MARY HILLARD HAD ALWAYS WANTED HER SCHOOL TO BE A place devoted to the wholesome values of her girlhood, the same ones that had shaped the grandmothers of most of her pupils. Life at Westover would be “simple, sincere, and natural,” she had written in the school’s first catalog. Her own childhood had consisted of “an education which brought her soul in touch with God, her mind in contact with the great thinkers of the past and present, [and] her body in contact with nature in all her aspects among the hills of Connecticut,” in the words of a her minister friend in Waterbury, John Dallas. As she structured a way of life for her young charges—one she envisioned as a balanced existence—she hoped that they would adopt it as their own after graduation. Some activities and traditions were similar to those in other girls’ schools, and others were unique to Westover. Mornings were for classes, afternoons were for exercise, and evenings were for studying in the schoolroom, or dancing in the gym, or attending events in Red Hall, or listening to the headmistress read aloud in her sitting room.

      The first Westover yearbook, for the 1911–1912 school year, indicates the way the days made up a routine, marked by traditions, in a rhythm that would be repeated for years. On many Saturday nights there were “germans” (a word meaning little plays), parties with songs, favors, costumes, and skits put on by the seniors, athletic teams, and others. From the first year there was the performance of a nativity play in the style of an old English pageant before Christmas vacation. Early on Easter mornings the seniors surprised the new girls by awakening them while walking down their bedroom corridors singing hymns. For a few years there was also a May Day dance with a queen and maidens, along with singing, dancing, and the winding of a Maypole.

      As always, there was the emphasis on building strength of character. Echoing Mary Wollstonecraft, an early Westover catalog stated that the goal of academic work was to train the mind to reason and to control the emotions. The importance of thought was underscored by the motto on everyone’s brass belt buckle, “To Think, To Do, To Be.” Learning, Miss Hillard believed, should also stimulate originality and inventiveness: “A person of liberal education should radiate life and joy and color by passing everything through the prism of the imagination,” she liked to say. Freshman year studies were intended to develop concentration, while subsequent years were planned to inform and train pupils’ tastes in art and literature. All this education reached an epitome in the senior year. “The studies of the Senior Year, which the thirty odd other lovely girls who will make up our Senior Class next year are to have, are of an especially cultivating character,” Miss Hillard wrote persuasively to the mother of a prospective student who had spent the previous year in Europe.

      Besides offering classes in art and literature, the school had many others in European and American history as well as a few in psychology, mathematics, astronomy, geology, physiology, and botany. The learning of languages, including Latin and Greek, was stressed, and plays were performed in German and French. Although the headmistress did not emphasize academics to the exclusion of everything else, she did, unlike Sarah Porter, put pressure on pupils by ranking them academically and reading aloud the list from highest to lowest on a day that was dubbed “Black Monday,” a practice modeled on boys’ schools. She also scolded poor performers. When freshman Marianna Talbott got the lowest grades in the school, Miss Hillard “gave me plain hell in front of the whole school,” the girl wrote in her diary. To encourage good grades, the principal established a policy that allowed a new girl who got over ninety in every lesson in a week to read in the library instead of going to study hall in the evenings.