curtis family was responsible for much of the hotel’s ensuing success, and William O. Curtis and his son, William D. Curtis, were active members of the community. The loss of the County Court in 1868 had little impact on business at the Curtis, which by this time was catering to a growing number of seasonal visitors. Beginning in the mid-nineteenth century, and accelerating rapidly after the Civil War, a stream of visitors came from New York, Boston, and other cities to experience the healthful climate, take in the views from its veranda, and join in the social activities that took place there.

Reception Area - Curtis Hotel c. 1900
Reception Area – Curtis Hotel c. 1900

Many guests returned year after year: some, desiring more space and privacy than the hotel rooms afforded, rented houses on Main and Walker Streets, also owned by the Curtis’s. These became known as “Curtis Cottages” and their occupants as “cottagers”; this has been cited as the origin of the term “cottagers” to describe wealthy summer residents in Berkshire. By the final decade of the 19th Century the Curtis served as overflow housing for owners of large estates, or was used by the estate-owners themselves before and after the “season” when their homes were not fully staffed. The building was greatly enlarged in 1883 and again in 1898 to accommodate these patrons.

6 Main St., Curtis Hotel as It Looked in 2014
6 Main St., Curtis Hotel as It Looked in 2014

The Curtis family continued to operate the hotel through the 1930’s, but he decline of summer visitors to Lenox (brought about by the institution of the income tax and the stock market crash of 1929, which made the upkeep of a large estate nearly impossible; and the Depression of the 1930’s which restricted the traveling of most Americans) made the business difficult to keep up, and the building was sold after World War II. Although subsequent owners kept it operational as a marginally successful hotel, the building suffered from some neglect and deterioration. After failed attempts to revitalize the hotel by new owners in 1970 and 1976, the town of Lenox acquired the building in 1979 and converted it to use as housing for the elderly, with retail space on the first floor.

Celebrity guests included US President Chester Arthur, abolitionist Rev. Henry Ward Beecher, Sen. Charles Sumner, Gens. George McClellan & William T. Sherman, Newspaper Editor Horace Greeley, Kentucky politician Cassius M. Clay, Robber Baron “Big Jim” Fiske, business magnate John Jacob Astor, poet James Russell Lowell and Curtis’s longtime friend, British actress Frances Ann “Fanny” Kemble, who nicknamed the hotel “The Old Red Hen.”  Writers Nathaniel Hawthorne (1804-1864) and Herman Melville (1819-1891) said to have dined together in Curtis Hotel dining room, Nov 1851, possibly exchanging advance copies of their latest books, The Wonder Book and Moby Dick respectively

Lenox as a Resort – Cottages to the North


Fernbrook - 1904
Fernbrook – 1904

Fernbrook was constructed in 1904 for Thomas Shields and Adelaide Knox Clarke. On West Mountain Road it stands today as Hillcrest School.





Valleyhead - 1902
Valleyhead – 1902

Valleyhead was built in 1902 for J. Frederick Schenck and Mary Louisa Stone Schenck.  It is described as adjoining Home Farm so must have been on   Reservoir Road above Undermountain Road.  After it passed out of the family it was a therapeutic facility for awhile.  It burned in 1987.

Home Farm

Home Farm - 1902
Home Farm – 1902

Rounding the curve from Cliffwood to Undermountain, there is a beautiful vista across Undermountain Farm.  Home Farm looks out over that vista.

George C. Harding built this home for Dr. Henry P. and Caroline Ware Jaques in 1902. It has also been known as Waterford and Highjack Farm.

It was described in David Woods’ Lenox Massachusetts Shire Town (1969) as adjoining the golf course.  Something has changed in the terrain since then.

It is still a private home.

Undermountain Farm, across the street, was built, in the 1870’s,  by Henri Braem (Stonover) as a model farm.

Pine Needles

Pine Needles - 1903
Pine Needles – 1903

Hidden deep in the forest off Undermountain Road,  Pine Needles was built by Winslow and Bigelow for George Baty Blake (1871-1928) and Margaret Hunnewell Blake (1878 – 1967).  Landscape architects Brett and Hall of Brookline laid out the curving driveway as well as the sit of the stable and walls.

To attend to George’s tuberculosis, the couple lived in the house year round.  The home is still privately owned.

Woodcliff – Gone But Not Forgotten

Woodcliff - 1854
Woodcliff – 1854

When William Aspinall built his gothic, porched house on a hill above Church on the Hill, it was out of the mold of the Wards, Sedgwicks, etc.  First, he was from New York (the Pacific Steamship Company) and second he built on a scenic but distant spot.  He arrived in town

Early Photo of the View From Woodcliff
Early Photo of the View From Woodcliff

with a retinue of six coachmen, 21 horses and an army of servants.  The large parties of guests often included Edward J. Woolsey who was married to William’s sister Emily.  William’s brother John was a business partner.  Between 1853 and 1860, the family accumulated 500 acres of the ridge.  In a preview of things to come as Kennedy Park, the Aspinwalls and Woolseys allowed townspeople to wander through the scenic woods.

The house faced north – looking at Mount Greylock; the opposite of the Aspinall Hotel which was to follow in the 20th century – facing the southern view over Parson’s Marsh.

The house is no longer standing.

The Dormers

The Dormers - c. 1868
The Dormers – c. 1868

Richard T. Auchmuty was a Civil War veteran and an architect.  In addition to designing his home in Lenox, The Dormers, he would become active in the

Richard Auchmuty
Richard Auchmuty
Ellen Schermerhorn
Ellen Schermerhorn

construction of the new Trinity Church.  His wife, Ellen Schermerhorn, daughter of the widow Caroline Schermerhorn had grown up at Pinecroft in Lenox.

The Dormers still stands above Route 20 north of town and is part of the Twelve Oaks condominium development.


For much more on the architecture of these houses and the people who lived in them, see

Houses of the Berkshires, 1870-1930, by Richard S. Jackson Jr. and Cornelia Brooke Gilder, Acanthus Press, 2006

The Tanglewood Circle, Hawthorne’s Lenox, by Cornelia Brooke Gilder with Julia Conklin Peters

The Berkshire Cottages, A Vanishing Era, by Carole Owens, Cottage Press, Inc. 1980


Lenox as a Resort – Hawthorne Street

Many of the historic houses of Hawthorne Street are actually in Stockbridge – but they’re often associated with Lenox.

