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