Holstein herd
Milking Time

The Walter Cass Jennings Family

Walter Cass Jennings and Lillian Soule Jennings
Walter Cass Jennings and Lillian Soule Jennings at home
Walter Cass Jennings and Lillian Soule Jennings
Nice boots.
The Jennings Farmhouse
The Jennings homestead on Jennings Road, Kent, late 1930s

Jim Jennings, Lucy Seger’s husband, was one of ten children of Walter and Lillian Soule Jennings, who owned a substantial farm with a herd of registered Holsteins on Geer Mountain.

Walter Jennings was remembered with deep affection by his children and grandchildren: tall, witty, with a good sense of humor. As a young man he taught school for a year or two before taking up farming. At age twenty he married Lillian Soule Cable, a 24-year-old widow with a five-year-old daughter, Lena. Walt Jennings bought the farm property at the top of Geer Mountain, along what is now Jennings Road. They lived there for the rest of their lives.

Jim’s younger brother Dick married Lucy’s younger sister Jnet and lived at the farm, raising their two sons, Stanley and Arnold (Arnie). Lillian was afflicted with severe arthritis and spent her later years as an invalid. Jnet maintained the house, raised her boys and took care of her mother-in-law until Lillian’s death. After Dick’s parents’ death, he and Jnet lived at the farm until they sold it in the 1960s, then moved with Arnie to a house on a parcel of land that had been part of the original Seger farm, a house my parents built in the early 1950s.

Jnet Seger Jennings and Lillian Soule Jennings
Jnet Seger Jennings and Lillian at home

Jnet Seger and Richard Jennings
Jnet and Richard Jennings
Jnet Seger and Richard Jennings
Remodeling the farmhouse
to accommodate Dick and Jnet.

When Dick and Jnet Seger Jennings moved into the Jennings Road farm an addition was added for them and at that point an indoor bathroom was added to the house. Like many people of their generation, Gram and Gramp Jennings felt that an indoor toilet was unsanitary.

Holstein registry
Registration for Airymore Isabella, 1934
Holstein registry
Verso of Isabella registration,
Gramp Jennings in background of upper photo

The Business of Farming

Walter ran a sophisticated operation for the time. He had a herd of registered Holsteins, and kept production records for each cow. Author and Kent resident Phil Camp’s reminiscences include buying high-quality milkers from the Jennings farm. Beyond the house was an orchard.

Lillian Soule Jennings at home

Poultry at the Jennings farm

Lillian rarely left the farm and ran an egg and poultry business, trading with a local grocer for the few items that the farm didn’t produce.


While examining the Holstein registration forms, I noticed that these were a source of more photos of both the barns and some of the family. Below are two photos with female figures. The seated figure with exposed knees looks like Irene Jennings Grisell, who at the time of this photo would have only been 10 or 11 years old. The face appears more mature, but the demeanor is that of a child. Irene’s face in other childhood pictures is long, lean and fairly mature looking. The second young woman is at this point unidentified.

Jennings daughters  Jennings daughters  Jennings farm 

Family Connections

Haying: Walter Cass Jennings at left; his son Richard (Dick) Jennings on wagon. Standing, left to right: Nat Ashman, Lester McNamara; and Dave Middlebrook.

farm labor

Three sources helped identify the men in this photograph and provide some context. Nat Ashman was a blacksmith who worked at Brown’s Forge in Gaylordsville, a few miles south of the Jennings farm. He was also a relative.

Stan Jennings remembers Dave Middlebrook at the farm: “Dave Middlebrook was a cabinet maker from Bridgeport who spent a month for his vacation at our farm helping with haying and usually doing some sort of carpentry project. I'm sure no money changed hands for the arrangement.

“I remember Dave coming every year until about 1948 when he retired from his business. He drove a circa 1938 Plymouth woodie station wagon.”

Lester McNamara presents us with a new puzzle. His granddaughter found a rather distant DNA connection to the family via the Ancestry.com DNA database. She contacted us to find out more about that, and a 1934 Kent Probate Court document that appointed Clarence (Jim) Jennings, Walter’s son, as guardian of Lester’s estate when Lester was nineteen and his mother was living in South Kent. His mother is described as “guardian of his person,” but the custodianship of his bank account was assigned to Jim, (who also deposited a $1500 bond of surety). Witnesses were Albert Chase and Dick Jennings.

A portion of the probate document summarizes:

Billy and Lester McNamara, early 1940s.
Lester served in the National Guard.

ORDERED: that said Clarence Jennings, Guardian, deposit the sum of One Thousand three hundered ninety two and 79/100 (1392.79) dollars represented as the whole of said Estate in the New Milford Savings Bank of New Milford Connecticut, and it further

ORDERED: That no part of said principal sum of said amount shall be withdrawn from said Bank without an order from this Court.

