Theodate Pope (left) and Mary Hillard at Miss Porter’s School, 1888. ARCHIVES, HILL-STEAD MUSEUM, FARMINGTON, CT.

      After Mary Hillard moved to Waterbury, she kept in touch with friends she had made in Farmington. One of them was Theodate Pope, a former pupil who was an unhappy only child from a wealthy Cleveland family. She did not get along with her conventional mother, questioning her lavish spending habits. In the fall of 1886, when the girl was almost twenty, her parents sent her to Miss Porter’s School instead of to Wellesley College because she was so poor in math. Theodate had been named Effie for an aunt, but the year she left home she renamed herself for a Quaker grandmother in Maine. At Miss Porter’s she struggled with her studies as well as her moods and was often depressed. She was troubled by finding more inspiration in paintings, books, music, and nature than in religion. She also agonized about whether it was her duty to live at home or marry or fulfill her dream of living on a farm with children adopted from poor families.

      Mary Hillard noticed Theodate’s depression and asked her to sit at her table in the dining room. Only four and a half years younger than the teacher, Theo, as she came to be called, was plain, short, sturdy, and broad-shouldered with light brown hair and expressive blue eyes. Feeling empathic toward the troubled girl, perhaps because of the mental illness in members of her own family, Miss Hillard recommended to her the inspirational words of the medieval monk Thomas à Kempis. Two months later, Theo noted in her diary that “Miss Hillard said that she thought there was nothing that could not be borne in this world, although borne perhaps with a struggle, except the consciousness of sin.” By spring the teacher and pupil had become close. “Miss Hillard made me promise I would come and see her when I feel blue and desperate. She is wonderfully nice to me. I have a walking day with her and I go every Sunday evening to see her.”

      The next school year, which would be Theo’s last year of education, the teacher tutored her in math while the girl developed a schoolgirl crush on her. Miss Hillard “knows everything,” Theo wrote in her diary. “She already knew something that I confessed to her today.” In March Theo’s parents withdrew her from school, supposedly because of illness, but the truth is that Mrs. Pope disapproved of Miss Hillard’s influence over her daughter, even bluntly telling the teacher to see less of the girl. During the summer a family friend’s eligible son, Harris Whittemore, proposed marriage to Theo, and the following year of 1888, the Popes departed for a year-long tour of Europe with the engaged couple. During the trip Theo confessed to her father that she didn’t love Harris enough to marry him, so the engagement was broken off, and the young man returned to America.

      Theodate had been making drawings of buildings since childhood. One day while the Popes were abroad, her father noticed her sketches of the farmhouse of her dreams and suggested that she study architecture. Although she now felt she had permission to lead a life different from her mother’s, she was still struggling with the strictures of upper class society. After the family’s return to Cleveland, Theo made her debut but soon afterward fell into such a deep depression that her parents sent her to a rest home in Philadelphia for a month. Perhaps on advice from a doctor, in May of 1890 the Popes allowed their daughter to rent a small eighteenth-century farmhouse in Farmington within walking distance of her former school. Over the next few years, rebelling against her privileged Victorian background, she restored the old farmhouse, which she named the O’Rourkery. Theo, who had become an ardent suffragette and socialist as well as a Unitarian, now wanted to become an architect. After studying privately with art and architectural historians at Princeton University, she began to design a home for her parents in Farmington with the assistance of the architectural firm of McKim, Mead and White. Finished in 1900, Hill-Stead was so impressive that writer Henry James, in his book The American Scene, likened it to George Washington’s Mount Vernon.

      After returning to Farmington, Theo was glad to renew her friendship with her former teacher. The Popes knew people who were part of the country’s intellectual and establishment elite, including writers Edith Wharton and Ida Tarbell, and even President Theodore Roosevelt. Over the years Mary Hillard would meet many of them at Hill-Stead, where she often went and spent many holidays, especially Christmas. She sometimes also stayed at the Popes’ suite in the Buckingham Hotel in New York City. As Mary and Theo became more intimate, they vacationed together, going to Bermuda in spring and to rustic camps in Maine and New Hampshire in summer, often with relatives and friends, including teachers at St. Margaret’s. Then in December of 1902, the headmistress of St. Margaret’s announced to her students that she was “rundown” and needed a long period of rest. A few months later, the friends sailed for Europe. It was around this time that Theo began thinking about designing a school for Mary, and they toured England and France with an eye toward what they most admired in architecture. The eventual design of Westover was influenced by the colleges in England and Europe where students both studied and lived. Spending a week in the guesthouse of an English convent and girls’ school, Mary was impressed by its chapel; she was also inspired by the cloister of the Salisbury Cathedral. In Paris they visited American artist Mary Cassatt, whose work the Popes collected. The friends also studied the French language along with the country’s history and literature at the Convent of the Soeurs de St. Augustin in Tours.

      In July of 1903, when the friends had been in Europe for six months, they heard from Alfred Pope, whom Mary now called Uncle Alfred, about new developments in the struggle for control over Miss Porter’s school after the headmistress’s death. Miss Porter had hoped that Mary Dow would be the new headmistress, and that Mary Hillard would be her associate and eventually succeed her, but the founder’s will had been challenged. When Mary heard the news, she 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