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Creating a School:“A Real Girls’ Republic”

IN THE WESTERN WORLD THERE IS AN AGE-OLD DREAM OF womanly togetherness. Alongside the history of female exclusion from male institutions, there are stories of females voluntarily withdrawing together to embrace values that are absent in society. This tradition includes Amazon myths, Christian convents, and the Beguine communities of lay women during the Middle Ages. In 1405 Christine de Pisan wrote about an imagined City of Ladies devoted to the principles of Reason, Rectitude, and Justice. In nineteenth-century America, the antislavery, temperance, and other reform crusades gave birth to a feminist movement, and its aspirations were reflected in the nation’s poetry, plays, and political organizations. The early years of the twentieth century were the era of the educated “New Woman,” who was agitating for the right to vote, to contraception, and other forms of equality and emancipation. When the American Charlotte Perkins Gilman published a humorous fantasy about a peaceful female civilization in her periodical The Forerunner, many of its characteristics were already in place at Westover. Although no one knows whether Mary Hillard read those passages—which eventually turned into the utopian novel titled Herland—many of her ideals were taken from its pages.

In the fictionalized country that the author called Herland, women are not isolated, uneducated, ignored, inhibited, or dominated. When three young men discover this land, its women innocently challenge their assumptions about the nature of women. Gilman pictured a community of rose stone buildings set in a great garden and encircled by carefully tended forests of trees dedicated to the free and full development of everyone. This utopia pictures chaste courtship with men without the restrictions of marriage and the pleasures of motherhood through the parthenogenic births of daughters. Education, as well as enlightenment and empowerment, was a centerpiece of this ideal community. In her novel, Mrs. Gilman, the mother of a daughter herself, described spirited and fearless girls who were also eager learners. They were instructed in morality and other matters by the kind of reasonable, gentle, serene, and wise women that Miss Hillard wanted to bring to her school. The adults of Herland, in fact, looked like contemporary American women, the author observed, but without their “strained nervous look.”

In 1909, as the first full year of her school got underway, Mary Hillard herself, at the age of forty-seven, appeared dignified and self-confident. Likewise, Middlebury resembled the imagined Herland to a striking degree. The school’s first catalog, no doubt written by the principal, pictured it as “an old, quiet, orderly little village lying peacefully among the hills of western Connecticut … set in an intimate and beautiful park-like landscape broken by frequent streams and ponds, and dotted with the buildings, pastures, and woodlands of old farms, still largely owned and worked by the descendants of the early settlers. Removed from the activities and turmoil of our modern urban life, Middlebury furnishes an ideal environment characterized by the intimacy and the decorous simplicity of New England.” Originally inhabited by Algonquin Indians, the village was settled by English families in the early 1700s, and little had changed since then.

With its neocolonial façade of large shuttered windows, the school’s exterior echoed the village’s colonial past. Its square shape with everything—classrooms, bedrooms, offices, music practice rooms, a dining hall, schoolroom, gymnasium, library, infirmary, and chapel—under one roof was also reminiscent of the old scholarly and religious communities of Europe. Perfectly planned and proportioned as a place for girls and women, it was intended to create a sense of comfort and closeness. Certainly the sheltered cloister in the center of the school, where Mary Hillard hoped bulbs and bushes would blossom in early spring, suggested a sense of safety. One side of it called the Sally Port opened out to a view of the lovely Connecticut landscape. Many years later an architectural historian would note that the handsome and “prepossessing” quadrangle still fostered a feeling of community within.

Mary Hillard and pupils gathered in Red Hall, 1910. WESTOVER SCHOOL ARCHIVE.

In the early catalog, Miss Hillard went on to describe the inspiring aspects of the architecture. It blends “purpose with beauty, so that the sweet austerity, the charm and stately dignity of its academic and domestic atmosphere shall be an unconscious but constantly elevating influence endearing the place to all.” Older girls were supposed to initiate younger ones into this state of mind. And everyone else, pupils and teachers and administrators alike, was supposed to be affected as well. Like Sarah Porter, who had encouraged friendships between students and faculty, Mary Hillard wanted to break down barriers between the generations. “From today on you will realize more and more clearly there is no difference between us,” she would say to her girls. “We are all just pupils in the great school of life.”

Inside the large front door, the building was oriented both inward and outward—inward toward the grassy courtyard and out toward the rolling hills. The heart of the school was Red Hall, an airy two-story assembly room with a grand staircase encircled by a balcony, named for the blood-red color of its carpeting, curtains, upholstered couches, and extravagantly fringed and tufted velvet Victorian lampshades. Others believed the soul of the school was the small Gothic Revival chapel with its carved dark walnut woodwork and graceful arched window of clear glass. As so many backers of the school were Episcopalians on the board of St. Margaret’s School, the prayer books and hymnals were of that denomination, and the chapel was named after the same saint. It would be open to girls and speakers of all Christian faiths, so it was decided that the chapel would be dedicated instead of consecrated during a ceremony on a late October afternoon in 1909.

