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The Art of Living:A Balanced Life


MARY HILLARD HAD ALWAYS WANTED HER SCHOOL TO BE A place devoted to the wholesome values of her girlhood, the same ones that had shaped the grandmothers of most of her pupils. Life at Westover would be “simple, sincere, and natural,” she had written in the school’s first catalog. Her own childhood had consisted of “an education which brought her soul in touch with God, her mind in contact with the great thinkers of the past and present, [and] her body in contact with nature in all her aspects among the hills of Connecticut,” in the words of a her minister friend in Waterbury, John Dallas. As she structured a way of life for her young charges—one she envisioned as a balanced existence—she hoped that they would adopt it as their own after graduation. Some activities and traditions were similar to those in other girls’ schools, and others were unique to Westover. Mornings were for classes, afternoons were for exercise, and evenings were for studying in the schoolroom, or dancing in the gym, or attending events in Red Hall, or listening to the headmistress read aloud in her sitting room.

The first Westover yearbook, for the 1911–1912 school year, indicates the way the days made up a routine, marked by traditions, in a rhythm that would be repeated for years. On many Saturday nights there were “germans” (a word meaning little plays), parties with songs, favors, costumes, and skits put on by the seniors, athletic teams, and others. From the first year there was the performance of a nativity play in the style of an old English pageant before Christmas vacation. Early on Easter mornings the seniors surprised the new girls by awakening them while walking down their bedroom corridors singing hymns. For a few years there was also a May Day dance with a queen and maidens, along with singing, dancing, and the winding of a Maypole.

As always, there was the emphasis on building strength of character. Echoing Mary Wollstonecraft, an early Westover catalog stated that the goal of academic work was to train the mind to reason and to control the emotions. The importance of thought was underscored by the motto on everyone’s brass belt buckle, “To Think, To Do, To Be.” Learning, Miss Hillard believed, should also stimulate originality and inventiveness: “A person of liberal education should radiate life and joy and color by passing everything through the prism of the imagination,” she liked to say. Freshman year studies were intended to develop concentration, while subsequent years were planned to inform and train pupils’ tastes in art and literature. All this education reached an epitome in the senior year. “The studies of the Senior Year, which the thirty odd other lovely girls who will make up our Senior Class next year are to have, are of an especially cultivating character,” Miss Hillard wrote persuasively to the mother of a prospective student who had spent the previous year in Europe.

Besides offering classes in art and literature, the school had many others in European and American history as well as a few in psychology, mathematics, astronomy, geology, physiology, and botany. The learning of languages, including Latin and Greek, was stressed, and plays were performed in German and French. Although the headmistress did not emphasize academics to the exclusion of everything else, she did, unlike Sarah Porter, put pressure on pupils by ranking them academically and reading aloud the list from highest to lowest on a day that was dubbed “Black Monday,” a practice modeled on boys’ schools. She also scolded poor performers. When freshman Marianna Talbott got the lowest grades in the school, Miss Hillard “gave me plain hell in front of the whole school,” the girl wrote in her diary. To encourage good grades, the principal established a policy that allowed a new girl who got over ninety in every lesson in a week to read in the library instead of going to study hall in the evenings.


Mary Hillard (left), Helen LaMonte, and Lucy Pratt. WESTOVER SCHOOL ARCHIVE.

Many graduates spoke glowingly all their lives about the brilliant teaching of Helen LaMonte, who was born the youngest of five children in 1872 on a farm in Owego, New York. It was the quality of her intellect that impressed them as much as her extensive knowledge. In her History of Painting class, which she taught in a large wood-paneled room, she asked pupils to research paintings and then paste reproductions of them in notebooks. “She was a magnificent teacher,” recalled a former student, who credited her with all she knew about art. Many others never forgot what she had said about particular paintings, and when they got to the Louvre and the other museums in Europe (sometimes with their notebooks in tow), they headed for those works of art. Miss LaMonte also taught Literature of the Nineteenth Century, the study of English prose and poetry. One alumna remembered thinking as she entered the class that “‘this is going to be good’—and it always was.” Not only was the teacher’s imagination a delight, but she also explained poems clearly. Another graduate, who wanted to stay at Westover until she had taken every course that Miss LaMonte taught, recalled gratefully that “it was she who opened my eyes to art and my ears and mind to poetry and literature.”

Part of a well-rounded life, in Mary Hillard’s opinion, was to experience the beauty of nature. Early on she had bought seventy acres and a small nineteenth-century farmhouse in the nearby village of Woodbury. While there is evidence that she acquired the property by borrowing money from friends, she had long believed that principals of profitable schools have the right “to share liberally in the earnings of the school,” and she apparently earned an excellent salary. The farm was her personal retreat as well as what she called “a holiday house” for student picnics, parties, and overnight stays with teachers and without any help from maids. She had adored picnics ever since her father had taken his children picnicking, and as headmistress she organized outings often at the farm, where everyone, herself included, cooked outdoors, cleaned up, and sometimes played baseball, and then took the trolley or walked through the woods at night back to Middlebury.

