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  • Writer's pictureJames Dean

Architect, Pioneer, A Woman of Vision, Enigma: Theodate Pope Riddle 1867-1946

As a graduate of Avon Old Farms School in Avon Connecticut, I was always fascinated by the history of its founder, a woman Theodate Pope Riddle, ironic given Avon Old Farms is a private men's preparatory high school for gifted students. It wasn't till years later after graduating that I would go on to learn the inspiring details about the life of Theodate Pope Riddle (1867-1946). And what I discovered was that Ms. Riddle's life story reads like a Hollywood movie script. From an early age, she was a woman who refused to be confined by the limitations of her time. Born in 1867 into wealth and privilege in Cleveland, Ohio; she broke societal norms to become one of America's earliest female architects.


Early in her life, Theodate attended the prestigious Miss Porter's School in Farmington, Connecticut, a finishing school known for preparing young women for society. This experience likely sparked her lifelong interest in education. But, her story is about more than just buildings; Ms. Riddle was an educator, a spiritualist, adventurous and a complex figure shaped by wealth, personal tragedy, and a boundless desire to leave her mark on the world. 



Building a Legacy, One Stone at a Time

While best known for her architectural projects, Riddle's independent streak began early. After finishing school, and still of relatively young age, she embarked on an adventurous European journey, soaking up the grandeur of old-world architecture. Upon returning inspired, she set out to become an architect – largely through self-study – a bold feat for a woman in the early 20th century.


Today, Ms. Riddle's work remains embodied in traditional styles, favoring Tudor and Cotswold designs that echoed the villages she had admired in England. Among her creations are Hill-Stead, her family home-turned-museum in Farmington, Connecticut, and the Westover School, an all-girls institution she founded in Middlebury, Connecticut.


The Jewel of Avon

But Theodate Pope Riddle’s crowning architectural achievement was the Avon Old Farms School in Avon, Connecticut. Established in 1927, the campus is a masterpiece of architectural nostalgia built to resemble an idealized English village. She employed over 500 workers, many master-craftsman (1923 - 1926) which she brought from England to build the school in America. Here, Riddle's design philosophy extended beyond aesthetics. She envisioned an educational environment that emphasized experiential learning, personal growth, and a strong moral compass. And today, Avon Old Farms School stands as one of the most prestigious private educational institutions in America. Watch Avon School Video



More Than an Architect 

Ms. Riddle was a fascinating mix of contradictions. A woman of substantial wealth, she championed progressive educational ideals. She was drawn to the paranormal, spiritualism, and progressive medicine, yet her designs were firmly rooted in the tangible world. Among her many adventures, Theodate Pope Riddle was a survivor of the RMS Lusitania ship sinking which she narrowly escaped, but she faced personal loss and the realities of a rapidly changing world. These experiences undoubtedly shaped her outlook and determination.


A Force of Nature

Historically, without a doubt Ms. Riddle was a trailblazer who defied convention, a visionary far ahead of her time, an unusually peculiar woman with boundless ambition. Her architectural works are a visible testament to her artistic vision. But more importantly, her legacy rests in the ideals of education and character that she fiercely championed. Her story is one of both substance and style, a reminder that the most enduring contributions often lie beyond the purely material.


And while researching this article, I came across perhaps Ms. Riddle’s most insightful gift, if we can learn anything from Theodate’s diaries, it’s that money does not insulate an individual from inner conflict. There’s nothing “exact” about Theodate because she was so painstakingly in tune with reality, curious about death and what it meant to be a moral person. Her spirited writing shows a mind willing to make errors and wild speculations that excited her imagination, eventually leading to her conception of Hill-Stead, and Avon Old Farms, both examples of her grand physical legacy.


Theodate also left a silent wealth of primary documents for curious Archives interns and those interested in local history, to discover and marvel at, despite the indifference of anyone else—it’s the connections that one discovers on one’s own—her understanding of art and commerce, her relationship with her father, her strained relationship with her mother, her want of both solitude and companionship, the value placed on her female friendships, her cinematic escape from the Lusitania which she somehow almost seemed to have resented surviving as reflected at times in her diary notes —The list goes on.


Often baffled by her own fortune, Theodate was aware of her own flaws—even worked aesthetic flaws into her architecture to evoke emotion and meaning. Resigned to womanhood (then a bit of a curse) but determined to transcend its bounds, she was exhaustively seeking her true self, aware of her privilege, thankful for it, but unsettled. 


Theodate Pope Riddle was undoubtedly an enigma, a true pioneer, a leader, a fascinating character in American history that deserves further recognition and studying which I believe could be of particular educational value for young people. Even today, Ms. Riddle remains a fine example of genuine entrepreneurship. And throughout her life, she focused on accomplishing her passions and purpose, despite the cultural and social barriers of the time. In fact, she unashamedly transcended any limitations or stigmas that others might place on her. And studying Riddle's life, it holds insightful lessons of value that still apply to this day.    


James Dean, author / eCommerce guru is located in Northeast Ohio with over 35 years of experience in Business Development. He is a graduate of Boston University. J Dean leads a team helping entrepreneurs, corporations and non-profits to succeed in a changing world. Questions contact 440-596-3380 or Email jdean@entangledvibrations.com   


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