Expressing the understatement of the Arts and Crafts aesthetic of the time as well as the values of her childhood in a Protestant parsonage, Mary Hillard also explained in the catalog that “luxury” had been banished from the school for the “straightforward, perfect simplicity” of New England village life. For years afterward, she liked to tell the story about a girl who described Westover as just “a plain country school.” Instead of Victorian pretension, there was plainness for the most part. Walls were painted white and subdued colors, and the woodwork was stained dark, creating the impression of understated beauty. Bedrooms had mahogany bedsteads with white cotton bedspreads, and there were window seats and large closets with shelves for big hat boxes. The solid wooden furniture—including high-backed benches and long dining tables—was also designed by the architect. Many years later, Lucy Pratt wrote to her friend Theodate Pope that she was “living a lifetime in the midst of beauty you somehow, somehow knew the way to create.”

Outside, a formal garden was laid out, where brick walkways were edged with clipped boxwood in the English style. Beyond the Sally Port were a hockey field, tennis and basketball courts, and meadows and woodlands for picnicking and walking. Part of the farmhouse moved to make way for the school was named Crossways and used for cooking classes and parties. In 1916, two years after alumna Virginia Burns died in an automobile accident the summer after graduation, Virginia House was given by her grandfather in her memory; built on the far side of the hockey field, it was designed by Theodate for art and music studios. Around 1912 the architect had brought in noted landscape designer Beatrix Farrand, a niece of Edith Wharton who was in her twenties an original member of the American Society of Landscape Architects. Known for the restraint and refinement in her work, Farrand did a drawing for foundation plantings of woody and flowering shrubs, some of which were to be trained to grow against walls. The plant list has been lost, but her herringbone-patterned brick walkways and little garden house remain.

Miss Hillard emphasized the healthiness of the hilltop site in the catalog, explaining that “there is abundance of light, each room having sunshine for some portion of the day, and the air is kept pure by the most modern methods.” The Waterbury newspaperman who visited in 1908 noted that Middlebury was high enough for “pure air” but sheltered from winds by tall elms. He marveled at the school’s ultramodern steam plant, sewerage system, and entirely electric kitchen. Despite his fascination with the gadgets, he failed to mention the built-in vacuum cleaning system, but he did describe the clothes chute to the basement laundry and the little elevator for carrying cleaned and ironed clothes upstairs. Even though he raved about the supply of spring water and the raised water tank for automatic sprinklers and fire hydrants, he was unaware that there was not enough water. He also overlooked on exterior walls the stucco that had already begun to crack and crumble.

In the first full school year, 1909–10, about a hundred girls attended Westover including twenty-eight seniors. In the following years, the headmistress was so successful at recruitment that the size of the graduating class grew annually until it doubled to fifty-six in 1914. From the beginning, pupils came from as far away as California, Cuba, and Hawaii. When Katharine Talbott of Dayton, Ohio, visited the East, her friend Theodate Pope took her to meet Mary Hillard. Family lore has it that she was so impressed with Miss Hillard that she said if the school was in a tent or a tree house, she would send all her seven daughters to it. All but her eldest went to Westover, graduating in classes from 1909 to 1924. In gratitude, the family gave the school the Seven Sisters fieldstone fireplace in 1921, which was built in a meadow on the hillside behind the school.

Like Miss Porter, Mary Hillard sought “the right kind of girls,” daughters of industrialists, political leaders, and prominent families with inherited fortunes. A number of girls bore the surnames of well-known businessmen: Ford, Rockefeller, Singer, Underwood, DuPont, Goodyear, and Gillette. Some were even thought to be royalty. Jessica Baylis, a member of the class of 1912, wrote her parents that a younger girl, Agnes Irwin, was the daughter of a Japanese princess and an American father. When a Roman Catholic father wrote about enrolling his daughters, Miss Hillard discouraged him, saying the girls would have to go to Mass in an unventilated church in Waterbury overcrowded with what she called “the laboring class”; her underlying concern was undoubtedly the danger of diseases like tuberculosis. It is curious that she did not mention the little cobblestone St. John of the Cross Catholic Church in Middlebury next door, unless her letter was written before its construction was completed, or unless she thought it had one of the “poorly educated priests” of whom she expressed disapproval in the letter. She went on to call Westover “entirely undenominational, and we welcome girls of the Catholic faith, should they wish to come to us.”