One of the most enthusiastic people about the outdoors was Lucy Pratt, a redhead with a plain face and a prominent nose, who loved the long walk from Middlebury, past Lake Quassapaug, to Woodbury and back. She also liked to lead girls on back roads all the way to St. John’s Church in Waterbury for services on Sunday mornings. Along with art teacher Helen Andrews, a quiet painter and etcher who had studied art in New York and Paris, she loved searching for and spreading the seeds of wildflowers they discovered in the woods. Trained as an elementary school teacher, she also loved to give parties for village children in the little white clapboard house near the Methodist meeting house, which the youngsters liked so much that they called it “paradise.” Miss Pratt, who worked at a standup desk in a little downstairs office with a fireplace, was responsible for business matters, housekeeping, and upkeep of the grounds. She was so soft-spoken and kindly toward the maids and maintenance men that they nicknamed her St. Lucy. Among the threesome who ran the school, it was she who was eminently practical and meticulous about details, and over the years she was school secretary, treasurer, and an assistant headmistress.

A self-effacing person from a large New England family, Lucy Pratt was also down-to-earth and possessed of a lively sense of humor, a firm ethical nature, and a strong dislike of pomposity. Like Helen LaMonte, she was devoted to Mary Hillard, but she could also deflate the headmistress when necessary, like the time she jokingly referring to her as “the Wise Woman” in a letter to Theodate Pope. When a girl was in danger of being expelled, Miss Pratt believed that if she would admit her mistake in breaking a rule she could stay, but if she would not or was untrustworthy, then she had no place at Westover. She was also dauntless: once when some seniors spotted a Peeping Tom outside the schoolroom, it was she who got into an automobile (along with, according to a rumor among the students, three men with pistols) to chase him away.

Exercise was an important part of a wholesome life, in Mary Hillard’s view, and an important reason for a school to be in the countryside. After a childhood of outdoor activities, she was convinced that young ladies suffered from too little exertion. The need for physical education for women was a relatively new idea at the time, and she was one of its ardent defenders. During Westover’s first year, girls were divided into athletic teams—Wests, Overs, and Seniors—for tennis, field hockey, and basketball games, and the three apple trees within the quadrangle were named for each team. The headmistress herself selected who would be Wests or Overs and read off the names in the dining room at the beginning of each year. Also, girls were encouraged to take cross-country walks or jogs for three or four miles in groups of at least four. In the winter there was tobogganing, snowshoeing, and ice skating on the school’s pond. For an extra fee girls could go horseback riding.

Miss Hillard had a way of getting girls to both go outside and learn poems by heart. If a girl failed to exercise and cross her name off what was called “the walking list,” she might be called on to recite at dinnertime the poem that everyone had to memorize each week. The poems were by Emily Dickinson and Emily Brontë as well as by Milton, Yeats, Tennyson, Blake, Stevenson, Keats, and by living poets who gave readings at the school like John Masefield and Walter de la Mare. On beautiful spring days, Miss Hillard, who adored poetry, might take English classes outside and read poetry to them as they sat on the grass. On other days she might suddenly appear in the schoolroom, put on her pince-nez spectacles, read a poem by Shelley or Wordsworth, and then quietly leave. The threat of being asked to recite a poem aloud, however, was a penalty that made some girls resent poetry and even dislike public speaking for the rest of their lives.

The first issue of The Lantern noted that a balanced way of life was not one of “solemn priggishness” but one that also “smacks of fun” for students and adults alike. For a Halloween german, Mary Hillard dressed up in a school uniform and a mask and passed around a box of chocolates until the girls realized who the tall, mysterious figure really was. At least once Lucy Pratt dressed up like an opera singer and sang an aria, while Helen LaMonte accompanied her on a violin. Julia Whittemore, the widow of John H. Whittemore, used to invite the seniors to a picnic with lobsters every autumn. On winter nights, all the girls were from time to time loaded onto seven or eight sleighs pulled by horses with bells in their harnesses for moonlit rides and hot chocolate afterward. One spring evening early on, the hockey field was illuminated with lanterns while girls danced minuets. Throughout the years there were many teas and dinners and birthday parties at the little cottage near the school called Crossways. When seniors in the class of 1919 got up their courage to invite Miss Hillard to dinner there, their dignified headmistress surprised them by being “very affable,” one of them recalled. There was also what was called the tea bureau on Saturday afternoons in the rented basement of the Methodist meeting house, where girls played the Victrola and sold tea, hot chocolate, and little cakes to earn money for charity.

Social events with young men were also part of a well-balanced life. Girls regularly went in chaperoned groups to the Yale-Harvard and Yale-Princeton football games. There were teas and dances with the students of Taft School, a boys’ preparatory school only six miles away in Watertown. Taft’s headmaster, Horace D. Taft, was a very tall, warm, quiet man and a good friend of Miss Hillard’s. He had become a widower the year Westover opened its doors, and, although girls liked to imagine that there was a romance between the two of them, Mr. Taft had vowed never to marry again. There were also dances at Westover, and the headmistress gave a dancing prize of a Tiffany clock to the escort of a member of the class of 1910. Even though her girls wanted to learn the latest dances, it’s unclear what kind of dancing took place since waltzing had shocked Mary Hillard as a child, and in adulthood she was still opposed to what she called “contact dancing.”

