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.