“Westover is no place to enter your daughter unless you are thoroughly arrived,” reported Fortune magazine at the end of Mary Hillard’s reign. “When Miss Hillard takes Mid-Westerners, they are at least Mid-Westerners with an air: Lolita Armour; the Big Four—Ginevra King, Edith Cummings, Peg Carry, and Courtney Letts—who ruled the younger Chicagoans a few years back.” The four gave themselves this name because one social season they were the leading debutantes of Chicago. One wonders whether Miss Hillard had any regrets about what she regarded as the right kind of girl after a troubling incident with young Ginevra. She was the dark-eyed sixteen-year-old with whom nineteen-year-old F. Scott Fitzgerald fell in love when he was at Princeton. They wrote long letters to each other, and one weekend he traveled from New Jersey to Connecticut to see her. When he arrived at Westover, the teenagers chatted in what she had warned him was a “glass cage,” meaning a visiting room with glass panes in the doors. He never forgot the way the lovely brunette looked in her prim white evening uniform, and this image and others like it found their way into his fiction for years to come.

The night of the senior dance in the spring of 1916, a Yale boy threw a paste jar through Ginevra and her roommate’s open dorm window, and they and others leaned out to talk to the boys. When Miss Hillard heard about this, she flew into a rage and called Ginevra and two others to her office. “Well, she told us we were bad hussies’—‘adventuresses’—‘honey-combed with deceit’ etc etc—that ‘our honour was stained,’ ‘rep. ruined,’ ‘disgrace to school’ and the rest of her usual line and a lot more—But that was all very well—as we had done a foolish (not however disgraceful), thing and of course we had to take our punishment,” Ginevra wrote to Scott. The headmistress, however, went on and then asked them to leave school.

Ginevra telephoned her father, who was in New York on business, and he soon arrived. Miss Hillard had evidently reconsidered the expulsion and was “sweet as sugar to Father, even if he did tell her a few plain truths about herself—You wouldn’t have known her for the same woman,” the letter continued. Nevertheless, Mr. King insisted that Ginevra leave with him the next morning. After Miss Hillard sent him a letter “flattering me to the skies,” Ginevra wrote Scott, her father replied, accusing the head-mistress of “unjustness—unfairness and partiality,” and telling her that with her temper she should not be head of a school. Ginevra was so despondent about the incident with Miss Hillard, whom she called “a demon” in the letter, that she lost seven pounds. Her father refused to allow her to return to Westover for her fourth and final year, and she spent her senior year at a school called Miss McFee’s on West 72nd Street in New York City.

Ginevra later haughtily rejected her suitor, but Fitzgerald never forgot his first love. She was his model for the beautiful but unattainable girl he often wrote about, like Daisy Buchanan in The Great Gatsby. Ginevra as well as Westover appear lightly disguised in a number of other works. His short story “A Woman With a Past,” for example, describes an incident in which a headmistress of a girls’ school finds a laughing girl lying in the arms of an embarrassed young man after accidentally falling down steep chapel steps. “Unexpectedly, monstrously, just as it had begun to mean something, her school life was over,” the story goes, but not without adding that the prim and hysterical headmistress should really have been running a reform school.

Like Ginevra, most students came from homes with servants, but at Westover they were expected to make their beds and do other chores. Miss Hillard believed that wealth came with responsibility, and she was on a crusade to build character. In 1911 she noted with satisfaction that a girl from “an elaborate and luxurious home” was distributing clean laundry. A member of the class of 1914 remembered a classmate crying in frustration because her long hair had become tangled and matted, so her friend showed her how to brush it out herself and wind it back up on her head. Although tuition was one thousand dollars plus extra fees (Miss Hillard hoped, unrealistically as it turned out, to eventually reduce it after the school’s loans were repaid), the headmistress proposed that ten thousand dollars be set aside each year for scholarships. In her effort to instill down-to-earth values and interests in her pupils, she wanted to enroll daughters of professors, clergymen, and other middle class professionals. Her girls were told all the time that she expected them to use their privileges and expanding opportunities for the betterment of all. She was impressed by the way English boys’ schools produced pupils with high principles, who settled throughout the world like missionaries. “It is our aim to send graduates out to support civilization,” she would say to parents. “It is our hope to send them out into Vanity Fair fortified.”

No one knew which girls were on scholarship, and a rule banning jewelry and mandating uniforms tended to hide differences in wealth. In the fall of 1909 a tailor from the Abercrombie & Fitch department store in Manhattan arrived in Middlebury to measure for the uniforms that Miss Pope had designed. For classes there were khaki cotton dresses with detachable white starched linen collars and black silk Windsor ties along with brass buttons with the same Tudor rose as in the emblem over the front door; the day uniforms also had black patent leather belts with brass buckles stamped with the school seal and containing the motto. For afternoon walks there were tan corduroy skirts and camel hair polo coats with black beaver hats. Full bloomers made of nine yards of black pleated wool, worn with black stockings, white blouses, and gray sweaters were put on for sports. And for dinner in the evening the girls were to wear embroidered white voile dresses that went almost to the ground with soft wool capes in one of many different colors. “I think the freedom our handsome uniforms gave in their anonymity was symbolic. I can still feel the shock of Sunday, when for a few hours we reverted to our own clothes and a whole dreary world of complex gradations in taste, income, and social background suddenly sprang up only to vanish as we resumed our innocent and kindly round of uniformed school life,” recalled a pupil at the time.