By that time Mary Hillard was an impressive woman in her fifties with poise and power, a person who wore handsome day dresses and lovely dinner gowns, many made in Paris. Her usual daytime outfit was a well-tailored dark blue suit or dress of heavy navy silk with an organdy collar or other trim. Her dresses were often made in the same patterns and with a ruffle below the waist covering a pocket for a handkerchief. Graduates never forgot her evening gowns of pale gray chiffon, of white Swiss polka dots with an embroidered square collar, and many others. Some always remembered her beautiful shoes with silver buckles. In 1918, after years of raising money, her portrait was painted by the acclaimed portraitist of the American upper class, Lydia Field Emmet, who was a friend of Theodate Pope’s. The artist, who had studied with the famous William Merritt Chase, came from a family of accomplished women painters. In the large portrait, the founder’s dark eyes look out from under graying hair in an unusually pensive way. And instead of wearing one of her elegant gowns, she posed in the black academic robe she had received the previous year when awarded a Doctor of Humane Letters from the University of Vermont.

Over the years, Mary Hillard spoke about spiritual values so often that it was as if she were a minister or a missionary instead of an educator. There could be no balance in a life without them, she fervently believed, and she felt that her greatest responsibility was to instill religious ideals in younger generations. “True schools are not founded on theories of education,” she liked to say. In fact, like earlier women educators—Sarah Pierce, Catharine Beecher, Emma Willard, Sarah Porter, and others—she was a believer in moral education. “Without this there may be training of mind and development of aptitudes but no true education,” she remarked at more than one Westover graduation. In this way she sounded like a disciple of Thomas à Kempis, whose work she knew well. “Intellectuals like to appear learned and be called wise,” he wrote in Imitation of Christ. “Yet there are many things the knowledge of which does little or no good to the soul.” She also said on many occasions that the essence of an education at her school was learning about what she called the “Everlasting Reality—of Truth, Justice, Love, Mercy, Honor, Pity, Courage.” She would go on to explain that “it is the aim of this school to develop this combination of imagination, disciplined will, and effective power of resolution” by exposing young girls to religion as well as to literature, art, music, and what she simply called “beauty.”

As the headmistress devoted herself to her pupils’ spiritual development, it was evident to her and to everyone else that she understood adolescents very well. Little eluded her. As girls walked into the dining room for breakfast two by two, she stood at the doorway and looked them over intently. If she let a girl pass, the girl felt reassured; if she noticed that someone looked disheveled, tired, or troubled, she would call her aside and talk with her. This happened a few times with Polly Willcox, a member of the class of 1918. The only daughter in a close-knit family in Ithaca, New York, she felt “exiled from heaven” after she first arrived in Middlebury during World War I, a feeling exacerbated by entering in the middle of the school year after her classmates had already made friends. When Miss Hillard took Polly aside, she comforted her by saying, in effect, “don’t ever forget that I’m here,” and by reassuring her that she would get over her homesickness. Their talks made the girl feel special, safe, and secure because the headmistress “recognized my need,” as she remembered more than eight decades later, when she was a hundred years old.

Polly Willcox also described Miss Hillard’s manner as one of “formality over deep empathy.” She elaborated: “She drew people to her in spite of her formality. There was no feeling of forbiddingness. She was very open and warm. And extremely perceptive. You felt transparent in her view.” The headmistress’s insight was a trait that was also noticed by pupils at Miss Porter’s in the 1880s, as well as by members of the last graduating class she knew at Westover in the early 1930s. When she stood outside the chapel after evening vespers services to say good night to each pupil, every girl felt as if she was looking right through them. (Some teenagers found this so disconcerting that they tried to make their minds blank when they walked by.) Polly went on: “So many of her talks and lectures were so helpful. They made you realize what was the right thing to do and always put you on the right track.”

Many girls found that being away from home was a way to discover themselves. An editor of The Lantern wrote in 1924 that the purpose of boarding school was to find where one’s abilities lay—whether they were intellectual, athletic, artistic, or as leaders—and to develop them, with the effort being more important than the achievement. As their headmistress created an enriched environment by continually quoting Heraclites, Aristotle, Plato, Moses, and Shakespeare, as well as theologians, poets, and novelists, pupils also felt that they were part of something greater than themselves. Life at Westover had a feeling of “great dignity,” in the words of Polly Willcox. It was “formidable, imposing, benign, friendly, supportive,” she added. “I think it was a splendid school, and I loved it very much after the first year.” (Not everyone had her attitude and adaptability, however, and a classmate, who stayed only one year, disliked the aura of “Victorian sentimentality that made me not only figuratively but actually sick.”)

