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