Girls in evening uniforms and capes leaving chapel. WESTOVER SCHOOL ARCHIVE.

The importance of feminine values was emphasized in a 1909 issue of The Lantern, the school literary magazine, when it linked each letter in the name of the school with a virtue—womanliness, earnestness, sweetness, truthfulness, orderliness, vigor, enthusiasm, and righteousness. By adhering to these ideals, girls would learn “the very great art of living,” the editors earnestly explained in a high-minded way. Living in an idealistic community “creates mental responsiveness, stimulates liveliness of mind, and makes possible that interchange of humor, wit, and sentiment that makes the best fertilizer for the garden soil of civilized life,” Miss Hillard would write in an essay in her late sixties. She eventually established at Westover an honor system, which was explained in the initial issue of The Lantern every year. Perhaps it was instituted because of persistent misbehavior. Rebellions against rules and restrictions often took the form of eating forbidden foods in the big closets at night. When Elsie Talbott was class president in 1913, she failed to report that her roommate had hidden contraband chocolates in the covered chamber pot in their room. The honor system valued honesty, studiousness, neatness, loyalty, kindness, and consideration of others. Its existence meant that there were relatively few rules, even though every September Miss Hillard gave incoming students a long lecture about them. Decades later an alumna called it “a code of honor and an idealism which a little at a time I came to accept so joyously that I believed the most complete happiness I could possibly know would be if my life could in some way fulfill [it].”

School traditions were intended to endorse this idealism. The first year Miss Hillard introduced a number of ceremonies and songs including the school anthem, “Raise Now to Westover.” The autumn day when everyone was given a lantern to carry outside in the evenings soon became a lantern ceremony in the spring, a picnic with a big bonfire, games, and singing, when the headmistress lit a girl’s lantern from hers and whispered a few words of warning or encouragement about the strength of her metaphorical flame. The chapel was decorated with pine wreaths and boughs at Christmas and with white chrysanthemums and lilies at Easter. Repeating familiar rituals every year was a way to enforce loyalty to enlightened values, the headmistress believed. “Creation and presentation of beauty for its own sake is a constant enrichment of school life,” she would later write. Furthermore, she believed that such beauty would lead to “a life of harmony, proportion, sincerity, and happiness.”

In 1912 Mary Hillard had turned fifty, and as she lost her youthful slenderness, she gained a greater sense of presence. “Instead of any hurry in her walk there was balance and power, [and] at times she seemed to sweep along through the corridor or across Red Hall as if without effort,” recalled an observer. She spoke or read poetry in her lilting voice to girls in the chapel, the dining room, the schoolroom, and her sitting room. She greeted each girl as she arrived for breakfast in the morning, said good night after evening chapel, greeted them or said goodbye when they returned or departed for vacations; one year as she stood by the door in her cape before Christmas vacation, a girl nervously said “Merry Hillard, Miss Christmas,” and everyone burst into laughter. In her sitting room after dinner, Miss Hillard even talked one evening “in a wonderful way” about making less noise, Jessica Baylis wrote in her diary. Prettiness, the headmistress liked to say, has value only because of the pleasure it gives. And happiness has nothing to do with the pursuit of pleasure but with sacrifice of self and loyalty to high ideals. “Miss Hillard talked to us as she alone can, and as no one ever forgets,” wrote another girl in The Lantern in 1911.

That year the headmistress described in a letter to Theodate a morning, in which her pride in the school was palpable on the page. Before eight o’clock two girls were playing “the handle rolls of a Beethoven trio” in the gymnasium, as they did every day, she wrote. Others were polishing their shoes and tying black ribbons under their white collars in their tidied bedrooms, or reading in the library, or studying in the schoolroom, or crocheting in Red Hall. When the eight o’clock bell rang, “they all came streaming to prayers, to lift their clear young voices in the heavenly notes that fill our chapel and rise on high morning by morning,” she wrote. She felt warmth toward the young girls in her care and admired their “loveliness, spontaneity, and steadiness.” As she aged, “the solemnity [went] out of her face and in its place [was] a tenderness which often assumed a look of motherliness,” her young minister friend, John Dallas, observed. Eliza Talbott remembered that “she seemed to enfold us in a caring that was the real heart of our Westover experience.”