There was nothing unintentional about what Mary Hillard was trying to do: she wanted the young girls placed under her wing to mature emotionally. She talked again and again about the need for them to develop what she called spontaneity—the ability of a teenager to shed self-consciousness and to become herself. It was the way French diplomat Alexis de Tocqueville had described the surprisingly frank voice of the American girl in the 1830s: she “has scarcely ceased to be a child when she already thinks for herself, speaks with freedom, and acts on her own impulse,” he wrote in Democracy in America. The headmistress believed it was a matter of reawakening an earlier naturalness before inhibition set in, the same phenomenon among adolescent girls that Harvard psychologist Carol Gilligan would describe many decades later in her book In a Different Voice. It was, in fact, a pivotal part of Mary Hillard’s educational philosophy that adults should create the conditions for youths to heal and, in other words, “to be trained by us to be free.” This process of personality development could only happen in a small caring community like Westover, she believed, a place that celebrated familiar traditions and provided new experiences.

Among the girls the headmistress understood very well was her niece, Phyllis Fenn, the daughter of her younger sister Emily. Aunt Mary had “many times been the guardian angel of the family,” according to their older sister, Martha, by taking a strong interest in Phyllis and in Martha’s daughter, Ishbel MacLeish, as well as in her numerous nephews. After Phyllis’s first year at Westover in 1920, however, her mother wrote a worried letter to her sister saying that her only child was no longer lighthearted. In her reply, Mary said that at school Phyllis was “bubbling over with interests and fun,” and that it was a “tremendous” transition to go from school to home in the summer. She also elaborated on her theory about female development, writing that the maturity of girls depended on “shattering their self consciousness” by using their minds. In her letter, she wrote that Phyllis should think “how someone she dislikes would act in [a] situation—for she is free of self in thinking of someone she dislikes and how she would act. It is all a matter of using one’s brains and recollecting how little other people are ever thinking of those about them—any more than we are thinking of those about us”. She reassured her sister that it was natural for teenagers to be moody and melancholy, and she predicted that Phyllis would go through many other stages. All adults can do is to create wholesome conditions for them, her aunt wrote, and then “let them grow! Mother Nature is wiser than we are. Leave it to her. The flower too goes through many phases before arriving at bloom and fruitage.” She added: “If you could hear how every mother with her first daughter is astounded, dismayed, perplexed and discouraged you would take comfort.”

A year and a half later, Phyllis’s aunt decided that her niece was ready for a glamorous evening gown and a more sophisticated social life. “Aunt Mary has given me a new party dress!!!!!” Phyllis wrote to her mother. “It is a heavenly shade of blue with silver on it. It is rather of a turquoise blue and is chiffon with ends floating from it all around!!!” The aunt and niece then planned to go together to New York City to a Westover friend’s debutante dance at the Metropolitan Club. “Aunt Mary said she didn’t know whether I would have a good time, but it would add to my experience anyway,” the girl confessed to her mother.

Miss Hillard also freely gave advice to other parents about how to bring up their daughters. In a letter to the father of young Betty Choate, she first praised the girl’s personality, but then politely stated that she was immature and needed to spend a year in Europe. The headmistress also bluntly said that he and his wife should spend more time with their daughter. Many times, in fact, she advised parents to become less distant dominating figures and be better friends with their children. Speaking of all young people, she rhetorically posed a question to parents on Visitor’s Day in 1923: “How can you help them?” And then she gave the answer: “Give up authority—that was only to protect them. Substitute companionship,” she said, and “enter into their troubles and their ambitions.”


Girls encircling the West apple tree inside the Quad. WESTOVER SCHOOL ARCHIVE.

While the principal preached to parents, she also scolded pupils from time to time. She was strict about decorum, especially in the dining room, and girls rarely tried to defend themselves. When a spider dropped down the front of a new girl’s dress during dinner one time, she let out a cry. Everyone in the dining room became silent, and Miss Hillard told her to go to her sitting room after dinner, where the girl was informed about the time a mouse ran up another girl’s leg in chapel, but she remained silent and held onto it until the service was over. When the headmistress was dismayed by what she perceived as a diminishment in the spirit of the school, she would start what were called “reigns of terror” that lasted for days. In February of 1912, for instance, she went to the schoolroom “with trouble written all over her face” to talk about a prank the day before, when girls had dressed up a dummy in a uniform to fool a new teacher. Miss Hillard told the assembled school that the joke had, in the words of a student, “hurt her pride in the girls so [much] that she kept from breaking down before us only with the most heroic effort,” Jessica Baylis wrote to her parents. Then the headmistress asked those involved to stand up, and when they did, she spoke to them sternly.

A troubling aspect of Miss Hillard’s personality was her tendency to favor some girls over others. She evidently liked leaders and well-rounded students, partly because they were excellent examples to others. She begged the mother of Rachel Latta to send her daughter back to Westover after a year abroad, and when she did, Miss Hillard wrote that “I am glad for Rachel, and deeply glad for the school.” Rachel had impressed the principal during her sophomore year, and as a senior she fulfilled her promise and was named by the other pupils as the most studious and athletic student and the second best all-around girl in the school. She and another girl were also ranked the most attractive. Miss Hillard’s favoritism had its limits, however. Even though Rachel was a favorite, she lost her good conduct medal after sitting in front of the fireplace in the Common Room for an hour one night after lights out.

