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Mary Hillard and Her Era:Protestant and Progressive

ON A DAY IN LATE APRIL OF 1909, A WOMAN NAMED THEODATE Pope and a group of teachers from St. Margaret’s School in the city of Waterbury, Connecticut, excitedly got into the Pope family’s chauffeured motor car, carrying a samovar, a ham, hatboxes, and precious colored photographs. The overloaded car made what one of the women later described as a “perilous” trip over the hilly six miles to the village of Middlebury. The village green, shaded by elms and encircled by white colonial homes and shops, was now bordered on one side by an enormous, pale stucco school with a steep slate roof and a bell tower. Over the large dark green door, an emblem on a projecting gable held three Tudor roses, a lamp of learning, and the commanding words “Cogitare, Agere, Esse” (or, “To Think, To Do, To Be”). A few days later, when a Waterbury newspaperman described the impressive neocolonial façade of the school called Westover, he noted that it would look better with shrubbery grown up around it.

After the teachers arrived, walked through the wide doorway, and looked around, they started to oversee the unpacking and arranging. At the end of the day, Lucy Pratt, Helen LaMonte and others happily settled down in a small front office and lit candles on its mantel and a fire in its grate. They waited for the new headmistress to arrive and “be delighted” by the sight, but when Mary Hillard finally rushed down the hall carrying her typewriter and papers, she was so busy that she didn’t even notice them. Since there was not yet any telephone or telegraph service to the village, it seemed as if they were far out in the country. When Miss LaMonte opened her eyes on the first morning, however, she joked: “‘Taint lonesome! Miss Pratt.’ So we began with gaiety—and it never was lonesome,” Lucy Pratt recalled forty years later.

The next day, the women continued to hurry around the huge, half empty edifice, unpacking blue Canton china for the dining room and endless boxes and crates. Theodate Pope locked the chapel door so no one would touch the drying varnish inside. “Workmen were underfoot everywhere, uncrating chapel chairs or putting turf in the Quad or carpet on Red Hall, but we somehow managed to go on in spite of all the activity,” recalled Helen LaMonte. Curious visitors were constantly arriving and asking to be shown around, she remembered, and her feet ached even though someone had thought to bring foot powder for everyone’s shoes.

Less than a week later, Miss Hillard and others stood inside the front door to greet the seventy or so pupils, who had formerly boarded at St. Margaret’s School, arriving after spring vacation on electric trolley cars from Waterbury. The young girls excitedly explored the many rooms as their trunks and more furniture slowly arrived up the hill by horse-drawn wagons, a procession that was halted for a few days by a spring snowstorm. As the unpacking paused, Lucy Pratt took the time to write to Theodate Pope, who had left for a vacation in Cuba to rest from her exhausting preparations as the school’s architect. “We have been in our beautiful home one week … [and we think] with love of our blessed architect … for every peg in every closet, every latch of every door, every screw in its place sings Theodate. My sweet bedroom almost keeps me awake with the peace of its beauty.”

In the middle of May, the three apple trees inside the inner courtyard put forth arrays of pale pink blossoms as one of the loveliest springs in memory got underway. Amid the excitement there were a few emergencies. A girl suddenly needed an appendectomy, and without a motor car available to get her to a hospital, the operation was performed on ironing boards in the unfinished infirmary. Someone threw a few muslin blouses, called waists at the time, down a chute labeled “waste.” Then the well water ran out. Nonetheless, Mary Hillard was elated. “We are in! It is all so beautiful and good,” she wrote to a friend in late May. “It is all so good a start,” she added a few weeks later. “A beautiful spirit was here, that matched our beautiful setting, and I think our life had a benediction in the sweetness and consideration that my dear girls showed through the days of adjustment, and that every helper, from the servants up, seemed full of. So that I shall always look back to those days of real stress with such deep thankfulness as being full of something living and spiritual.” When the school term ended in June, the twenty seniors returned to Waterbury for a graduation ceremony with their former classmates at St. Margaret’s School, mostly day students who lived in the bustling city.