It was not always that way. Among “the triumvirate” that ran Westover—Mary Hillard, Lucy Pratt, and Helen LaMonte—it was Helen LaMonte who was called the balance wheel. A small, erect, slender person, she looked fragile but actually emanated force. When Miss Hillard flew off on tangents, it was she who gave her old friend a steadying hand. With her gentle and delicious sense of humor, Miss LaMonte would quietly calm everyone down with “bits of humor and wisdom scattered about,” a pupil remembered. One time the headmistress chose a few girls with flyaway curls for a club for those with fuzzy hair; she decided that its involuntary members would have to recite aloud Kipling’s poem “Fuzzy Wuzzy” as a form of penance. After Miss LaMonte heard about this, she told the girls to disband “because she had just returned from the Fiji Islands and feels quite at home among our ‘fuzzy heads,’” as one of the editors of The Lantern explained in the autumn of 1921. In her great enthusiasm and eagerness for adventure, the teacher had gone with a former student to the South Pacific, where they made sure to visit the grave of Robert Louis Stevenson. They had left New York on an old British India cargo freighter, “Lake of the Flowers,” with a few other passengers, including a screen writer and a man from Australia along with his performing dogs. There were “long days of good books and invented games and sleepy long, long thoughts,” remembered the former Betty Choate.

As assistant headmistress, Miss LaMonte did the administrative work she disliked in her small office to the right of the front door in Miss Hillard’s absence. Like other teachers at Westover, she, a Smith graduate, was among the first generation of graduates of most women’s colleges. Hired prior to 1900 at St. Margaret’s School, she was a widely read intellectual who loved to teach. In the classroom, Miss LaMonte’s method was one of “enticement” into the fascinating world of ideas. Her “attitude was that we were her equals come together for instruction and enjoyment, [and] it would be a breach of manners to behave ill in her class. Still, it did sometimes happen, if the playing fields were being mowed or the apple trees [were] in blossom, that someone was inattentive. This girl was asked quietly to depart and told she might wait in the corridor.” When necessary she pointed out errors with gentle humor and exquisite restraint. “What I remember most about Miss LaMonte was her way of expressing the necessary thing without being harsh or causing humiliation,” observed a graduate.

Dark-haired with a long nose and a penetrating look, she had very definite opinions. It was said that she had once marched down Fifth Avenue in a suffragette parade. She seemed to embody the highest ethics, indicating a slight air of scorn for what she regarded as inferior. Outspoken in a quiet way, she told girls, “when in doubt—don’t,” and urged them to be unafraid. With her twinkling eyes and wry smile, she drew to her those who were homesick, needed advice, or wanted permissions. She allowed a girl to use her office for a visit with a beau when the visiting rooms were taken, and at another time let her go to a Yale football game with him without a chaperone because his father was a well-known minister. “We opened our hearts to Miss LaMonte and adored to be near her. We could tell her our secrets and little problems, and she would always make us feel comfortable and happy. She radiated warmth and understanding and would always greet us with a smile and a word that made us feel adequate and at ease. She gave us a feeling of security and of being worthwhile,” recalled an early graduate. “And most of the time we were her heroines,” remembered Betty Choate Spykman. Miss LaMonte never thought girls did anything wrong, “and if we had a real success, whatever it might be, she rolled her eyes and clasped her hands in rapture.”

After her school had opened, Mary Hillard took more time for her private life. In fact, it was necessary for her to withdraw from time to time. It was on a Sunday in August of 1907 that she first met New York art connoisseur Augustus Jaccaci at Hill-Stead, when he was working on a book about private art collections. Mary described him in a letter to her sister, Emily, as “an Italian of aristocratic birth … very cosmopolitan, very brilliant, and with a rare simplicity and sweetness of nature which makes him one of the most delightful companions.” She soon asked him to make five hundred editions of Westover’s first catalog with gilt edges and a silk-lined slip jacket. She and the darkly handsome European she came to call “Jac” became dear friends. After he returned from a trip to Europe, she wrote him that “New York is a better place when you are in it,” and she sent him a share of stock in the Westover Corporation as thanks for his work. On her visits to New York during 1909 and 1910, they often dined and went to the theater together. “Our beloved (though sometimes misguided) principal returned from New York Saturday morning in excellent health and spirits,” observed Lucy Pratt. “She had been to concerts to her heart’s content by night and by day she had done more things than my pen knows how to write.”

Mary Hillard’s more than thirty surviving letters to Jaccaci have all the warmth, informality, and intimacy as those to her closest relatives and friends. “Dear Jac, you were such a deep comfort to me last night,” she wrote in one of them, saying how much she needed his friendship. Their closeness is indicated by her revelation of an important secret to him. “It was wonderful I could tell you what I did last night. You would know it is something I can hardly speak of—never do speak of—but I wanted to tell you Jac. For I want everything that makes you and me closer to each other. We each can help the other, we both need help. We are both generous, and generous people have especially human sympathy and affection, for they give out so much. Dear Jac, I’m so grateful to you, and I’m so grateful for what you were and meant to me last night.”