Hawthorne Street as we know it did not exist at the time of some of the early estates discussed, so we’ll have to use some imagination as to location.


Highwood (Much Altered Since the 1844-1845 Original
Highwood (Much Altered Since the 1846  Original)

When the Wards of Boston constructed Highwood, they touched off the era of Lenox as a resort.   Intellectually curious and engaging, they attracted others to the lovely setting.

Highwood is now owned by the Boston Symphony Orchestra and is used for Tanglewood special events.


Tanglewood - c. 1865
Tanglewood – c. 1865

Tanglewood was built by Caroline Sturgis Tappan (1819-1888) overlooking the Stockbridge Bowl.   Caroline and her husband, William Aspinall Tappan (1820-1905) had purchased the property in 1849 next door to their friends the Wards.  Until they built their own

Recreation of Hawthorne Cottage (Original Burned in 1890)
Recreation of Hawthorne Cottage (Original Burned in 1890)

property, they stayed at the red cottage that would be home to the Hawthornes in 1850 and then rented Highwood from the Wards.

Given the highly cultural bent of this family, it’s not surprising that Caroline’s granddaughter, Rosamond Dixey Brooks, offered Serge Koussevitsky the family house, gardens, lawns and farm as a home for the summer music festival.


Wheatleigh - 1893
Wheatleigh – 1893

Wheatleigh was initially built for railroad financier H.H. Cook, who may have intended the property for one of his daughters from the start.  He gave Wheatleigh to his daughter Georgie who had married Signor Carlos Manuel d Heredia. The groom was originally from Cuba and was sometimes called the Count de Heredia. Wheatleigh

Woody Guthrie and Pete Seeger at the Lenox Jazz Festival
Woody Guthrie and Pete Seeger at the Lenox Jazz Festival

and been designed by Peabody and Stearns with plans for the ground by Frederick Law Olmsted.

Mrs. De Herdia’s husband died in 1918 but she continued to spend part of her year at Wheatleigh, until her death in 1946.

The main house survives as a luxury hotel, but the rest of the estate was broken up and took different directions. Some of the outbuildings were used in the 1950’s and 1970’s for the Lenox Jazz festival which brought a lot of new rhythm and folk music to the

Music Inn
Music Inn

Berkshires. The next step in the evolution of music in the area was Music Inn which drew crowds with acts ranging from Joan Baez to the Kinks.

The outbuildings have now been repurposed as White Pines Condominiums.


Brookhurst 1 -
Brookhurst 1

The couple that built (the second) Brookhurst exemplified how closely associated the cottagers were – in Lenox and elsewhere. The husband in the couple, Newbold Morris (1868-1928) was Edith Wharton’s cousin and used many of the same designers that Mrs. Wharton had used on The Mount: Ogden Codman and Beatrix Jones (Farrand).

Caretaker Cottage - May be Left From Original Brookhurst Estate
Caretaker Cottage – May be Left From Original Brookhurst Estate

The original Eastlake style Brookhurst (except for the stable and gatehouse) had burned. That gave the couple a free hand in building a new house and they hired Francis Hoppin to design a very different looking Georgian revival house.

The Morris Family

Brookhurst II - 1908
Brookhurst II – 1908

Newbold’s family had roots back to colonial New York and New Jersey. His wife, Helen Schermerhorn Kingsland Morris (1876-1956) was a second cousin with equally deep New York connections.

George and Suzy's Modernist Home on Brookhurst Grounds
George and Suzy’s Modernist Home on Brookhurst Grounds

Of the three sons, one, George Morris, built his now famous modernist home and studio on the property with his wife, the former Suzy Frelinghuysen. It is now a museum open to the public.

Some of the land on the estate was donated to the Town of Lenox for the Morris Elementary School on West. St. As an added gift, George

Morris Elementary with Mural
Morris Elementary with Mural

Morris painted an abstract mural which stands at the school entrance today.

Another brother, Stephen, took over the main house, but had it reduced in size. That house has now been sold out of the family but remains in private hands.


For much more on the architecture of these houses and the people who lived in them, see

Houses of the Berkshires, 1870-1930, by Richard S. Jackson Jr. and Cornelia Brooke Gilder, Acanthus Press, 2006

The Tanglewood Circle, Hawthorne’s Lenox, by Cornelia Brooke Gilder with Julia Conklin Peters

The Berkshire Cottages, A Vanishing Era, by Carole Owens, Cottage Press, Inc. 1980


Lenox as a Resort – West Street Cottages

Judge Bishop House – Gone But Not Forgotten

Judge Bishop House
Judge Bishop House

Corner of West and Main.







Cozynook – 1865

Cozynook was built for George Tucker in 1865.  This charming house would have been less a “cottage” than just a very nice, mid century home.  It stands today and is apartments.

There were multiple generations of Tuckers – each generation containing at least one attorney working on county and town business.   One of the most recent, and most appreciated, public service was that of a recent George Tucker who wrote an unpublished manuscript that is a reference for local historians. (see Lenox Library or Lenox Historical Society).

Nestledown – Gone but Not Forgotten

Nestledown - 1867
Nestledown – 1867

Alice Sturgis Hooper (1841-1879) was the daughter of Boston based Congressman and shipping magnate, Samuel Hooper.   When she built the house that would be called Nestledown, she  used a fanciful stick style similar to that used for Dr. Greenleaf’s Windyside so they might have had the same architect.

It is described as being on the site of the former gallows on the steep part of West Street. That would place it someplace between the Paterson Monument and Kneeland.  She was active in cataloging the Lenox Library.  She died (tuberculosis?) in 1879.

Summerwood/ Fairlawn

Fairlawn - 1870's
Fairlawn – 1870’s (Lenox Library)

A home called Summerwood was built on this site (where Kneeland Ave. currently intersects West St.) for Sarah Starr Lee about 1847.  Lenox born Sarah’s grandfather, Joseph Goodwin, had been a partner in the early iron works. Hawthorne’s Lenox includes colorful stories of the wealthy widow’s life at Summerwood.

