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