Although girls were not allowed to go away on weekends until senior year, when Theodate Pope Riddle invited her younger twin cousins for a weekend at Hill-Stead, Miss Hillard let them go, explaining that she was granting the favor to Mrs. Riddle, not to the girls. In another case, when Margaret Bush was a new girl and asked her headmistress if she could change roommates, she replied, “Margaret, I have never made a mistake in the kind of a girl I’ve admitted to Westover, but I see that I have made one in you.” Margaret felt crushed, but when the term was over Miss Hillard changed her mind and let her do it. (She declined.) The young woman turned out to be a leader who was elected president of the senior class, but in her opinion she and her sister were given special privileges only because their headmistress was so fond of their father. “Not everyone liked Miss Hillard because she had favorites,” admitted another student. “I liked her because I was one of her favorites.”

Although Mary Hillard knew that it was often difficult “for a girl to leave home and learn to stand on her feet,” as she put it to her sister Emily, she was not always sympathetic toward homesickness. “The shock and surprise and excitement of it often make a young girl really ill even though she may be really enjoying it,” she theorized. This attitude is evident in the case of Jeannette Rich, who spent most of her first months at Westover in the infirmary suffering from psychosomatic aliments caused by extreme homesickness. One day when she saw Miss Hillard in the hallway on her way to New York, she timidly asked if she could go home a few days early for Christmas vacation. The headmistress snapped at the girl that she could go home and stay home because she was physically, mentally, and morally weak. The girl burst into tears and rushed off to find Helen LaMonte, who comforted her throughout the rest of the day, until Miss Hillard telephoned and softened her harsh words. Later that year, when Jeannette was in the infirmary with a sports injury, the headmistress stopped in to see her, remarking that she was glad for the accident because it gave the girl a chance “to exercise fortitude.” Although shocked by her words at the time, Jeannette never forgot them and afterward even found them helpful.

While Miss Hillard’s discipline was often erratic, either too strict or too permissive, it was sometimes relieved by her sense of humor. In the late 1920s, she used to board the bus of girls going to Taft for a tea dance to make sure no one was wearing lipstick or rouge. Once when she ordered a pink-cheeked blonde to rub the rouge off her face, the petrified girl denied that she that she was wearing any. The headmistress, the girl remembered, “stared at me for a breathless second, and then with that twinkle that occasionally appeared, she said, ‘My dear, I congratulate you.’” Another time when a student took a dare to sleep in the headmistress’s bed when she was away and was discovered upon her early return, Miss Hillard was again amused.

Her way with girls, however, did not work as well with boys, at least with her nephew, Archibald MacLeish, a son of her sister Martha. When, at Mary’s urging, Archie was sent from his home near Chicago to Hotchkiss School, a boys’ preparatory school about forty miles from Middlebury, she became as close to him as she had been to her deceased younger brother John. “I have a new young nephew come East to school,” she wrote happily to a friend. “He spent Sunday with me and kept me inwardly smiling [because] he was so dear and unconscious and so funny.” That autumn her youngest nephews were christened in Westover’s chapel with Archie and a cousin acting as godfathers and Aunt Mary as godmother. The moving service, attended by relatives, friends, students, and staff (including the handyman, maids from the West Indies, and laundresses from Ireland), made her weep. A few weeks later she described the “chapel full of those lovely girls with their angelic reverent young voices chanting the hymns,” an experience that “makes one’s heart rise up to one’s throat.” After the christening, a few girls were invited to join the older boys in the headmistress’s sitting room, where she read Romanian and Irish folk stories aloud until the bedtime bell.

One spring evening when Archie was eating at the head table on a raised platform in the dining room, a senior asked the very pretty Ada Hitchcock to fill an empty seat. Eighteen-year-old Archie was immediately infatuated with Ada, but, after learning that he was writing her every day, his aunt tried to discourage the match. She thought he was too young to be in love, but there is another less benign interpretation. Ada was the daughter of a self-made merchant in Farmington, and Mary, according to family lore, wanted her nephew to marry a girl from a more prominent family, like Esther Cleveland, the daughter of a former President. The MacLeishes welcomed Ada warmly, however, and the pair planned to eventually marry after Archie’s graduation from Yale, where he was class poet. After his stint in the army and enrollment in Harvard Law School, a wedding date was set in June of 1916. Aunt Mary slowly came around, but in such a dominating way that Archie half resented her giving a dance for them, taking over the wedding rehearsal, and putting them up at Crossways the night before their honeymoon in Bermuda. (His sister, Ishbel, graduated from Westover that spring as president of her class and winner of the John H. Whittemore award for “Faithfulness, Justice, Truth, Humility,” then followed in her mother’s footsteps to Vassar.)