In the 1870’s the property was acquired by the Kneeland family.  They would transform both the house and grounds

With the death of her father and grandfather, the unmarried daughter, Adele,  was a wealthy heiress by the 1880’s.  She had (what gilded age family would be

Fairlawn Gardens
Fairlawn Gardens
Adele Kneeland (?)
Adele Kneeland (?)

complete without one) a strict aunt who disapproved of George Haven Jr. who she loved.  So Adele remained single and poured her energy into Trinity Church and a magnificent garden at this site.  In addition she had Ogden Codman do the decorating – so the house must have been lovely inside and out.

The site was in place until at least 1937 when Adele died.

Sketch of Fairlawn Grounds
Sketch of Fairlawn Grounds

Her nephews eventually had it demolished and the site was broken up into lots that now contain the housing along Kneeland Avenue.

The extent of the gardens is shown on this drawing.  It must have been a beautiful site walking down West Street.



Cushman Cottage?

Per David Woods appendix:  built 1860 by Mrs. F. R.. Beck, bought by Charlotte Cushman in 1875.  She died soon after and it was sold to Emma Stebbins.  Demolished; where Brunel Ave. housing is currently.

The Elms/ Groton Place

The Elms - 1858
The Elms – 1858

Although there was no Yokun Avenue until the 1870’s, The Elms was across from where Yokun would be as early as 1858.  The 1858 version was built for William Ellery Sedgwick and

Grenville Winthrop
Grenville Winthrop

wintrop-house-groton-place-CF46568831_120278530120Constance Irving Brevoort Sedgwick.  Ellery was the nephew of Charles Sedgwick of “The Hive” and the Lenox county courts.  This seemingly “golden” couple fell out of domestic bliss* and the house was sold in 1871.  Subsequent owners did a good deal of re-building until the property was sold in 1902 to Grenville Winthrop.

Grenville, who later some colorful domestic issues of his own*, changed the name to Groton Place, expanded the house, purchased additional property and invested in major landscaping.

Beginning in 1946, Groton Place became the home of the Windsor Mountain School.  It is currently the home of the Berkshire University Tanglewood Institute.

Shadow Brook/ Oakwood

Kripalu Yoga Retreat
Kripalu Yoga Retreat

This highly visible and scenic site (across from Tanglewood) is now Kripalu Yoga Retreat.  It was built for the Jesuit Society to replace Shadow Brook

Shadow Brook Burned 1956
Shadow Brook Burned 1956

which burned to the ground in 1956.   It had been gifted to the Jesuits in 1922 after one of its many illustrious residents, Andrew Carnegie, died there in 1919.  Itwas built in 1893 by Anson Phelps Stokes and, at 250 rooms was, for awhile, the largest house in America.

Oakwood, 1876
Oakwood, 1876

Shadow Brook did not replace Oakwood as much as consume it.

Oakwood had been built by Charles McKim for Samuel and Anna Ward, who had originally built and owned nearby HIghwood in 1844 – essentially kicking off Lenox as a resort community. The Wards sold the property to Anson Phelps Stokes in 1891.  Stokes used it as a stable and it burned to the ground in 1903.

The Corners/ Maakenac Farm/ Higginson’s Farm

Mahkeenac Farm - 1886
Mahkeenac Farm – 1886

In 1860 George Higginson, Jr. (1832-1921) purchased the Wilcox Farm next to what would have been the Tappans’ place (now Tanglewood).  His purchase included 150 acres and a view of what is known today as Gould Meadows and an old farmhouse.  George’s family was friendly with the Wards (Highwood) and Oliver Wendall Holmes and he had been a frequent Lenox visitor.  After started a career (with his uncle Henry Lee and William Bullard) in the East India trade, George decided to commit to the life of a gentleman farmer and proceeded to study “practical farming” and set up a model farm.  By 1862 he had transformed the old farmhouse and brought home his bride, Lili Barker Higginson (1836-1901).

The Pines/ Lakeside

Lakeside - 1894
Lakeside – 1894 (Lenox Library)

This attractive site was originally a farmhouse called The Pines owned by Juliette Starr and Richard Perkins Dana.  They sold the property to Charles Bristled Sr. in 1864.  The original farmhouse on the property burned in 1885.

The Colonial Revival home that stands today was built for Charles Bristed’s  son, also Charles Astor Bristled,  by Pittsfield architect H. Neill Wilson of Pittsfield  The architect had also designed the mammoth Shadowbrook next door.

The younger Charles practiced law for a few years but was primarily living on his considerable Astor fortune.  Over time, he expanded his Stockbridge landholdings to over 400 acres.  Even that wealth thinned out after Charles’ death in 1936.  His daughters continued to stay at Lakeside and the property remains in family hands.

Beckwithsaw/ Bonnie Brier

Mark Hanna (1837-1904)
Screen Shot 2016-01-31 at 9.43.42 AM
Bonnie Brier (Rt. 183 Stockbridge) – 1892

Initially known as Bechwithsaw, Bonnie Brier was built by Harry Weeks and H. Neil Wilson for Mark Hanna.  Mark Hanna was the Ohio kingmaker largely responsible for making McKinley President.

Hanna assembled about 1,100 acres including 2,500 feet of frontage on the Stockbridge Bowl.  Leonard Forbes Beckwith had a “villa” on his 500 acres which was remodeled and then disassembled by Mrs, Samuel Hill of Seattle, who had also added to the acerage.   Mark Hanna used the property to raise prize stock.  It passed to his son Daniel Rhodes Hanna before taking up its history as a school.

Bonnie Brier (still standing and for sale as of this writing) has been the site of one of the first (if not the first) Berkshire Music Festivals at what was known as “Hanna’s Farm”  (think Tanglewood) in 1935 and the Stockbridge School (a progressive education school akin to Windsor Mountain School) 1948-1976.  Most recently, it was the home of the DeSisto School


For much more on the architecture of these houses and the people who lived in them, see

*Houses of the Berkshires, 1870-1930, by Richard S. Jackson Jr. and Cornelia Brooke Gilder, Acanthus Press, 2006

*The Tanglewood Circle, Hawthorne’s Lenox, by Cornelia Brooke Gilder with Julia Conklin Peters

The Berkshire Cottages, A Vanishing Era, by Carole Owens, Cottage Press, Inc. 1980

Lenox as a Resort – Cliffwood Cottages

Cliffwood  has so many lovely homes today that they could all be considered estates in modern terms.  For the sake of manageability, this enumeration is limited to those that have been written up as “cottages.”


