immediately left for America. Soon after her arrival, she met with the school’s trustees and told them that she was alarmed that Miss Porter’s legacy was in danger and proposed that they help Mrs. Dow and herself start a new school together. Perhaps because Miss Hillard admitted to doubts about giving up her position at St. Margaret’s, or because her relationship with the older woman was strained, or because of the astonishing fact that she intended to open a school in Farmington whether the other woman went along or not, nothing ever came of her proposal.
Still, in that encounter Mary Hillard revealed how sure of herself she had become after her successful years at St. Margaret’s. “I know school affairs thoroughly,” she told the trustees of Miss Porter’s. “It is my business. I know [the] ins and outs of school management as only one in school work can know them … points so essential that to ignore them means failure, while at the same time they are so obscure that only the experienced mind understands their importance … Moreover, the talent for success is extremely rare. I might almost say that in the last six or seven years there has not been a change of importance in any important boarding school for girls in the East without my having been asked to come in or lend a hand by advice or help find someone to run the school.”
Despite her faith in herself, she was soon to be shaken to her core. Toward her younger brother John, who was born when she was fifteen, Mary had always acted like a parent, directing his education and planning his life. After graduating with high honors from Yale, he began to practice law in New Haven. In August of 1903, a few weeks after his sister returned from Europe, he contracted typhoid fever after boating on the Farmington River. He hung onto life at Hartford Hospital for a few weeks, but in late September he died at the age of twenty-six. John’s death, their eldest sister Martha acknowledged, was the worst grief of Mary’s life.
Like many other freethinkers at the time, Theo had become fascinated by what was called “psychical science,” the investigation into the unknown and the unconscious. In an effort to ease her friend’s grief, Theo suggested that they try to communicate with her brother. Harvard psychologist William James, who had started the American branch of the Society for Psychical Research in Boston, recommended that they see Beacon Hill psychic Leonora Piper. A few months after John’s death, they had their first sitting to try to talk to his spirit. In the first session Mrs. Piper told Mary to tap her fingers, and then told her that her brother wanted her to remove her hat so she could hear him better. Mary became a true believer, and on John’s tombstone she had the following words inscribed: “He Being dead yet speaketh.” The séances continued intermittently until the end of 1907, when the plans for Mary’s new school got underway, and she supposedly became more concerned about her reputation. There’s another story that she stopped because she found it all “a little too exciting.” It’s doubtful that she abandoned her belief in the unknowable; it’s more likely that she convinced some of her colleagues of it. Years later Theodate’s young twin cousins spent a weekend with her and heard about inexplicable phenomena. When they returned to Westover, where they were pupils, and described this to Helen LaMonte, she did not disillusion them. Instead, Miss LaMonte pointed out that before the invention of the telephone, the idea of someone in America talking to someone in Europe would have been unbelievable, so that if one does not understand something, it does not mean that it does not exist.
After the months in Europe, it was more evident than ever that the growth of Waterbury in the 1890s had become “phenomenal,” to use Mary Hillard’s word, as immigrants arrived to work in factories that were polluting its air with coal smoke. The city had, in fact, more than doubled in size since she had moved there. At a time when there was no cure for tuberculosis, Waterbury and other cities were dangerously overcrowded. Teachers and parents alike had begun to believe that the countryside was a more wholesome place for schoolchildren than a city. And, as a result, Mary believed that St. Margaret’s School was in peril.
Not only did Mary want to get away from the unhealthy conditions of Waterbury, she also wanted to offer girls the athletics and other advantages that were more available in the country. Most important of all, she fervently wanted to create a self-contained community devoted to teaching traditional moral values to daughters of the newly wealthy merchant class. By then in her forties, Mary Hillard was a self-possessed person with a regal bearing. Her dream was a real possibility because of her manner and persuasiveness with the St. Margaret’s board of trustees as well as her friendships with the Popes and other wealthy and influential Connecticut families. At a time in America when a newly emerging crusade for rights for women was gathering force, Theo’s resources and determination to build another building and Mary’s success as an educator and her missionary zeal were a potent combination.
Their plan emerged for a girl’s school for one hundred and forty boarders and their teachers. Mary and Theo had joined the Connecticut Society of Colonial Dames together in 1900, and the ultimate design was heavily influenced by the colonial revival style. It was not necessary to be licensed to work as an architect in Connecticut at the time, and Theo hired draftsmen and consultants as needed. On January 30, 1906, Mary proposed to the St. Margaret’s board that they build a new school building outside Waterbury for the boarding pupils; they eventually agreed to the idea, even permitting her to take along the boarders and teachers who wished to go with her. Then, after someone remembered that the school charter did not allow a move out of Waterbury, the board agreed to release Mary from her contract. When she handed in her resignation exactly a year later, she was asked to withhold it until the end of the school year, and she agreed.
Mary’s plan was already in place, however. In 1903 she had told the Miss Porter’s trustees of her plan to form a company and issue stock in it to raise the $200,000 to $300,000 that a new school would cost, explaining that a well-managed school was “an extremely good investment.” Four years later in 1907, she set up the Westover Corporation to sell three thousand shares of stock at a hundred dollars each, which would pay an annual dividend of six percent. She sold stock to everyone she knew—friends, relatives, parents of pupils—even St. Margaret’s trustees. The man who immediately bought the most stock was John Howard Whittemore of Naugatuck, a man of her father’s generation whom she had met through the Popes. After making his fortune in malleable iron castings, he had commissioned a number of McKim, Mead and White buildings in his native city. Mary knew how to appeal to Mr. Whittemore, since they were both descendants of old Connecticut families and children of Congregational ministers. She praised his philanthropy as “a true and honest source of right and high minded influence,” and, after receiving a grateful letter from her in 1907, he called his help “a labor of love.” After selecting the rose as the new school’s flower, she sent the Whittemores roses at Christmastime; she would also ask him to light the first fire in a school fireplace. After the pupils arrived in Middlebury, Mr. Whittemore used to ask her, “Are the girls happy?” He was the first president of the Westover Corporation and then the first president of the board of trustees until his death in 1910, a year after the school opened.
Theodate Pope around 1895. ARCHIVES, HILL-STEAD MUSEUM, FARMINGTON, CT.
It was because of the Whittemores that Mary’s school was built in Middlebury, where the family had a summer home, Tranquillity Farm. Before land was bought, the Popes’ chauffeur, Turner, used to drive Mary, Theo, and teachers at St. Margaret’s around the countryside in the family convertible motor car, nicknamed the “Yellow Peril” for its color, looking for sites for the school. (It was the first automobile that Mary had ridden in, and at first she had been fearful of its great speed.) They had driven through Middlebury in 1906 but considered it too isolated; the village had been bypassed by industrial development because it lacked waterpower, and most of its eight hundred residents still worked the land. But after Mr. Whittemore and his influential friends pulled strings, an electric trolley line was built from Waterbury to Woodbury with a stop in Middlebury, and it was possible to transport laborers and, eventually, students to the village.
With the help of John Whittemore and his son Harris, Mary pieced together a parcel of land along