In the summer of 1910 she wrote to him in the most intimate manner, revealing that she enjoyed his manliness and felt he appreciated her womanliness. Writing from a vacation cottage in the woods, she alluded to the demands of what she called her “big ‘job,’” and asked him to imagine “what, under those circumstances, the brilliancy and cultivation of your mental powers is to me—the joy of having that in a companionship!” After he referred to her as “Mother Mary,” she rhapsodized that “you read my heart.” She went on: “You need me and I am here, and motherliness is measureless. You may be what you will—glad, grave, weary, troubled—It is all the same. It makes no dif-ference to the great deep understanding that knows you and cares. No one else could understand. But we do. We are both so simple. We both need companionship, comfort, healing, in this pathway of life which is so hard for each … you need the tenderness and the cherishing that wells in a woman’s heart. And I need the strength and courage that lives in high manhood.”

A few months later, in early January of 1911, when the man she had called her truest of friends suggested bringing visitors to Westover on a Sunday, she charmingly turned him away. “What a nice party you suggest! And how inhospitable not to say ‘Do come.’ But—dear Jac—the work we have to do here is something tremendous. It calls for all one’s wisdom to know how strength and vitality and powers of the mind can be so safeguarded as to be equal to the demands of schoolwork—and be fresh for it, and full of the joy of working. (My new secretary says, ‘I am so enjoying working here. This is such a happy place. Everyone is so happy. I love the work here.’) I have seen clearly that our hope lies in our quiet winters. Spring and Fall our friends come in great companies. We love to have them; we welcome them. Our safety lies in absolutely quiet Sundays, and in this blessedly quiet winter term. I have no right ever to go against my judgement in these things. You understand fully. So tempting as your attractive party is I know I am doing my bounden duty to Westover in asking you to wait over the Spring term. I shall love to have you all come up some day in May [if] you care to.”

She continued: “And as guests must be at times excluded from the home, so that these beautiful, living vital influences of the home may have freedom to gather and express themselves, just as flame springs from the log, and transforms the grey cold fireplace into a source of light and warmth, so the same conditions must be maintained in the life of such a kind of school as this is, that here may be that mysterious warmth and light and intimacy that comes in separation from the outer world, when the vitality within us, not taxed with social demands, may turn to the intimate daily life and the joy of that fellowship. That is what this beautiful snowbound winter term is to us. We protect it. Should we not? Even if it sometimes, as now, [it] becomes suddenly difficult to do so because one would rather not?”

After so firmly putting the mood of her beloved school above their relationship, either her letters to him ended or he no longer saved them. She continued to turn to him at times, to make memorial books for John Whittemore and Alfred Pope, for instance. After war broke out in Europe, Jaccaci returned to Paris, where he helped French and Flemish refugees. In the winter of 1915 he wrote to her with thanks for getting “the whole of Westover” involved in his cause, for which the King of Belgium later honored him. After the armistice he returned to Middlebury one more time, in 1919, when he signed the handsome leather-and-gilt school guest register he had designed many years before.

Mary had confided to “dear Jac” about her difficulties with Theodate, a member of the school’s board of trustees, who, she wrote, seemed “troubled and tremulous at the slightest suggestion of anything connected with Westover.” After the school had opened, tensions had arisen between the two strong-willed women. “Genius, and she has it, needs the kind of love somewhere that childhood needs. I give it to Theo very imperfectly because I think of myself too much (partly because the demands of daily life attack one so fiercely),” Mary wrote to him after Theo had sailed to Europe without saying goodbye. Photographs of Westover were included in an exhibit of the Architectural League of New York in 1910, and Cass Gilbert, president of the American Institute of Architects, later praised the structure as more “beautifully” designed than any girls’ school in the country. The two came up with the idea of giving her a gold medal inscribed “Theodate Pope, architect, 1910” in a leather case to help “dissolve that intangible something—we do not know what—that has seemed to send a frost through her thoughts of me.” (Theodate would finally be elected to the American Institute of Architects in 1918 and licensed to practice architecture in Connecticut in 1933.)

Problems had arisen between the two friends, because Theodate Pope would unexpectedly descend on Middlebury with a group of people to show them “her” school and receive a cool reception from Mary, who was fiercely protective of the school routine. “I think this attitude of not welcoming guests at all and every time hurts my dear Theo. I am placed in a dreadfully hard situation. But Westover does not exist as a monument to her genius, any more than it exists as an excuse for social pleasure for me. It belongs to its pupils. It was built for that. It is theirs,” she wrote to Jaccaci. It is for this reason that Mary established a surprise holiday when Theo was gladly welcomed back. In 1911, the year when Alfred Pope became president of the board, Theodate’s Holiday was announced by his daughter herself at breakfast on the last day of May. Despite tensions between the two women, Mary defended her former pupil and old friend whenever she ruffled feathers, as she frequently did. In a letter to Theo’s old beau, Harris Whittemore, she described a moment when “Theo took my hand most intimately, looked straight into my eyes and said, ‘You are my old Mary, are not you. Yes, you are my old real friend’ with entire trust. You will understand, with me, why we must all stand by her.”