Osceola - 1889
Osceola – 1889

Known as Osceola, 25 Cliffwood was built for Mr. and Mrs. Edward Livingston in 1889 by Rotch and Tilden.  It has been used as a retreat for General Electric  and an Inn.  It is currently a private residence.

Sunnyridge I & II

Sunny ridge - 1884
Sunnyridge – 1884

This house was built as a summer home by Mr. and Mrs. George Folsom in 1884.  AT the time it would have been next to the (also later burned) Homestead on Cliffwood St.

The half timbered house was designed by Charles Coolidge Haight.  Houses of the Berkshires* contains wonderful stories about the life and times in this book laden old house.

Mr. Folsom was the law partner to President Grover Cleveland. Miss Frances Folsom married the President in the first White House wedding. She was 22 years old and President Cleveland was 50 at the time.

Sunnyridge Replacement (49 Cliffwood) - 1925
Sunnyridge Replacement (49 Cliffwood) – 1926

In 1925 the original house was destroyed by fire and it was rebuilt the following year. Built in the English cottage style, the new house was designed by Delano and Aldrich.

The Homestead

Homestead – 1885

Completed in 1885, The Homestead was designed by Charles McKim with landscaping by Frederick Law Olmsted.  His client, Julia Amory Appleton (1859-1887) must have been pleased with his beautiful design as she married the recently divorced McKim the same day her sister married George von Lengerke Meyer.  Tragically she died two years later and McKim sold the Homestead to Anson and Helen Stokes in 1889.

Julia Amory Appleton McKim
Julia Amory Appleton McKim

They expanded the house (a lot) foreshadowing their future edifice – Shadow Brook.  In 1905, when the house was rented to the Eric Dahlgren family, it burned to the ground. Fearing a takeover by “outsiders” George Folsom, Morris Jessup, John E. Parsons and Grenville Winthrop bought the site.  The Homestead was replaced in 1914 and 1915 by 57 and 61 Cliffwood Street, designed by Harding & Seaver.

71 Cliffwood
71 Cliffwood

Although the numbers do not match the Harding and Seaver home shown here is described as being on one of the lots formerly occupied by The Homestead.


Breezy Corners

35 Greenwood Street
35 Greenwood Street

This Greenwood Street property primarily fronts on Cliffwood.   As an 1870’s farmhouse expanded over the years, it is more typical of earlier summer homes than the other more elaborate architectural cottages on Cliffwood.  It is most often written up because it sheltered one of America’s most prestigious families — the Biddles of Philadelphia..  Their Quaker ancestors came to Philadelphia before American Revolution and had been active in science, law and banking ever since.  Mrs. Jonathan Williams Biddle bought the property in 1886.  Her daughter, Miss Emily Biddle came there every summer until her death in 1931.  She was a founding member of the Lenox Horticultural Society and active in the Tub Parade and other Lenox activities.  The property is a private home.


Belvoir Terrace 1891
Belvoir Terrace  (80 Cliffwood St.) – 1891

Belvoir Terrace was designed by Rotch & Tilden and built between 1888-1890 for Morris K. Jesup, with landscaping by Frederick Law Olmsted.  Facing Cliffwood Street and with a “side” entrance on Greenwood Street, this highly fanciful property also had an entrance from Main Street, next to Church on the Hill.

Morris K. Jesup (1830-1908)
Morris K. Jesup (1830-1908)

Morris K. Jessup (1830-1908) was a successful banker and a notable philanthropist. His philanthropic activities included backing Robert Peary’s Arctic expedition and being president of the Museum of Natural History.  He was, along with several other super wealthy Lenox cottagers, in the Georgia Jekyll Island Club.

Belvoir is currently an arts and music camp. It is easily visible from Cliffwood Street.


Screen Shot 2016-01-29 at 9.08.19 PM
Underledge – 1889

Underledge, still standing as a handsome private residence, was built for Mr. and Mrs. Joseph W. Burden.

Little has been found about the Burdens other than regular references in the social columns to her teas and his golfing prowess.


Rocklawn - 1888
Rocklawn (89 Cliffwood St.)  – 1888

Once part of Windyside, this home was built for William and Elizabeth Stone Bacon.




Deepen - 1886
Deepen – 1886

Up the street from Rocklawn Francis Parker Kinnicutt and Eleanora Kissel Kinicutt built Deepened in 1886.  The final home on the tour, Deepdene, was constructed as a Colonial Revival summer cottage on Cliffwood Street in 1886. Deepdene was designed by Bruce Price, an important New York architect. The owners were the socially prominent Dr. Francis and Mrs. Eleanora Kinnicutt. Edith Wharton was one of the doctor’s patients and encouraged her to move to the Berkshires. The entrance is directly into a soaring stairhall while many porches originally overlooked the expansive green of the Lenox Club golf course.   The golf course has now been re-absorbed by the woods.


For much more on the architecture of these houses and the people who lived in them, see

*Houses of the Berkshires, 1870-1930, by Richard S. Jackson Jr. and Cornelia Brooke Gilder, Acanthus Press, 2006

The Berkshire Cottages, A Vanishing Era, by Carole Owens, Cottage Press, Inc. 1980

Lenox as a Resort – Old Stockbridge Road

Jonathan Hinsdale - First European Settler of Lenox
Jonathan Hinsdale – First European Settler of Lenox

A plaque across from Hawthorne Street celebrates the location of the first settler of Lenox – Jonathan Hinsdale.  It was, for a long time, the primary north-south route to Stockbridge and it has beautiful views.  So it is not surprising that this street was a major location for beautiful homes – in the early days up to today.  Some remain, some are gone.

Rev. Justin Field House

The Original, Modest Rectory for Trinity

Not a “cottager”from a wealth stand point,  but an important figure in Lenox’s Gilded Age era, Rev. Justin Field was a long-time (1862-1890) rector of Trinity Church and a leader in constructing the new church on Walker.

