Greens Farms Academy is a PreK-12, coed school in Westport, CT

Love Letters from a Patriot: An Interview with Elinor Upton Biggs '64

Love Letters from a Patriot: An Interview with Elinor Upton Biggs '64
Head of School Bob Whelan, Elinor Upton Biggs '64, and former trustee Samantha Mooney

Pictured: Head of School Bob Whelan, Elinor Upton Biggs '64, and former trustee Samantha Mooney


Elinor Upton Biggs ’64 attended The Bolton School for many years before transitioning to boarding school in 9th grade. Her father, John D. Upton, played a pivotal role as one of the founding Trustees of what would become The Kathleen Laycock Country Day School, and later, Greens Farms Academy. On her mother’s side, she is the great-great-great granddaughter of famed Circus man, P.T. Barnum. Elinor’s first book, The Pig with No Name, is a heartwarming and informative children’s story about a pig whose parents forgot to give him a name. With her second publication, Love Letters from a Patriot, Elinor takes a deep dive into WWII and explores the more than 200 letters her father, Jack, sent home while stationed overseas from July 4, 1942, to September 13, 1944.

"Publishing Love Letter from a Patriot has been an absolutely fascinating process," said Elinor, in an interview with Ana Holwell, GFA’s Director of Alumni Relations. "It took two years and two months to finish it, which is almost the exact same amount of time my father was overseas. It’s funny how life has these strange little connections.

My father decided to enlist in the Army in January 1942, one month after the bombing of Pearl Harbor. He was able to enter at the officer level having enlisted in ROTC at Yale. Many people wrote letters home at that time, but a lot of them were more along the lines of, “Hi, I'm okay.” I don’t think everyone was as conscientious as he was. He kept a log of his letters and wrote often, but there was so much he couldn’t say. The whole time he was fighting in North Africa, Sicily, and other parts of Italy, he couldn't tell my mother where he was, which was another level of ambiguity that was unsettling for him and my mother.

Through the thickest of times, he still wrote home. Sicily is a very short chapter in Love Letters from a Patriot, but Dad said that it was the hardest of all for him. History may maintain that mainland Italy was probably the toughest, but because of the brutal battles he and his men encountered, it was Sicily. It was also significant because General George Patton assumed military leadership for the Invasion of Sicily and Dad greatly respected Patton for his military abilities and as a leader who got things done, though he did not respect his personal behavior. So while his time in Sicily was short and limited in letters, it was very significant in several ways and he wrote as much as he could whenever he could.  

He never spoke about the war. There was a code of silence, particularly for the soldiers of “the Greatest Generation.” When he returned home, my parents had an apartment in New York situated along the flight path of LaGuardia airport. The first night he came home, an airplane flew over their apartment building and he reflectively dove under the bed, like he was diving into a foxhole. They didn’t talk about it much but it was extremely scary for my mother. I can’t even imagine what the adjustment was like. I think the letters they shared throughout the war helped them to keep a perspective of who they were and to be the same people as best they could be in the circumstances.

After the war, my father became involved with The Bolton School because my older sister, Mary, went there, and then I followed. He helped with the acquisition of the Vanderbilt mansion and a few of them put the whole deal together. Education was always important to Dad. His father left the family when he was around 18. My grandmother was left with my dad, his brother had just died, and they were in a difficult financial situation. Dad was very fortunate to get a scholarship to The Hotchkiss School and then Yale which, along with his part-time work, allowed him to gain an excellent education. The experience of the scholarships and the value of his education were very important to him and led to him providing opportunities to help others achieve their educational goals. 

At The Kathleen Laycock Country Day School, Dad established the Upton English Award for the perception, appreciation, and scholarly interest in the study of English. He also set up the Upton Faculty Enrichment Fund to support and encourage professional development. That was something he felt very strongly about. He brought the idea to the school and gave the seed money to fund it. Additionally, there was a guest house on our property, which he offered, rent-free, to teachers in need of housing during the academic year. His philanthropic contributions epitomized his commitment to education and academic excellence, which was something that transcended throughout his life."