BY THE TIME WESTOVER OPENED, the task of educating girls already had a long and contentious history. In 1792 during the Enlightenment, eighteenth-century English feminist Mary Wollstonecraft had called for their equal education with boys. In Thoughts on the Education of Daughters, she urged mothers to teach their daughters so they would learn to think, and she herself started several schools for girls. Early on in New England, there had been dame schools, where young children were taught to read, write, and do arithmetic in the homes of women. After the American Revolution, it was regarded as patriotic to educate the future “mothers of the republic,” those who would educate the male citizens of the young democracy. Connecticut had enlightened attitudes about educating females, and many of the best schools for girls were in the state. One was Sarah Pierce’s school in Litchfield, which opened in 1790 to educate the daughters of merchants, landowners, and ministers, including educator Catharine Beecher and her sister, author Harriet Beecher Stowe. Because of the difficulty and expense of travel at the time, they were by necessity boarding schools. In the nineteenth century, a new generation of female educators urged women to take responsibility for educating members of their own sex, and one of them named Emma Willard briefly ran a female seminary in the village of Middlebury.

The school called Westover was Mary Hillard’s idea long before it was anyone else’s. She envisioned it as a wholesome setting for study and sports, as well as a school in which to instill in young women useful knowledge and idealistic values. It was as if she were trying to recreate the most ideal conditions of her own childhood. Born and raised in Connecticut villages like Middlebury, she knew them intimately as places where a traditional way of life went on apart from all the rapid changes going on in America. This was particularly true of Plymouth, where she lived during the impressionable ages of seven to seventeen with her family in a parsonage on a hill above the Naugatuck River valley in central Connecticut, where brass factories were attracting thousands of immigrants from southern Europe.

The Rev. Elias Brewster Hillard was the minister of the big white First Congregational Church of Plymouth. A member of the New England intelligentsia, he had acquired a fine education at Andover Academy and Yale University, where he graduated with the class of 1848. His thinking was liberal, learned, and open-minded, particularly about the education of his daughters. He was also curious, candid, excitable, and courageous; even as an old man he had “vividness and aliveness,” remembered his grandson, poet Archibald MacLeish. The minister liked to tell his children stories about their ancestors, Puritans who had sailed from England in the early 1600s. There was the tale of great-grandparents captured by Indians, and one about their grandfather Moses, an enterprising ship’s captain who attempted to smuggle Napoleon out of France. In his spare time Elias wrote a book about four forgotten Connecticut heroes of the American Revolution.

When the young minister was the principal of a private school in Southington, Connecticut, he met his future wife, Julia Whittlesey, a student there. The daughter of a Yale-educated judge who had moved to Cleveland, Ohio, Julia was sent back East to finish her schooling, and she received what was considered the best possible education for a female in her day. Julia was diminutive and delicate with big, bright, brown eyes and dark hair. Besides being very feminine and lovely looking, she was possessed of a “sweet selflessness” and “charm and inward grace,” according to this grandson. When she became the mother of a large family, she was also firm, frugal, humorous, and extremely organized. Despite her practical nature, she also had an interest in spiritualism. The couple was well matched. “I can see Elias flying off on tangents and Julia holding onto his coat-tails,” said Mary Robbins Whittlesey, Julia’s older sister, for whom her daughter Mary was named.

The couple’s eldest child, Martha, born in 1856, went to Vassar College, which had opened its doors when she was nine. Her college tuition was paid for by the estate of a tall, aristocratic, and emotionally disturbed aunt who lived with the Hillards, a woman who suffered from what was called “insanity of the will.” After teaching mathematics at Vassar, Martha became principle of Rockford Seminary in Illinois until she married Andrew MacLeish. A leader in progressive education, social reform, and missionary work, she helped Jane Addams establish Hull House and was president of the Chicago Women’s Club, among many other activities. Frederick, born a year later, would invent typewriter parts but fail to profit from his patents. The third child, Helen, became a nurse and was a founder of a settlement house. Mary was born three years later in the summer of 1862, and the petite Emily was born four years after that. Then there was Fanny, who was mentally ill most of her life. The next child, precocious and sickly William, died at the age of twenty. Another son, Arthur, lived only a year. The youngest and ninth child was John, born when Mary was a teenager, who became almost like a son to her.