Miss Hillard thought her nephew would make a brilliant lawyer, perhaps fulfilling the promise of her beloved brother John, so she also opposed Archie’s growing interest in becoming a poet. When he turned down a partnership in a Boston law firm to move to Paris and write poetry, she furiously tried to talk him out of what she regarded as a bohemian way of life. During a bitter argument, she called him a Bolshevik and he responded by calling her a reactionary. Since she had always adored poetry and had introduced him to John Masefield, whom he regarded as the greatest living English poet, Aunt Mary was in a precarious position. “I do not think even she would argue that the law as a career is more desirable than letters,” Archie wrote to his mother. Again his parents backed him, and the young couple and their child moved to Paris.

It was one of the times when Mary Hillard was wrong about what was right for a young person. Many years later the Rev. John Dallas wrote about her tendency to be willful and wrongheaded. “There was a majesty and almost a fury in her love,” he observed. She “never knew or understood how she wounded,” but afterward would try “to put together again what she felt she had broken.” And, he went on, what often looked like possessiveness was her ability to see another’s potential. “It was not to superimpose her own will upon another that made her love seem a fury. Rather it was a desire deep within her intelligence and will … to compel the recognition of the vision which consumed her soul … Fire burns. The result often hurts.” Mary was well aware of this character flaw. “I too give pain without knowing I do when if I could exercise more imagination and restraint I would not do so for anything,” she admitted to her friend Harris Whittemore. In retrospect, it appears that much of the advice she gave her girls over the years was learned from her own excruciating experiences.

MacLeish’s anger deepened after his aunt wrote him in France that she disliked his poetry and so did the editors she showed it to. After she refused to read a published book of his poetry, Archie wrote his mother that “I have definitely, and, I am afraid, not very regretfully, broken with Aunt Mary.” He asked his aunt to stop writing and trying to see him. Nonetheless, his feelings remained ambivalent and while still abroad the couple named their newborn daughter Mary Hillard MacLeish. When they returned to the United States, Archie made a tenuous peace with his aunt, but his anger lingered. When she asked him to read his poetry at Westover the year before her unexpected death, he refused. After winning the Pulitzer Prize for poetry in 1933 a year later, he did give a reading at the school, and Ada gave a performance of French songs she had learned in Paris. He returned to Westover again a decade later when his daughter was unhappily enrolled, when he gave a dramatic and disturbing talk about his youthful falling out with the woman he later called his “intelligent and experienced and lovely” aunt. It gave him a feeling of release, but he still did not understand her devastating opposition to him as a young poet.

As a result of her love of poetry and the other arts, Mary Hillard also believed that a balanced life was a cultured life. Over the years, she invited a wide variety of excellent performers and lecturers to Middlebury to excite her students’ minds as well as to arouse their sensibilities and to train their tastes. Many of the visitors were men and women she had met or heard about during her travels and active social life. She was a member of many prestigious and exclusive clubs in America and abroad (including the Waterbury Club, the Chilton Club in Boston, the Colony Club and the Cosmopolitan Club in Manhattan, and the Ladies Imperial Club in London), where she enjoyed talking with interesting and informed people and associating with prominent ones. The year she turned fifty, for instance, she wrote her sister Emily from the Colony Club that she was glad to be meeting “so many people of distinction.”

Even earlier, while she was at St. Margaret’s School, she had drawn social worker Jane Addams of Hull House in Chicago and Professor Woodrow Wilson of Princeton as speakers. During Westover’s first full year, she took pupils to hear African-American educator Booker T. Washington in Waterbury and then invited him to speak in the school chapel. The next spring of 1911 her friend Theodate brought a house guest at Hill-Stead, writer Henry James, to Middlebury to see her handsome school. The girls, waiting for the well-known novelist in Red Hall, applauded when he arrived, but when he was taken to the schoolroom to speak to them, he smiled and bowed but said very little. “My mind has been undermined,” was about all he could say, according to Helen LaMonte. “On he went from there felicitating us upon the felicity of dwelling so felicitously in this felicitous setting. More applause. Much waving of hand and hat as he departed, his last sentence unfinished, so great a vocabulary that the choice of the right word was too difficult.” The next year a Yale professor lectured about the pleasures of reading, a talk that interested Jessica Baylis so much that she quoted him in her diary as saying that “the happiest people are those that [sic] have the most interesting thoughts.”

Although Miss Hillard was not musical herself, she loved music and encouraged a great deal of it at Westover. Singing began in morning chapel and ended with evening vespers. Everyone was given a voice placement test on arrival at school so she could sing her part in all the hymns, ballads, and school songs. Besides offering instruction in singing, piano, and violin, the school had a superb Glee Club under the direction of Isaac Clark, who was at Westover for years. “You are a delightful girl to remember your old man coach,” he wrote to a former student. “Such a glee club. I don’t believe there ever was such an one anywhere—my heart aches as I think of the future, the standard is so high—how can it be kept up—Certainly we do not want it to fall below this year … When one has looked forward to beautiful things all his life and has found them as I have with my work at Westover—and only there—perhaps you can realize what it all means to me … It is the one shining spot in my life—You are one of the few that know it.”

