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.