The Hillards raised their children based on the theories in Horace Bushnell’s Christian Nurture, which was a more affectionate approach to childrearing than the strict Puritan way; years later, however, when a young man remarked to Mary that “one hardly dares to be too happy,” she asked him with surprise, “have you got that in your background, too?” Martha later portrayed the Hillards as a happy, if financially strapped, family. Their religious expression was “simple, sincere, and beautiful,” and the children were instilled with the highest ideals. Mary was especially idealistic and wanted to become a missionary in China. In the evenings their father would read aloud Dickens, Stowe, and other novelists, while Julia and their daughters would sit around a large table doing needlework. Elias also enjoyed taking his children picnicking and camping. When he went about his parish in a sleigh or horse and buggy, he liked to take young Mary with him; she later said that she had noticed and remembered everything, like the differences in intellect and personality among his parishioners.

The Hillard family around 1894. From left: Emily, Martha (Ishbel MacLeish in lap), Elias Brewster Hillard, Mary, John, Helen, Archibald MacLeish, Julia Whittlesey Hillard, Frederick, and Fanny. CONNECTICUT HISTORICAL SOCIETY.

At the time Mary was born, on June 14, 1862, in the Connecticut village of Kensington, her father was deeply upset by the outbreak of the Civil War the year before. Inheriting her mother’s dark eyes, she would also acquire, in her eldest sister’s opinion, her mother’s take-charge manner, sense of spirituality, gift for organization, and strong belief in right and wrong. When she was a teenager, a classmate described her as “very tall, angular, almost ungainly … [but with a] directness, a dashing quickness of motion, [an] entire absence of self-consciousness and great dignity … Plain of face she may have been, dark olive and even sallow in coloring, but a face which lighted up radiantly and which was redeemed by the deep-set, very dark, very penetrating eyes—sympathetic often, quizzical oftener and with a look so far away at times that she was even then thought quite mystic and unsearchable.” This classmate, Martha Coffin, also went on to say that “there was infinite pathos” in Mary’s eyes, orbs that “were always darkened by deep circling shadows”; some friends even “called her sad-eyed.” The classmate also remembered “the fine modeling of the head, that something quite lovely about the brow and temples.” Mary grew to be one of the tallest members of her family as well as the most attractive of the clan, according to a family photograph taken around 1894, when she was thirty-two. In this photograph she is the most stylishly dressed among her dark-garbed parents and siblings, wearing a handsome light-colored suit and a dark high-necked blouse. Sitting near the center of the group, she exudes such a strong force of personality that she eclipses everyone else, even her brilliant older sisters.

After attending the local schoolhouse in Plymouth, Mary followed her sister Helen to the Collegiate Institute for Young Ladies in Waterbury, a school run by the Episcopal Church and renamed St. Margaret’s School for Girls when Mary was thirteen. Uncle Moses Hillard, a bachelor, helped with the tuition. When the headmaster of St. Margaret’s, the Rev. Francis Thayer Russell, realized that high-spirited Mary was not settling down to study, he suggested to her parents that she might do better elsewhere. At the age of eighteen her parents enrolled her in Abbott Academy, a girl’s school on a hill in Andover, Massachusetts, where she came under the influence of the elderly, authoritative headmistress, Philena McKeen, a husky-voiced woman with ringlets on both sides of her face. Mary was expected to earn her tuition, so she ran the supply shop and led a gymnastics class. She admired Miss McKeen, and a number of her later educational practices—quiet Sabbaths and simplicity of dress—became traditions at Westover. In her studies, Mary was fair in algebra and Latin but poor in French and German as well as in music and drawing. What interested her intensely were the ideas inherent in the study of history: the history of art, the history of religion, the history of linguistics, and the history of England. She also read voraciously on her own, as she would do all her life.

From an early age she was exceptional in her gift for public speaking. When asked to recite in class, she would turn recitation into something else, “a thought and question-provoking forum,” in the words of Martha Coffin. A natural leader, she was regarded as the head of the school even before she was elected president of her class. She was also firm and opinionated. Girls who went to her for advice often got “a strong bracing up, a sound whacking” instead of sympathy, recalled this classmate, who noted that nothing dampened her high spirits. One of her friends summed her up as “the biggest tease, the one who always kept her things in perfect order, who always had time for any fun going on (mostly setting it going), made the best use of her time, worked the hardest, and had the best time of any girl in school.”