Besides singing, there was a great deal of listening. Music of the highest quality was performed in Red Hall every year, where a grand piano was stored in a large closet behind the wide landing on the staircase. The Budapest String Quartet started its season there for many years; the Stradivarius Quartet also performed as did members of the New York, Philadelphia, and other symphony orchestras. The list of individual musicians is long: in the fall of 1909, for example, a pianist gave a talk on Bach and then performed the master’s music, in 1917 the Tuskegee Singers sang Negro spirituals, and in 1924 the renowned Wanda Landowska played the harpsichord.

Miss Hillard, whose older sister, Helen, a nurse who had worked at the Henry Street Settlement House in New York, also wanted to expose her students to problems in society. In her belief that privilege brings responsibility, she had the reformer Jacob Riis lecture about the terrible living and working conditions of immigrants in American cities; in fact, the year that Westover was founded, thousands of members of the International Ladies’ Garment Workers had a strike in New York. Then in 1914 Max Eastman, the editor of the leftist magazine The Masses, arrived from Manhattan to lecture without wearing a tie; after one was put together for him from shoelaces, he spoke about slang, to everyone’s surprise. “There has been much speculation as to whether Miss Hillard knew what he was going to say,” wrote an editor of The Lantern afterward. “Anyway, she spent an hour in the schoolroom the next morning counteracting the effect.”

When school let out for the summer, the headmistress and her colleagues usually left for a few months in Europe. These trips were interrupted after the summer of 1914, when she and Lucy Pratt were in England as World War I broke out. A few years before in England, Mary Hillard had met poet John Masefield, who then visited Middlebury while in America on a lecture tour, and the two corresponded during the war. She asked him questions about the hostilities that he could only answer philosophically if at all, explaining that after being on the battleground for several months he had “no certainty of our purpose here.” In a letter written in April of 1917, he went on: “Now the biggest battle that ever was fought is raging, and I have been watching it from a hole in the ground in the biggest roar and racket that ever troubled the earth. It is not possible to describe it, except that there is over the earth, an angel of wrath, that is all angry and dark, a sort of threat or menace, not a night, nor a dust, nor even a smoke, but something made of all these, and reddish and rather threatening and all shot with blinks of very terrible fire, and it is like the very Devil of Hell sitting in the air enthroned … Up above, there are aeroplanes droning and casting glitters, and shells bursting (and larks singing) and a sky all blue with the spring.”

“I often think of Westover in these places of death and ruin and awful blasted horror,” he continued in his letter. “Westover is a very beautiful and a very happy memory to me, all kindness and happiness and bright dazzling winter weather, and a happy place to come to out of the cold and the night.” His vivid words from the trenches, which Miss Hillard read to her pupils, no doubt influenced her later devotion to the cause of world peace, as did the death in 1918 of Martha’s son, Kenneth MacLeish, a pilot with the Royal Air Force.

After America entered the war, pupils marched in military drills on the hockey field and participated in patriotic parades and events in Waterbury, including a pageant in St. John’s Church, when the girls waved the flags of the Allies and sang their national anthems. They also worked for the war effort by knitting clothes, making bandages, organizing a nursing course, and raising money for orphans. A red banner with the names of those in the school community who were most involved in the war effort was hung in the chapel. When the armistice was announced early in the morning of November 11, 1918, girls gathered in their nightclothes in Red Hall to listen to Miss Hillard, wearing a pink bathrobe and her hair still hanging in a braid down her back. She lead everyone in patriotic songs before they entered the chapel for an impromptu service. Later, students rang the bell in the tower until its rope fell off, and a large celebratory bonfire burned on the village green.

That year John Masefield returned to Middlebury to read his poetry and preside over what would become a yearly writing contest for seniors. The poet, who was later named poet laureate of England, gave the winner, Polly Willcox, a beautifully bound book as a prize for her short story about circus camels. Poets were always high on Miss Hillard’s wish list of visitors, and Walter de la Mare, another of the most famous poets of the day, also read his poetry there. A few years later William Butler Yeats arrived from Waterbury by sleigh after a snowstorm had made the roads impassable by automobile. Other lecturers during those years included a bishop from Kyoto who spoke about the position of women in Japan, a female scholar from Oxford University who talked about novelist Jane Austen, and a son of Leo Tolstoy who spoke about his famous novelist father.

Reformers and radicals continued to arrive in Middlebury to talk to the girls. Among them was gray-haired Catherine Breshkovsky, a member of the Russian intelligentsia, whose sympathy for the plight of the peasants in her country had led to her imprisonment and exile. Miss Hillard became aware of her plight and arranged for this woman, called Baboushka or “the little grandmother of the Russian Revolution,” to visit in March of 1919. When the visitor in a white headscarf and coarse brown robe glimpsed the West Indian maids, she rushed over to embrace them, calling them “dear children, not long from slavedom.” More fluent in German and French than in English, she dined with pupils at the French table, where she expressed displeasure at maids waiting on table and approval on hearing that girls made their own beds. One time while singing Russian folk songs to students, she spontaneously started doing folk steps under an apple tree in the Quad before suddenly turning serious again. “She seemed as she moved amongst us to create a wonderful atmosphere of heroism and eternal hope,” remembered French teacher Henriette Coffin.