The space was also used as a boarding facility for students of Elizabeth Sedgwick’s school — including young Jenny Jerome (future mother of Winston Churchill).

20 Old Stockbridge Road as It Appears in 2016
20 Old Stockbridge Road as It Appears in 2016

In keeping with the newly robust and wealthy congregation,  the space was upgraded to the Tudor-like structure that stands today at 20 Old Stockbridge Road as a private residence.   In 1892 a new rectory was built on the Trinity Church grounds.



Miss Lippicott’s School

School or Perhaps Living Space for Lenox Academy and Other Private Schools
School or Perhaps Living Space for Lenox Academy and Other Private Schools

The building that still stands today as privately owned condominiums, was similarly, a re-work of an earlier structure and a facility for wealthy visitors.  It has also been referred to as Tanner Cottage.


Moved and Changed

Rockwood (11 Old Stockbridge Road) - c. 1880
Rockwood (11 Old Stockbridge Road) – c. 1880

One of the first buildings you encounter on Old Stockbridge Road, now the Rockwood Inn, began life elsewhere.  It was known as the Williams Tavern in 1825 and was located where Main and Cliffwood now meet.  It would have been one of many taverns that did a land office business during Lenox’s busy court days.

Leonard Constance Peters
Leonard Constance Peters

Around 1880, the building was purchased by Leonard Constance Peters who started a number of successful businesses in Lenox.  He added the Victorian front of the building in the late 1880s. As with many successful Lenox businesses at the turn of the century, he catered to the estate owners by providing lodging for their secretaries and horses for hire.




Redwood - 1881
Redwood – 1881

Redwood was built about 1880 for S. Parkman Shaw.  Later owners used the name Beechknoll.




Beaupre – Gone But Not Forgotten

Beaupre 1902-1961
Beaupre 1902-1961

George and Elizabeth Turnure built Beaupre in 1902 roughly where Turnure Terrace stands today.  The house picture here reflects alterations to an 1867 structure.  The 1961 fire was thought to have been caused by some Windsor School students.

George Turnure was a New York banker and the father of a 21 year old WWI flying ace.  His son was killed and, in his honor, George built  the Lenox Brotherhood Club on Walker St.  that would become the Lenox Community Center.

Lithgow – Gone and No Photos

This described in David Woods’ Lenox Massachusetts Shire Town (1969) as being on the west side of Lanier Hill on Old Stockbridge Road.  The house (apparently extant at that time) is dated to the late eighteenth century although “modernized” in 1870 by Alfred Gilmore.

Burton Harrison House

15 Hawthorne - Major Harrison House (Brook Farm Inn)
15 Hawthorne – Burton  Harrison House  – c. 1882; Now (Brook Farm Inn

In another example of cashing in on resort development, Frederick Rackemann  bought a local farm in 1882 and constructed this house for rental.  Rackemann was married to Elizabeth Dwight Sedgwick and lived at the Hive.

The first tenants were Burton Harrison and his wife Constance Cary Harrison. The cottage became known as “The Burton Harrison House.”

The Harrisons were originally from Richmond, Virginia. Burton Harrison served as the personal secretary to President Jefferson Davis. Constance was a direct descendant of Thomas Jefferson. After the Civil War the Harrisons moved north and became prominent members of New York society.

How Our Inn’s Berkshires History Is Tied to the Statue of Liberty
Like many of their contemporaries, the Harrisons chose to leave the city for the summer season. They rented the Lenox cottage and entertained their friends there. Guests included the Andrew Carnegies, Dr. Oliver Wendell Holmes, and the poet Emma Lazarus. Constance was a popular novelist and playwright. She enlisted some of her friends to act out parts of her plays in the library of the Lenox house.

In 1883 Constance chaired a fund-raising art exhibition. A statue was being given as a gift to the people of the United States, from the people of France, and New Yorkers were busy raising funds to construct a pedestal for the statue. Constance joined in this effort by gathering a portfolio of original literary works by leading American authors, which she planned to auction at the art exhibit. Constance asked her friend Emma Lazarus to write a sonnet for the occasion. Lazarus, a member of the Harrisons’ New York set, had been doing volunteer work at a Lower East Side settlement house. Constance suggested that Emma use that as inspiration and several days later received a copy of  the famous poem

Frederick Rackemann died in 1900, and  to his butler, James Whittenham. Whittenham was in the odd position of having the building, but no property on which to situate it. He purchased real estate on Hawthorne Street from Bertia Parsons, the widow of Julius Parsons. The cottage was moved down the hill, and found a permanent home at 15 Hawthorne Street.  It is currently operated as a bed and breakfast.

Parenthetically, on its way down the hill, the house passed the famous elm tree where a fatal sled accident had occurred. Lenox resident Edith Wharton later based her novel, Ethan Frome, on the accident. The tree was eventually removed, but a grassy triangle still marks the spot at the intersection of Old Stockbridge Road and Hawthorne Street.
It was purchased in the 1970’s by Ruth Backes, a direct descendant of Ralph Waldo Emerson. Her family history is important because Emerson was involved in the original Brook Farm, a utopian cooperative community of the 1840’s; Ruth Backes changed the name of the inn to Brook Farm Inn. Nathaniel Hawthorne was also involved in the original Brook Farm, and based his novel, The Blithedale Romance, on his experiences there. How ironic that the inn is located on Hawthorne Street!

(from Brook Farm Inn website)


Plumstead When Home of Joseph Whistler
Plumstead When Home of Joseph Whistler

A jail was among the needs Lenox had when it was the county seat (1784 to 1867).  Plumstead was the first site of the jail and the jailer’s house.  The jailer is also described as owning Blossom Hill Farm.  Part of the structures were burned down by a prisoner in 1814.  By the late 19th century

Plum stead (95 Old Stockbridge Road) - c. 18010
Plum stead (95 Old Stockbridge Road) – c. 18010

Queen Anne style angles had been added and one of two Lenox Whistler’s had moved in.  Joseph Whistler and his brother Ross (who purchased a house on Greenwood (now known as Whistler’s Inn) were nephews of James McNeil Whistler and grandsons of the famous “Whistler’s Mother.”