The Rev. Hillard supposedly wanted Mary to go to college like her older sisters but, for reasons that are not entirely evident, she did not wish to go. Perhaps she realized that she was not a scholar, or her certainty and independence made college appear unnecessary. In an era when differences between academies and universities were not as distinct as they are today, she stayed at Abbott for four years, until she earned her high school diploma around the time of her twenty-second birthday. On graduation day she gave an impressive valedictory speech and then returned home to teach children in the Plymouth schoolhouse.

A year later, in 1885, Sarah Porter hired her to teach at her long-established girls’ school in the village of Farmington, a few miles west of Hartford. It was to Mary Hillard’s advantage that when Miss Porter hired a teacher, she was less interested in her education than in her character—“a clear and well-trained mind, quick sympathies and a pure heart” were what she wanted. Perhaps the headmistress at the age of seventy-two saw the twenty-three-year-old Mary as a younger version of herself; both were descendents of old American families and daughters of Congregationalist ministers. There were some differences, however: Sarah Porter, whose brother was the president of Yale University when she hired the young teacher, was a scholar who had studied languages and other subjects with Yale professors throughout her life. A pious woman who dressed in handsome black dresses in winter and gray ones in summer, she was also a person who valued simplicity and humility and was supposedly indifferent to the social backgrounds of her wealthy pupils, preaching that “wealth did not make worth.”

Young Mary Hillard was deeply impressed by this woman, who became a mentor. She admired the way the older woman impressed old-fashioned values upon her pupils to prepare them for family life rather than for teaching, missionary, and other kinds of women’s work. Yet unlike traditionalists who believed that the female body did not have enough blood to sustain both the brain and the womb, Miss Porter also rejected the idea that mental activity undermines a woman’s family responsibilities, and she attempted to prepare girls for lifelong intellectual and spiritual growth. Mary Hillard later said that she was very grateful to Sarah Porter for teaching her everything she knew about successfully running a school during the six years under her wing.

Those years of her early twenties were the time when the lovely Mary Hillard would have been most likely to marry. An old friend of hers acknowledged that Mary had been in love as a young girl, and that she had struggled “to decide between love and duty.” Teaching evidently tapped her idealism: the little girl who had wanted to be a missionary in China now wanted to enlighten and lead young women. If she married, she knew that she would eventually have to give up teaching; wives almost always left or lost their jobs especially after the arrival of children. At that time she expressed caution about romantic feelings. Miss Hillard has “some queer ideas, such as that a girl should never love a man before he asks her to and then she cannot be certain whether she can care for him or not but must wait to find out,” confided Elizabeth Failing, a Miss Porter’s pupil, to her diary. Miss Porter viewed romantic infatuation as a feeling to be directed toward the good of the family, a view the young teacher would also articulate. At the Westover graduation of 1917, she declared that marriage is not for personal happiness but a way to pass along values to the next generation.

Even at that early age, Mary Hillard had a knack for understanding girls; Elizabeth Failing also wrote in her diary that she was in awe of her teacher’s insight into her at a party where Miss Hillard told fortunes and placed an apt quote about each girl at her plate. The girl also wrote about her admiration for her energetic and entertaining young teacher: Miss Hillard is, she wrote, “like a breeze [that] stirs up the air and implants a new vitality.” Still, Mary Hillard came to regard herself as less gifted as a teacher in the classroom than as a leader who could inspire young women with her melodic speaking voice. Miss Porter noticed her leadership qualities and soon gave the youthful teacher a small administrative role in one of the school’s dormitories.

Mary Robbins Hillard as a young woman. L. ALTMAN & CO.

By that time Miss Porter had already chosen her successor, assistant principal Mary Dunning Dow, a former pupil and a widow who was much older than Mary. At the same time, the scholarly and elderly headmaster of St. Margaret’s School in Waterbury was looking for an assistant. His wife had recently died, and one day during a visit with a parishioner he confessed his difficulty in trying to run the girls’ school alone. The woman, whose daughter had roomed with Mary Hillard at St. Margaret’s, mentioned the young teacher as someone with energy and ideas; one thing led to another, and Dr. Russell offered Mary Hillard—whom he had asked to leave the school some fifteen years earlier—the position of assistant principal. When she told Miss Porter about the offer, the older woman urged her to take it, telling her that she had a talent for leadership. Mary’s reservations were about leaving the peaceful village of Farmington for the busy city of Waterbury. Also, she had enlarged her circle of friends in Farmington to include more sophisticated people than those in the parsonages of her youth. Miss Porter assured her that she would find similar people in Waterbury, like the fine old New England family of Edith and Frederick Kingsbury, who had two daughters her age living at home. As Mary Hillard turned twenty-nine, she decided to go.