In the spring of 1915, Theodate impulsively sailed to England on the luxurious Lusitania for a meeting of the Psychical Research Society in London, despite warnings about German submarines. After it was reported that the passenger ship had been torpedoed and quickly gone down, Mary rushed to Mrs. Pope’s side in New York as they anxiously awaited word of Theo’s fate. As Theo clung to an oar and thought she was going to drown, she counted the buildings she had designed, she later wrote to her mother. After hours in the ocean, she was pulled out and left for dead before someone noticed her eyelids flickering. Almost a year to the day after her rescue, Theodate’s Holiday had to be renamed Mrs. Riddle’s Holiday, after suddenly, at the age of forty-nine, she married John W. Riddle, a tall, thin American diplomat with a large handlebar mustache. Mary slyly suggested in a letter to a sister that it was fortunate that Mr. Riddle had a lot of diplomatic experience. Still, Theo’s former teacher was one of the few guests invited to the small wedding in Farmington, where the bride wore pale blue and carried a silver-tipped walking stick. She soon fulfilled her girlhood dream about raising orphaned children in the country.

While Theo was trying to adjust to married life, Mary was attempting to perfect her community of girls and women. She was well aware that in any group a hierarchy develops, particularly among young girls. Some liked each other too little, the headmistress thought, and others liked each other too much. Pupils were often warned about the problems. In the May 1920 issue of The Lantern, an editor cautioned classmates about finding fault with each other. “We are terribly critical here, of each other, and we have no right to be. If anyone outside of the school asked you what the girls of Westover were like, you’d have the nicest things possible to say, and they’d be perfectly true. Why, then, when we’re here together do we let criticism play so large a part in conversation?” The following year the December issue addressed the problem of exclusionary cliques. “It is always natural that one should see more of certain people than of others … But does no one feel that at times we let ourselves become so intimate with a certain group of girls, that we lose entire sight of many others? … The result proves to be that we are often, perhaps unconsciously, hard, hasty, and unkind.”

Miss Hillard discouraged cliquishness by encouraging girls to follow their interests in school publications and in dramatic, language, and other clubs. “She wanted everyone to be friends with everyone else,” a pupil recalled. When a group of ten or so girls formed a secret society in the 1920s, they knew that if the headmistress found out, she would be furious and forbid it. It was also assumed that she would look unkindly on requests to change roommates. The influence of cliques varied from class to class, of course, but it was an excellent sign that pupils were mindful of the attitude against them and addressed the issue openly. So is the fact that some graduates remember no unfriendliness at all. “I can remember little meanness and no cruelty,” recalled a student long after graduation, only “a simple, generous, and harmonious atmosphere.” Certainly Mary Hillard had a high regard for friendship. As she had written to Augustus Jaccaci, friendship is “much deeper than [the] exchange of thought, that is part of it, and a beautiful and stimulating part, but exchange of sympathies, and of courage, and of comfort may all be silent yet how tremendous is the difference it makes to have them. Such exchange is nothing short of spiritual.”

While she encouraged female friendships, she was wary of what she called “exaggerated friendship.” This was one of the topics that she talked to her girls about. In the December 1911 issue of The Lantern, an editor mentioned that “Miss Hillard’s annual talk on crushes came the other day,” but she did not elaborate on what the headmistress had said. When “crush” became a forbidden word, girls used other words like “want” and “tra-la” for it. Nevertheless, the adolescents exchanged valentines and flowers, made dates for going to chapel and concerts together, and slept in each other’s rooms and even in their beds. Younger girls who idolized older ones would go into a senior’s bedroom in the morning to shut her window or make her bed. This was natural and appears to have been much more emotional than erotic. Jessica Baylis confided to her diary that she had a crush on a senior named Polly, and she carefully kept count of the number of times—eight—that she had slept in her room. In her case, it was innocent enough: “I can safely say that I never learned to love any girl so much in so short a time. The most I did was to tell her that she was a dear and give her a bear hug.”

Such infatuations are commonplace in an isolated and sequestered female community. Besides being way out in the country, Westover was surrounded by a seven-foot fieldstone wall. Within the school, it was forbidden to read newspapers that reported scandals. In this atmosphere, Miss Hillard gave sensible advice about health: she warned girls about smoking, too much dieting, and about drinking more than one cocktail at a time. Other more benign behavior was under scrutiny. Besides being marked on room tidiness, girls were graded for their posture. If someone yearned to be alone for a while, she could place a sacrosanct sign that read “Please Excuse” on her bedroom door or on a pile of books asking respect for her privacy or possessions. The cure for low spirits was considered to be going on a long walk or doing something for someone else.