Stan Jennings: “I remember Lester being at our farm from time to time when I was maybe 6 to 10 yrs. old. We went to visit Lester and his wife (her name was Mary) and his kids. Billy is the oldest and is a year older than me. Lester and his family also spent a week or so one summer camping in a tent in one of our fields close to the house.

“I had previously thought my father was Lester’s guardian, however, it was Clarence. Why he seemed to have spent more time at our farm, I don't know. I do know that he and my father were close.

“His mother was Mary Lucy Chase, who married a John McNamara who had died before Lester was born.”

Random Photos

Lillian Soule Edgar Benson Soule Sarah Jane Cass Jennings Sarah Jane Cass Jennings  cows  Jennings grandparents unknown

Walter and Lillian Jennings’ Children

A work in progress. Many photos of the family and the siblings’ children have survived. I hope to build an active link to a photo album page for each. In the meantime, click on any thumbnail for a larger image and more information.

children  Dick children  unknown  Jennings daughters  unknown  Dick  unknown  unknown  Jenning/Cass daughters
Walter Cass Jennings, son of Elroy Seymour Jennings and Sarah (Cass) Jennings,
b. 1 Jul 1868 d. 17 Jun 1945
Married Lillian Soule Cable, daughter of Edgar Benson Soule and Sarah Wheeler,
(7 Jun 1864-4 Aug 1950) on 5 Sep 1888
Both buried in Good Hill Cemetery, Kent, Connecticut.
50th Anniversary
50th Anniversary, 1938.


and many photos of children, grandchildren and schoolmates…

Jennings daughters  Jennings daughters  Jennings daughters  Geer Mountain School unknown unknown  unknown unknown unknown unknown Stan and Arnie Ethel Jennings unknown unknown Donna and Susan unknown

The Family of William Edgar and Caroline Brown Jennings

Bill Jennings became the blacksmith at his father-in-law’s shop in Gaylordsville, which is still known as Brown’s Forge. Bill and Caroline raised their children in the white farmhouse across the road and railroad tracks.

This property and the fields and barns accompanying it were eventually sold off. A small barn bermed into the steep hillside closer to Waller Road was converted to a house. In the early 1960s Impressionist painter Bernard Lennon and his wife Ruth bought the converted barn, which became part of an informal artists’ community. Painter Richard Stalter moved from Ohio to join the group and bought the Jennings farmhouse.

The property has figured in many of the works of these and other artists. The barn is now the studio and home of Bern’s student Susan Grisell, great-niece of Bill Jennings and granddaughter of Jim and Lucy Jennings.

Bill Jennings house
View of the Bill Jennings home by Susan Grisell:
“Heavy Snow,” oil on linen panel, 12x12 inches
Ethel Jennings Amos Jennings Bill Jennings  Maybelle Jennings Ethel Jennings Ethel Jennings Thomas Wedding

The Family of Roy Cass and Lena Florence Wheeler Jennings

Roy and Lena Jennings Roy Jennings Roy Jennings Roy Jennings family Roy Jennings family Homer Myron Bertha Jennings Jennings

The Family of Sarah Louise Jennings and Walter Conn

Sarah Jennings and Walter Conn

Sarah Louise, b. 2 Aug 1892 d. 14 April 1996; m. 14 Nov 1918 Walter Denny Conn b. 24 May 1895 d. 14 April 1979, New Milford, CT

Sarah Jennings was a teacher in her early years. Walter Conn’s parents operated a farm in the Bulls Bridge section of Kent. Walter opened Conn’s Dairy in New Milford in 1939.

They had six children:

Their son Walter Jennings Conn took over the commercial dairy and supplied bottled milk to towns in the region into the 1960s, as well as milk cartons for school lunch programs. He was active in New Milford town affairs and much loved throughout his life.

A Child’s View…

Book Cover

In the early nineteen teens Walter (Sr.) and Hannah Denny Conn hosted a city family in the summers, who came up to South Kent on the train and whose two daughters enjoyed a very different life than that of their home in the Bronx. In 2012 the reminiscences of Bertha Fisse Robbins and Edyth Fisse Emanuelson were published as Cows Do So Make Milk and other Oddities. The little book is replete with photos of the Conn’s Riverside Farm and descriptions of the activity at the busy farm from a child’s perspective. A half-century after their summer sojourns they contacted Walter D., whom they knew as a boy. He invited them to his home, introduced them to his wife Sarah and their children, and revisited many of the places they had visited 50 years before. A pdf of the book with charming photographs can be read here.