Although Miss Coffin remembered that Baboushka had wondered whether the girls in “this house of so many riches” could comprehend the troubles in Russia, they raised money for her causes for years. In 1927 she sent an embroidered dresser cover to the girls of Westover along with a plea to help a young Russian woman scientist. “The letter was an appeal from a poor country to a rich one,” wrote an editor of The Lantern in the March issue. “But it was more than that,” she continued. “Written by a great woman, whose life had been spent, in every sense of that word, for her oppressed people, and who at her present age of eighty-three years has not the remotest intention of quitting her post, it contained an expression, in rather broken English, of the courage, enthusiasm, interest, hope, and appreciation of a very remarkable personality” whose “outlook on life is broad, varied, and alive, excluding only despair and defeat.” Baboushka’s countryman, Vladimir Zenzinoff, was touched by the way the old lady was remembered at Westover—“her name here is surrounded by a sort of halo”—and he noted in his memoir that photographs of her visit “are reverently kept by Miss Hillard as relics.” He observed that “time and again did she speak of the Grandmother and her life to her pupils, and these stories evidently formed a part of her educational system.”

Indeed, in Mary Hillard’s effort to teach the importance of philanthropy, she established the Dorcas Society, named for a Biblical woman known for her good works. Members of Dorcas sewed and knit clothes for the needy and undertook charitable work in the community. Every pupil was expected to give up dessert during Lent; as she left for church on Easter morning, she was given a gold coin she had earned for the donation plate. Girls also hosted a Christmas party for neighborhood children every year complete with a Santa Claus and gifts. After Miss Hillard took students to Waterbury to hear a talk by Sir Wilfred Grenfell, a quiet English doctor who ran a humanitarian mission in Labrador, they began to raise money for him as well. The headmistress also established a charitable Mary Hillard Society, which over the years gave away thousands of dollars to many causes, including churches, visiting nurses, girls’ clubs, crippled children, and missionaries in China.

Miss Hillard’s wide sympathies and worldly interests created a well-rounded life of her own, especially after the war when she was able to travel to Europe again. In 1928 she offered to take Ursula Van Wagenen Ferguson on her first trip to Europe. Ursula had been the admired president of St. Margaret School’s class of 1908, and after her graduation she was a chaperone at Westover for a while before her marriage. When she moved to Middlebury with her husband and young son and daughter, she renewed her friendships with the Misses Hillard, Pratt, and LaMonte. She became deeply involved in the life of the school and was eventually hired to oversee the Dorcas Society. During the summers when not in Europe, Miss Hillard liked to have the Sunday midday meal served outside in the Quad for whoever was around—her nieces and nephews, teachers and friends, as well as members of the Ferguson family—when “she would always try to stimulate the conversation to some interesting topic,” recalled the Fergusons’ son, John.

The women’s trip to Europe typified the busy, purposeful, and even grand way in which Mary Hillard traveled. Before their ship left New York, gifts of books and magazines, baskets of fruit, bouquets of flowers, and boxes of nuts and candies arrived in the stateroom. Perhaps it was on that trip when she gathered all the fresh flowers in her arms and dropped them into the sea right after the ship left port. “A withered flower is the size of a withered soul,” she liked to say. “She could not bear to think of so much beauty left to fade and decay—nor of such expressions of love and friendship allowed to wither and to be neglected,” explained a friend. Miss Hillard, Ursula wrote in wonderment to her husband, had seven pieces of luggage, including a hat box, a bundle of rugs, a box of books (including a three-volume history of England), and a tin box for picnic lunches. When the two arrived in Paris, they met up with Helen LaMonte (who was traveling with young Gertrude Whittemore and a school friend) as well as a number of acquaintances (including Vladimir Zenzinoff) for sightseeing and social, sporting, and cultural events. In England the two toured the countryside in a chauffeur-driven automobile, meeting up with Theodate, John Masefield, and a Westover alumna or two. Mary had many appointments in London, including a luncheon with Lady Astor at her home, and a meeting with two Englishwomen, a Miss Low and a Miss Michello, who would both teach at Westover the next year.

As a result of all that Mary Hillard brought to her community of females in Connecticut, attending Westover was much more than simply getting an education from books. The year the school opened, a girl perceived that she was learning the art of living, and others throughout the years would echo her words. Accordingly, it was at graduation near the end of her reign when the headmistress proclaimed that “your diplomas are precious to you because they are sign and emblem not alone of mastery of courses of study successfully completed. They are sign and emblem of more than that—the hidden and secret message running through them … [of] your loyalty to radiant, glorious, immortal, unchanging spiritual values with their ‘power to quicken, quell, irradiate, and through ruinous floods uplift’ the souls of men.” The years under her tutelage had taught Bidda Blakeley, for one, “about beauty and honor and all the wonderful qualities of life,” she remembered. “And thank heaven I went there.”

Westover

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