Even earlier, while she was at St. Margaret’s School, she had drawn social worker Jane Addams of Hull House in Chicago and Professor Woodrow Wilson of Princeton as speakers. During Westover’s first full year, she took pupils to hear African-American educator Booker T. Washington in Waterbury and then invited him to speak in the school chapel. The next spring of 1911 her friend Theodate brought a house guest at Hill-Stead, writer Henry James, to Middlebury to see her handsome school. The girls, waiting for the well-known novelist in Red Hall, applauded when he arrived, but when he was taken to the schoolroom to speak to them, he smiled and bowed but said very little. “My mind has been undermined,” was about all he could say, according to Helen LaMonte. “On he went from there felicitating us upon the felicity of dwelling so felicitously in this felicitous setting. More applause. Much waving of hand and hat as he departed, his last sentence unfinished, so great a vocabulary that the choice of the right word was too difficult.” The next year a Yale professor lectured about the pleasures of reading, a talk that interested Jessica Baylis so much that she quoted him in her diary as saying that “the happiest people are those that [sic] have the most interesting thoughts.”
Although Miss Hillard was not musical herself, she loved music and encouraged a great deal of it at Westover. Singing began in morning chapel and ended with evening vespers. Everyone was given a voice placement test on arrival at school so she could sing her part in all the hymns, ballads, and school songs. Besides offering instruction in singing, piano, and violin, the school had a superb Glee Club under the direction of Isaac Clark, who was at Westover for years. “You are a delightful girl to remember your old man coach,” he wrote to a former student. “Such a glee club. I don’t believe there ever was such an one anywhere—my heart aches as I think of the future, the standard is so high—how can it be kept up—Certainly we do not want it to fall below this year … When one has looked forward to beautiful things all his life and has found them as I have with my work at Westover—and only there—perhaps you can realize what it all means to me … It is the one shining spot in my life—You are one of the few that know it.”
Besides singing, there was a great deal of listening. Music of the highest quality was performed in Red Hall every year, where a grand piano was stored in a large closet behind the wide landing on the staircase. The Budapest String Quartet started its season there for many years; the Stradivarius Quartet also performed as did members of the New York, Philadelphia, and other symphony orchestras. The list of individual musicians is long: in the fall of 1909, for example, a pianist gave a talk on Bach and then performed the master’s music, in 1917 the Tuskegee Singers sang Negro spirituals, and in 1924 the renowned Wanda Landowska played the harpsichord.
Miss Hillard, whose older sister, Helen, a nurse who had worked at the Henry Street Settlement House in New York, also wanted to expose her students to problems in society. In her belief that privilege brings responsibility, she had the reformer Jacob Riis lecture about the terrible living and working conditions of immigrants in American cities; in fact, the year that Westover was founded, thousands of members of the International Ladies’ Garment Workers had a strike in New York. Then in 1914 Max Eastman, the editor of the leftist magazine The Masses, arrived from Manhattan to lecture without wearing a tie; after one was put together for him from shoelaces, he spoke about slang, to everyone’s surprise. “There has been much speculation as to whether Miss Hillard knew what he was going to say,” wrote an editor of The Lantern afterward. “Anyway, she spent an hour in the schoolroom the next morning counteracting the effect.”
When school let out for the summer, the headmistress and her colleagues usually left for a few months in Europe. These trips were interrupted after the summer of 1914, when she and Lucy Pratt were in England as World War I broke out. A few years before in England, Mary Hillard had met poet John Masefield, who then visited Middlebury while in America on a lecture tour, and the two corresponded during the war. She asked him questions about the hostilities that he could only answer philosophically if at all, explaining that after being on the battleground for several months he had “no certainty of our purpose here.” In a letter written in April of 1917, he went on: “Now the biggest battle that ever was fought is raging, and I have been watching it from a hole in the ground in the biggest roar and racket that ever troubled the earth. It is not possible to describe it, except that there is over the earth, an angel of wrath, that is all angry and dark, a sort of threat or menace, not a night, nor a dust, nor even a smoke, but something made of all these, and reddish and rather threatening and all shot with blinks of very terrible fire, and it is like the very Devil of Hell sitting in the air enthroned … Up above, there are aeroplanes droning and casting glitters, and shells bursting (and larks singing) and a sky all blue with the spring.”
“I often think of Westover in these places of death and ruin and awful blasted horror,” he continued in his letter. “Westover is a very beautiful and a very happy memory to me, all kindness and happiness and bright dazzling winter weather, and a happy place to come to out of the cold and the night.” His vivid words from the trenches, which Miss Hillard read to her pupils, no doubt influenced her later devotion to the cause of world peace, as did the death in 1918 of Martha’s son, Kenneth MacLeish, a pilot with the Royal Air Force.
After America entered the war, pupils marched in military drills on the hockey field and participated in patriotic parades and events in Waterbury, including a pageant in St. John’s Church, when the girls waved the flags of the Allies and sang their national anthems. They also worked for the war effort by knitting clothes, making bandages, organizing a nursing course, and raising money for orphans. A red banner with the names of those in the school community who were most involved in the war effort was hung in the chapel. When the armistice was announced early in the morning of November 11, 1918, girls gathered in their nightclothes in Red Hall to listen to Miss Hillard, wearing a pink bathrobe and her hair still hanging in a braid down her back. She lead everyone in patriotic songs before they entered the chapel for an impromptu service. Later, students rang the bell in the tower until its rope fell off, and a large celebratory bonfire burned on the village green.
That year John Masefield returned to Middlebury to read his poetry and preside over what would become a yearly writing contest for seniors. The poet, who was later named poet laureate of England, gave the winner, Polly Willcox, a beautifully bound book as a prize for her short story about circus camels. Poets were always high on Miss Hillard’s wish list of visitors, and Walter de la Mare, another of the most famous poets of the day, also read his poetry there. A few years later William Butler Yeats arrived from Waterbury by sleigh after a snowstorm had made the roads impassable by automobile. Other lecturers during those years included a bishop from Kyoto who spoke about the position of women in Japan, a female scholar from Oxford University who talked about novelist Jane Austen, and a son of Leo Tolstoy who spoke about his famous novelist father.
Reformers and radicals continued to arrive in Middlebury to talk to the girls. Among them was gray-haired Catherine Breshkovsky, a member of the Russian intelligentsia, whose sympathy for the plight of the peasants in her country had led to her imprisonment and exile. Miss Hillard became aware of her plight and arranged for this woman, called Baboushka or “the little grandmother of the Russian Revolution,” to visit in March of 1919. When the visitor in a white headscarf and coarse brown robe glimpsed the West Indian maids, she rushed over to embrace them, calling them “dear children, not long from slavedom.” More fluent in German and French than in English, she dined with pupils at the French table, where she expressed displeasure at maids waiting on table and approval on hearing that girls made their own beds. One time while singing Russian folk songs to students, she spontaneously started doing folk steps under an apple tree in the Quad before suddenly turning serious again. “She seemed as she moved amongst us to create a wonderful atmosphere