The Bishop Effect

Cortland Field Bishop
Cortland Field Bishop
Interlaken 1888-1922

Cortland Field Bishop (1870-1935) drove fast cars, invested in the Wright Brothers, wrote about history and collected books.  Like several of his Lenox estate owning counterparts, both his father and mother came from wealthy families.  His brother David committed suicide in 1911 and the entire family fortune came to Cortland. He used part of his fortune to buy up a number of properties in addition to those he inherited. His properties surrounded Bishop’s Estate (running from Old Stockbridge Road to Kemble Street across from Canyon Ranch) plus further up OSR (across from Elm Court) Interlaken.  He razed The Perch(off Kemble) and built the Winter Palace

He  razed Yokun Farm on Old Stockbridge Road and built Ananda Hall in 1927 (demolished 1940)

Yokun Farm - 1791
Yokun Farm – 1791

The original house on Yokun Farm had been built by the William Walker family (one of three Lenox properties William Walker owned) and passed to the Goodman family — perhaps after the Walkers moved to their house in town.

Ananda Hall was razed shortly after Cortland died and only a rock wall remains on Old Stockbridge Road. The Winter Palace he had built off Kemble remains.  The Bishop family also built two houses (for all those overflow guests!) on Walker Street that stand today.

The rest of the former and standing estates start bleeding into Stockbridge, but their owners probably would have socialized toward Lenox.

Allen Winden

Allen Winden - 1882
Allen Winden – 1882

Allen Winden was built next to where Yokun Farm had been and had a spectacular view.  The house, apparently named for a town in Switzerland, was built in 1882 by Charles Lanier (1837-1926) and Sarah Egleston Lanier (1837-1898).

Allen Winden Stables
Allen Winden Stables

Sarah was a descendant of Azariah Egleston, one of Lenox’s Revolutionary War heroes and early town leaders.  Lanier, a banker and investor, lived the good gilded age life with lavish hunt breakfasts and weddings in Lenox plus membership in the famous Georgia Jekyll Island Club and J.P. Morgan’s Corsair Club.  Good thing – since J.P. Morgan, a frequent business partner,  had to bail Lanier out a couple of times.

The elaborate house was demolished, after Lanier’s death, in 1926 and replaced by a plainer Henry Seaver design.  The elaborate landscaping was divided up into lots and it is now the Winden Hill Condominium complex.

Elm Court

Elm Court - 1886
Elm Court – 1886

This shingle style spectacular was another product of two fortunes marrying.  The original house was much smaller than the 90 room final product.  Designed by Peabody and Frederick Law

Emily Vanderbilt and William D. Sloane
Emily Vanderbilt and William D. Sloane

Olmsted, it was commissioned by William Douglas Sloane (1840 – 1915) and Emily Vanderbilt Sloane (1852-1946).  He was the son of the prosperous Sloane furniture business and she was the granddaughter of Cornelius Vanderbilt.

Miraculously, the property has survived and the current owners are seeking approval to build a luxury hotel around the gilded age complex.


The Lenox Hunt at Overlee - Built 1903
The Lenox Hunt at Overlee – Built 1903

Down the road toward Stockbridge, Samuel (1868-1923) and Elinor (1873-1961) Frothingham built Overlee in 1903.  As with so many of its wannabe Elizabethan counterparts in Lenox, Overlee replaced a shingle style home called Glad Hill (no pictures).  While

Overlee Residence of Samuel Frothingham - 1903
Overlee Residence of Samuel Frothingham – 1903

Overlee was being built the Frothinghams stayed at the Poplars across Old Stockbridge Road (also no pictures).  As the hunt club gather shown above suggests, the Frothinghams were avid athletes and were active in the hunt club, golf and gardening.

Before settling into its current role as the Hillcrest Educational Center, it had been, along with so many other former estates, a boys’ boarding school.


Merrywood in 2011 - In Its Last Days?
Merrywood in 2011 – In Its Last Days? – 320 Old Stockbridge Road

Colonial Revival Merrywood was built in 1882 by Peabody and Sterns for Charles Bullard (1857-1911).  He had grown up at Highwood and was the son of East India merchant William s. Bullard.

For awhile it was operated as a Music Camp.  Its  fate is uncertain.



The Poplars
The Poplars

Known to have existed near Bean Hill Road (the Frothinghams lived here prior to the construction of Overlee) but limited additional information.


For much more on the architecture of these houses and the people who lived in them, see

Houses of the Berkshires, 1870-1930, by Richard S. Jackson Jr. and Cornelia Brooke Gilder, Acanthus Press, 2006

The Berkshire Cottages, A Vanishing Era, by Carole Owens, Cottage Press, Inc. 1980

Lenox as a Resort – Yokun Ave. Cottages


Windy side - 1875
Windy side – 1875 (Lenox Library)

Windyside (111 Yokun)  was built  by Boston physician Richard Cranch Greenleaf (1845-1913) and his wife Adeline Emma Stone (1849-

Lenox Golf Club
Lenox Golf Club

1936).  It is notable as one of the few stick style wooden buildings still standing in Lenox.

History of the Lenox Club (and Windyside) Now Available
History of the Lenox Club (and Windyside) Now Available

For awhile, the it had the additional distinction of having one of the earliest American designed golf courses.

Upon Greenleaf’s death  in 1913 the house, outbuildings golf course and the entire ninety acres was purchased by the Club which moved in 1914 from its smaller club house on Walker St.

In 1924 the nine hole golf course was expanded to eighteen holes and the ‘Lenox Golf Club’ was formed in association with the Aspinwall and Curtis Hotels both of which used the course for their guests.
The arrangement lasted until 1932 when the Aspinwall Hotel burned. This event and the difficult financial situation caused by the Great Depression led to abandonment of the golf course which gradually became replaced by a heavily wooded forest.
Interest in the Club was revived and major improvements to the clubhouse and grounds were initiated in the 1980s.The course was expanded in the 1920’s and shared with the Curtis and the Aspinall.  The destruction of the Aspinall and the general financial mayhem of the 1930’s made the gold course unaffordable and it is now grown in.  Fortunately, the Lenox Club was revived in the 1980’s and the building survives as a private club.