An outsider’s eye offers another perspective, so it is fascinating to read the description of a visit to Westover in February of 1925 by a Russian political exile named Vladimir Zenzinoff. Mary Hillard had an intense interest in the Russian Revolution, and she invited him to Middlebury to give a talk. Undoubtedly eager for the generous lecture fee, he agreed and was met at the Waterbury train station by a teacher and driver in a luxurious automobile with a fur throw. They drove over the snowy, wooded, hilly landscape to the three-and-a-half-story school, which Zenzinoff described as “an enormous and elegant stone house.” Middlebury in winter vividly reminded him of his village in Russia, and his descriptions are reminiscent of Charlotte Perkins Gilman’s imaginary Herland, too. “It seemed to me as if I were in a fairy tale,” he remembered, and his three days at Westover would turn out to be “unquestionably … the most pleasant, cheerful days [and] the most interesting” of his four months in America. His guest room “had a distinctly maidenish atmosphere about it … purity, immaculateness, a naive simplicity [with a] … snow-white, comfortable bed near the window.” But in some ways—the electricity everywhere and telephone in his room—the school did not remind him of his native land at all.

After being told that dinner would be in half an hour, the visitor, who spoke French but little English, admitted to himself that “still I did not know what sort of a school it was, where I was, nor who would compose my audience.” A group of teachers met him in the small dining room along with Mary Hillard, “who in her majestic bearing reminded one of Catharine the Great.” Through the door to the adjoining main dining hall, he heard the sound of “gay” young voices and tried to look inside, but all he could see were “rapidly moving white silhouettes.” Then he understood. “It appeared that I was in a school for—girls! Fear seized me, but soon this gave way to the courage of despair!” After dinner Miss Hillard led him to her sitting room, which was softly lit and warmed by a fire. He noticed a Russian samovar, which had been electrified to boil water more quickly. There were bookcases and upholstered furniture, as well as a piano and a large round table covered with books and magazines. “Seldom had I seen surroundings more comfortable, more attractive, more cultivated,” he wrote in his memoir.

Soon his hostess was called away, and Zenzinoff realized that what he called an “enormous, magnificent” room—Red Hall—was filling up. “Girls’ voices coupled with laughter became more and more audible, then suddenly silence reigned and I heard Miss Hillard’s voice.” She entered the sitting room where he waited and asked him to follow her, which he did with trepidation. In the big room “broad rows of chairs [were] densely covered with white figures,” he remembered. “On this white background only the faces [stood] out, blonde and chestnut heads, and an ocean of young, eager, radiant eyes. The entire audience was composed of girls of the most charming age—fifteen to eighteen.” Then the headmistress turned to the visitor and asked him a question: “We women listen and understand better when we have our hands busy—will that bother you, Mr. Zenzinoff?” He replied that it would not, and to his astonishment the girls pulled out their needlework. When he began to talk in halting English about the hardships of the Russian people under the Bolsheviks, he saw “sad amazement” on their faces. “To them, who had been accustomed to democracy, to an atmosphere of independence from childhood, all this seemed to be the height of insanity and violence. And wherever it was necessary, the dear girls laughed or were indignant. Wherever it was possible, they applauded. And at the end they recompensed me with prolonged applause, which seemed to me quite an ovation.”

During the next few days, the Russian observed daily life at the school for girls. Each morning as a breakfast tray was brought to his room, “somewhere near—as if having just waited for this moment—a delicate feminine voice would start to sing and someone’s hesitating fingers would play on the piano. Evidently the mysterious singer was practicing some hymns.” After lunch he was taken to watch pupils play ice hockey on the frozen pond. All day, he noticed, there was “animated conversation, laughter, gayety [sic]. Childishness, combined with maidenish gracefulness, but without even a shade of coquetry.” He had exactly the same experience as the fictional young men who stumbled on Herland: “Meeting me, the girls smiled in a friendly way, but without a trace of accentuated curiosity, not to speak of bashfulness—my greetings were answered with friendly words, and open, clear eyes.” He attended a play one evening and, after reluctantly saying good night, he immediately regretted refusing to go tobogganing in the moonlight with a group of teachers.

A view of the front of the school and the headmistress’s apartment from the chapel. SVEN MARTSON.

After his visit, the Russian revolutionary’s hope for a joyous new kind of existence began to seem real. “I think that those who have spent the years of their girlhood in the school of Miss Hillard must keep for life the wonderful sensation of the possibility of such marvelous fullness of life,” he wrote. “Does not here lie the inmost, the most important aim of education—to awaken in the young conscience for the rest of her life a longing for what in youth had already seemed half attained, as if in a dream?” He added that, contrary to the morning prayer of the Jews about not being born a woman, “I would have been glad to have changed for a month into a girl of eighteen and to spend that month in the school of Miss Hillard.” It is, he concluded, “a real girls’ republic.”