As Miss Mary Hillard walked rapidly through the streets of Waterbury in the autumn of 1891, she carried herself with more dignity and solemnity than usual, aware that she was being observed. A tall, slender, single woman with searching eyes, she was remembered for parting her long, dark brown hair in the middle and pulling it back into a knot at the back of her head. Instead of elaborate Victorian fashions, she wore the more practical clothing of the professional women of her day. “There was an air of austerity mingled with something athletic,” an observer recalled. “The shirtwaist with a collar and bow tie, the longish skirt, the absence of anything colorful, the modest hat, gloves, all bespoke restraint.” She brought a pearl-handled knife to St. John’s Episcopal Church in the city, where St. Margaret’s trustees and most of its pupils worshipped, to cut tight corset strings of girls who fainted during services. Although young men were awed by her, she got to know several Yale graduates who worked for The Waterbury American as well as families who knew her father. Direct and businesslike, she gave people the impression that she knew what she wanted and had no time to waste. “There were inner fires always burning in her,” observed a younger friend, the Rev. John T. Dallas, assistant pastor at St. John’s, who would get to know her very well.

Her sense of urgency was undoubtedly exacerbated by the realization that St. Margaret’s was in debt and in decline. She had quickly discovered problems with the school’s faltering furnaces and its drafty, dilapidated Victorian wooden structure. About a year after her arrival, Dr. Russell became ill, entered a New York City hospital, and sent in his resignation. The board of trustees asked Mary to take his job. In an act of astonishing audacity by a woman barely over the age of thirty, she said no. Instead, she responded with a counteroffer in which she proposed to rent the rambling building from the trustees and run St. Margaret’s as her own school. As gestures to reassure the trustees, she offered to hire Dr. Russell, who had remained in New York to teach theology, as rector and to meet with them once a year.

Mary Hillard obviously did not want to be under the thumb of older, more cautious male trustees who, she feared, might not be willing to borrow enough money to turn the school around. She felt supremely confident that any debts she took on would be eventually repaid as she increased enrollment. The trustees, including Frederick Kingsbury, must have been taken aback by the demands of the young woman, but by 1894 they agreed to them. Kingsbury, whose mother had gone to Miss Pierce’s School in Litchfield, was a firm believer in women’s education and most likely in women educators as well. The young headmistress was equally persuasive with Waterbury bankers. At the end of every school year, when tuition income ended and teachers had to be paid and repairs undertaken, she would take out a personal bank loan endorsed by Dr. Russell simply on the strength of a handshake.

It was during this time in the late 1890s when she began to hire the teachers a few years younger than herself who would follow her to Westover and be lifelong friends. She asked Helen Dean LaMonte, a member of the Smith College class of 1885, to teach art history and literature. Lucy Bailey Pratt, a teachers’ college graduate, took charge of the kindergarten. She also hired Henriette Coffin, a young Frenchwoman, to teach the French language and literature, and Helen Andrews, an artist, to teach drawing and painting. In 1900 her younger sister, Fanny, was teaching psychology and history at the school, but she, like their oldest sister Martha, gave up teaching when she married. During the first decade of her sixteen years at St. Margaret’s, Mary borrowed and repaid huge amounts of money for repairs and, with the help of a gift in 1902, finally got the school out of the red. Meanwhile, enrollment increased so much that she had to rent a house near the school for all the new boarders.