Ethelwyn/Ethelwynde I and II

Ethelwyn - 1875
Ethelwyn – 1875
Henry Braem
Henry Braem

In 1875 Henry Braem (associated with the Cunrad Line and ambassador to Denmark) built the original Ethelwyn (or Ethelwynde) off Yokun Ave.  Then as now, his neighbor was Windyside (now the Lenox Club) built around the same time.

In the 1870’s Henry also built a model farm on Undermountain Road.

In 1893 he sold the estate to the widow of Robert Winthrop who was also the mother of Grenville Winthrop, who would go on to build Groton Place in 1905

"Grandma Winthrop" Lived at Ethelwyn owned Ethelwyn until 1925
“Grandma Winthrop” Owned Ethelwyn until 1925

on West. St.  The Wintwops were “those” Winthrop’s who led the great migration and had generations of wealth and notoriety.  Mrs. Wintrop (ne’ Kate Taylor) was wealthy in her own right.  Her father had been a partner of Cornelius Vanderbilt and first president of City Bank (predecessor of the modern Citibank).

Mrs. Winthrop was, not surprisingly, a social leader in Lenox and New York.  Among other things, she was active in the summer garden club competitions (think Downton Abbey).

Ethelwyn (Ethelwynde) II (111 Yokun) - 1928
Ethelwyn (Ethelwynde) II (111 Yokun) – 1928 (Lenox Library)

In 1928 the house was purchased by Halstead Lindsley.  He tore down the wood framed original house and had a local architect, Benjamin Greeley, construct the modern Tudor-style mansion that stands today.  Recently operated as an upscale cultural retreat, it is now a private home.

Stonover I and II

 Stonover - 1875
Stonover – 1875

Ethelwyn had Winndyside as a neighbor on one side and Stonover as a neighbor on the other. Still a lovely street today, Yokun Ave. was newly created in 1874-1875 and must have been quite spectacular from the 1870’s on.

John Parsons
John Parsons

Stonover was built by John Edward Parsons, (1829-1915) a New York Attorney. Among others, his clients included the American Sugar Company. He defended them to the Supreme Court in an anti trust case – very Gilded Age!
The estate spread from Yokun to Undermountain Road and encompassed

Drive on Stonover Property
Drive on Stonover Property

the area now known as Parson’s Marsh. the still standing Stonover Farm and over Lenox Mountain to what is now the Audubon Bird Sanctuary.

His son Herbert

Stonover Farm - Undermountain Road
Stonover Farm – Undermountain Road

inherited the farm (and died there in the 1920’s a freak accident). His daughters (Mary and Gertrude) inherited the house and after some adventuresome travel, re-invented it in 1921 with a Delano and Aldrich design.

Stonover II - 1921
Stonover II – 1921

They moved the house further back on the property, dispensed with the turrets and mansard roof and created a sleek stucco house that became a center of mid 20th century culture with speakers like Alexander Kerensky. Mary (Gertrude died in 1927 on a trip to Italy).

Mary donated the Pleasant Valley Bird Sanctuary in honor of her two deceased siblings.  In a move of less certain long term value, she became interested in re-populating local beavers (hence Parson’s Marsh.)

Stonover II was demolished in 1942 and replaced with a 20th century house.

Gusty Gable

Gusty Gables 1879
Gusty Gables 1879 (Lenox Library)

Shortly after Yokun Ave. opened Mary de Pester Carey Sr.  (in her ’60’s at the time), her daughter Mary de Pester Jr., and a close family friend, Katherine Buckley Sands pooled their resources to purchase a five acre plot and build

Charles McKim (1847-1909)
Charles McKim (1847-1909)

Gusty Gables.  The Colonial Shingle Style home is the only surviving Lenox design of Charles McKim.

The survivor of the three, Mary Carey, was an avid horsewoman and active in the Village Improvement Society. She, with Edith Wharton and Florence Sturgis awarded prizes for the best-kept village lawns and front gardens.

Gusty Gables (75 Yokun) as it Appears in 2016
Gusty Gables (58 Yokun) as it Appears in 2016

Carolyn Cobb, a later owner hired Pittsfield architect Henry Seaver to update the McKim design to a more formal Colonial Revival style.  The building survives as a private residence.



View of Stonover from Edgecombe Drive

The ladies of Gusty Gables must have been pleased when their New York friend, Miss Clementine Furniss decided to build Edgecombe next door.  The

Edgecombe - 1880
Edgecombe – 1880
Edgecombe Caretaker Cottage
Edgecombe Caretaker Cottage

whimsical and rambling building apparently still standing in the mid 1980’s  at the corner of Yokun and Sunset (it’s mentioned in Carole Owens’ The Berkshire Cottages) 

The caretaker’s cottage (much altered) still stands on Sunset.


For much more on the architecture of these houses and the people who lived in them, see

Houses of the Berkshires, 1870-1930, by Richard S. Jackson Jr. and Cornelia Brooke Gilder, Acanthus Press, 2006

The Berkshire Cottages, A Vanishing Era, by Carole Owens, Cottage Press, Inc. 1980

Lenox as a Resort – Walker Street Cottages

*The Bishop Guest Houses

35 Walker St.
35 Walker St.
45 Walker St
45 Walker St.

Thirty five and forty five Walker were built as “overflow” guest houses for the Bishop family

Thirty Five, called the Henry W. Bishop House was built in 1885 and is currently (2016) an inn.

Forty Five, called the David W. Bishop House was built in 1895 and is currently offices.


51 Walker St., Harley Proctor House - c. 1912
51 Walker St., Harley Procter House – c. 1912

Built as a summer home for Harley Procter, the classical revival style house is said to have been designed to resemble a bar of Ivory Soap.

Harley Procter, son of one of the founders, introduced many of the concepts of modern advertising and marketing.  He  presumably cashed in big when the P & G partnership incorporated in 1890.

Henry Proctor (1847-1920)
Henry Procter (1847-1920)

The Procters occupied the house for just a short time, selling it in 1919 to Graham Root, who used it as a real estate office. Subsequent uses included a charm school in the 1930’s, a guesthouse, and office space. In 1942 it became Gateways Inn, by which name it is still known.

*The Old Lenox Club/Community Center

The Old Lenox Club - 1860's?
The Old Lenox Club – 1860’s?

Heaven forbid the gentleman visiting their estates in Lenox should be without a place to hobnob, so they founded the Lenox Club in 1864.  They built a “modest” (at least in terms of the excesses of the day) clubhouse mid century and proceeded to bowl in their own

Screen Shot 2016-01-28 at 7.14.57 PM
On the Porch of the Old Lenox Club (Lenox Library)

bowling alley, smoke cigars, play cards, etc. It was incorporated as a reading club for gentlemen in 1874.

Later the club leased a nine-hole private golf course off Yokun on property belonging to Dr. John C. Greenleaf.

In 1914, after Dr. Greenleaf’s death,  the house, outbuildings golf course and the entire ninety acres was purchased by the Club. In 1924 the nine hole golf course was expanded to eighteen holes and the ‘Lenox Golf Club’ was formed in association with the Aspinwall and Curtis Hotels both of which used the course for their guests.
The arrangement lasted until 1932 when the Aspinwall Hotel burned. This event and the difficult financial situation caused by the Great Depression led to abandonment of the golf course which gradually became replaced by a heavily wooded forest.
Very active interest in the Club was revived and major improvements to the clubhouse and grounds were initiated in the 1980s.

Community Center (65 Walker) - 1924
Community Center (65 Walker) – 1924

In 1921 George E. Turnure purchased the Walker St. site and built a new community center in memory of his son who had been killed in the First World War. This new community center became the home of the Lenox Brotherhood Club, an organization made up of the union of the Men’s clubs of the Episcopal and Congregational Churches. The community center provided recreational facilities such as a tennis court, billiard room, gymnasium, and bowling alley. The center also has a large hall and stage. Membership in the club expanded in the 1930’s and eventually became open to all. It is currently owned by the Town of Lenox, and provides programs for the community such as the Council on Aging for seniors, youth programs, fitness classes, and meeting space.

*Pine Acre

Pine Acres (81 Walker St.)
Pine Acre (81 Walker St.) – 1885

Mrs. M. E. Rogers of Philadelphia had this house built in 1885, for use as a summer residence. By 1890 the house had been rented for the season to John Burrell, and in 1892 it was sold to Nancy W. Wharton (Mrs. William C.) who summered here with her daughter.

Mrs. Wharton’s son, Edward, (1850-1928) was

Edward (Teddy) Wharton
Edward (Teddy) Wharton.

married to novelist Edith Wharton who was to become one of the most illustrious residents of Lenox. After spending several summers in Newport, Edith Wharton, displeased with both the climate and the lack of intellectual life there, came to Lenox. She stayed at “Pine Acre”, home of her mother-in law and sister-in-law, who were abroad at the time. She was very impressed with Lenox that she returned to “Pine Acre” the following summer and, in February of 1902, returned to Lenox to look for a house site of her own. While looking for the site she stayed at the Curtis Hotel. She spent one last summer at “Pine Acre” in 1902, while her house, “The Mount”, was under construction.

Mrs. William C. Wharton continued to stay at “Pine Acre” for several summers until her death in August of 1909 in Lenox.  Teddy Wharton spent many of his declining years here after he and Edith divorced.

For awhile the property was run as an inn and known as “Three Gables,” or “The Gables.”  It is currently (2016) condominiums.

*Col Oliver House

Screen Shot 2016-01-28 at 4.45.30 PM
91 Walker St. – 1895

This property was originally owned by William T. Walker and his wife and was sold to Edwin Spencer in 1852.  Mrs. Marion R. Oliver built this house on the site of an earlier house, built by Edwin (Edmund?) Spencer in 1852,  and by 1896, had the original house demolished and a more fashionable one built in its place. In 1896 the property was sold to Mr. and Mrs. John Struthers, frequent summer visitors to Lenox. The Struthers’ christened the house “Wynnstay.” and used it for many years as a summer residence. It is currently operated as an inn under the name “Hampton Inn.”

Ventfort Hall

Bel Air/ Vent Fort
Bel Air/ Vent Fort

Ogden Haggerty, a successful banker and intellectual, had been visiting the Wards and the Sedgwicks for a number of years and often renting a property from Mr. Stanley located where Ventfort Hall is today.  In 1853 The Haggertys purchased the property and built a home of their own.

Ventfort (104 Walker) - 1893
Ventfort (104 Walker) – 1893

In 1891, Sarah and George Morgan purchased the property, moved the original Vent Fort across the street, and used Rotch and Tilden to build a Jacobean mansion of their own.

The original Vent Fort was being used by Lenox Country Day school when it burned in 1961.  Much of the extensive average of the Morgan’s Ventfort were sold off for Morgan Manor and individual house lots.  The mansion sits on the remaining average and has been restored and is open as a Museum of the Gilded Age.

*Sunny Bank

Sunny Bank - 1865
Sunny Bank – 1865

This wood frame home was built in 1865 for General and Mrs. F. C. Barlow.   When the Bruno Aron family was running Ventfort Hall as Festival House, Sunny Bank was used for overflow guests.  It is currently a private home.

Francis C. Barlow
Francis C. Barlow

Francis Channing Barlow (1834-1896), despite his obvious youth in this photo, became a general by the end of the Civil War.  In the small world category, he married, at the end of the war, the sister of Robert Gould Shaw who had married Annie Kneeland Haggerty and honeymooned at Ventfort Hall.  A lawyer by training, F.C. Barlow founded the American Bar Association.


Thistle wood - 1887
Thistle wood – 1887

In 1887, Mr. and Mrs. David Lydia needed an escape from Westchester.  The family estate, West Farms was being incorporated into the Bronx.  They hired Rotch and Tilden to build the lovely Colonial Revival at 151 Walker St.  The interior has been significantly altered but the exterior and grounds remain quite similar to the original design.  It is a private home.


*Technically these were just very nice summer homes – not quite up to the gigantic scale of the “cottages.”


For much more on the architecture of these houses and the people who lived in them, see

Houses of the Berkshires, 1870-1930, by Richard S. Jackson Jr. and Cornelia Brooke Gilder, Acanthus Press, 2006

The Berkshire Cottages, A Vanishing Era, by Carole Owens, Cottage Press, Inc. 1980