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 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 the south side of the Middlebury green that soon amounted to twenty-five acres. Involved in all the legal and financial details, she was so able that one of the shareholders, banker James S. Elton, said he regretted that because she was a woman she could not be president of the Waterbury National Bank. Mary wrote Harris Whittemore that she was “on fire” about her school, and when someone declined to buy stock, she would simply ask again. In 1907 Theo’s architectural plans were finished and Richard F. Jones of Hartford, a contractor who had built Hill-Stead and also worked for the Whittemores, was chosen. John Whittemore signed the construction contract in September, but before building could begin it was necessary to move the Methodist meetinghouse and its parsonage, the Middlebury general store and post office, a blacksmith shop, a clapboard farmhouse, and several towering elms. All but three apple trees in an old orchard were cut down, and the soggy pastures of a farm were filled to become playing fields.

Westover School under construction about 1908. WESTOVER SCHOOL ARCHIVE.

When word finally got out about the plans, there was an uproar. It was feared that the trustees as well as the principal were abandoning St. Margaret’s. At a meeting in November, alumnae and others presented two petitions protesting the loss of the boarders to trustee Chauncey B. Brewster, the bishop of Connecticut, but by then most trustees were already backers if not stockholders of “Mary’s school.” Finally Miss Hillard was forced to publicly explain. In a lengthy letter to The Waterbury American, she complained about being misquoted and misunderstood and heatedly defended herself and her plan for a new school. She wrote that she felt “naturally” entitled to take boarders and teachers with her to Middlebury because it was she who had attracted them to St. Margaret’s in the first place. She explained that prospective parents of out-of-town pupils worried about their daughters’ lack of athletics and “freedom of life” in Waterbury. The handwriting on the wall became clear, she went on, when her “own old girls” began urging her to do something so that they could send “their daughters to me” to be educated. She also pointed out that without boarders at St. Margaret’s, there would be more room for the Waterbury girls. Finally, she added that the pupils at the new school would continue to patronize Waterbury churches, concerts, hotels, and businesses. The storm blew over, but a newspaperman wrote sarcastically that the young ladies will go to Middlebury, “where the bloom of the cowslips is unpolluted and the rarified atmosphere untainted with the soot of industrial progress.”

This ivory tower had been estimated to cost a quarter of a million dollars, but by the time it was finished it would be more than twice that amount. Although Theo designed the building without a fee, she never felt constrained by a budget. As expenses mounted, more stock was issued; then in late 1908 when a large amount of money had to be borrowed, Mary refused to agree to the loan until the stockholders had taken out an insurance policy on her life and until dividend payments had begun. (Afterward Mr. Whittemore admitted to her that he had never believed dividends would ever be earned, and he was surprised and pleased to be wrong.)

As construction got underway, the Pope’s chauffeur drove Mary and Theo to Middlebury almost every day. One moonlit evening when the two women went to Middlebury to inspect the new foundation, Mary felt overwhelmed by its size—it was a hundred and twenty-five feet square—so Theo calmed her by telling her to let her “spirit” fill the space. After the walls went up, stucco was applied, made of white sea sand, goats’ hair, and lime, supposedly a formula that Michelangelo had used for frescoes. They envisioned the large interior of the four-sided structure with its covered walkway as a place for walking in bad weather. “This quadrangle is filled with sunshine falling over the low roofs,” Mary wrote in the first school catalog. “The spring sunshine in these sheltered conditions will bring bulbs and shrubs into early bloom.” She was more than pleased. And after telling Mr. Whittemore that the building of the school was going “very well,” she added: “I took advantage of the fine sleighing and a beautiful day to take the schoolgirls out to see it. They could talk of nothing else for some time they were so charmed with it all, the location, the building, the New England green and all. It had just the effect I knew it would have upon them, and they are already planning coasting and skating and all the sports. There was but one dissenting voice among them. ‘But where is a corner grocery for getting olives and crackers?’ said one mournful fifteen year old, little knowing that one of my joys is the absence of corner groceries and soda fountains!”

Nicknamed “the Nomadic Queen” by the Rev. John N. Lewis, Jr., of St. John’s Episcopal Church in Waterbury, Mary Hillard ended up taking almost all the St. Margaret’s boarders with her to the new school like a pied piper, leaving only six girls behind with the day pupils. The teachers, maid, and handyman who followed her to Middlebury were those who were devoted to her. Many times throughout her life she would say that after loyalty to “Truth, Justice, Patience, Courage” and other ideals, she believed in loyalty to people. Most of them stayed for the rest of their working lives at the school called Westover, which was given its name because it was west and over the hill from Waterbury.