After the months in Europe, it was more evident than ever that the growth of Waterbury in the 1890s had become “phenomenal,” to use Mary Hillard’s word, as immigrants arrived to work in factories that were polluting its air with coal smoke. The city had, in fact, more than doubled in size since she had moved there. At a time when there was no cure for tuberculosis, Waterbury and other cities were dangerously overcrowded. Teachers and parents alike had begun to believe that the countryside was a more wholesome place for schoolchildren than a city. And, as a result, Mary believed that St. Margaret’s School was in peril.
Not only did Mary want to get away from the unhealthy conditions of Waterbury, she also wanted to offer girls the athletics and other advantages that were more available in the country. Most important of all, she fervently wanted to create a self-contained community devoted to teaching traditional moral values to daughters of the newly wealthy merchant class. By then in her forties, Mary Hillard was a self-possessed person with a regal bearing. Her dream was a real possibility because of her manner and persuasiveness with the St. Margaret’s board of trustees as well as her friendships with the Popes and other wealthy and influential Connecticut families. At a time in America when a newly emerging crusade for rights for women was gathering force, Theo’s resources and determination to build another building and Mary’s success as an educator and her missionary zeal were a potent combination.
Their plan emerged for a girl’s school for one hundred and forty boarders and their teachers. Mary and Theo had joined the Connecticut Society of Colonial Dames together in 1900, and the ultimate design was heavily influenced by the colonial revival style. It was not necessary to be licensed to work as an architect in Connecticut at the time, and Theo hired draftsmen and consultants as needed. On January 30, 1906, Mary proposed to the St. Margaret’s board that they build a new school building outside Waterbury for the boarding pupils; they eventually agreed to the idea, even permitting her to take along the boarders and teachers who wished to go with her. Then, after someone remembered that the school charter did not allow a move out of Waterbury, the board agreed to release Mary from her contract. When she handed in her resignation exactly a year later, she was asked to withhold it until the end of the school year, and she agreed.
Mary’s plan was already in place, however. In 1903 she had told the Miss Porter’s trustees of her plan to form a company and issue stock in it to raise the $200,000 to $300,000 that a new school would cost, explaining that a well-managed school was “an extremely good investment.” Four years later in 1907, she set up the Westover Corporation to sell three thousand shares of stock at a hundred dollars each, which would pay an annual dividend of six percent. She sold stock to everyone she knew—friends, relatives, parents of pupils—even St. Margaret’s trustees. The man who immediately bought the most stock was John Howard Whittemore of Naugatuck, a man of her father’s generation whom she had met through the Popes. After making his fortune in malleable iron castings, he had commissioned a number of McKim, Mead and White buildings in his native city. Mary knew how to appeal to Mr. Whittemore, since they were both descendants of old Connecticut families and children of Congregational ministers. She praised his philanthropy as “a true and honest source of right and high minded influence,” and, after receiving a grateful letter from her in 1907, he called his help “a labor of love.” After selecting the rose as the new school’s flower, she sent the Whittemores roses at Christmastime; she would also ask him to light the first fire in a school fireplace. After the pupils arrived in Middlebury, Mr. Whittemore used to ask her, “Are the girls happy?” He was the first president of the Westover Corporation and then the first president of the board of trustees until his death in 1910, a year after the school opened.
Theodate Pope around 1895. ARCHIVES, HILL-STEAD MUSEUM, FARMINGTON, CT.
It was because of the Whittemores that Mary’s school was built in Middlebury, where the family had a summer home, Tranquillity Farm. Before land was bought, the Popes’ chauffeur, Turner, used to drive Mary, Theo, and teachers at St. Margaret’s around the countryside in the family convertible motor car, nicknamed the “Yellow Peril” for its color, looking for sites for the school. (It was the first automobile that Mary had ridden in, and at first she had been fearful of its great speed.) They had driven through Middlebury in 1906 but considered it too isolated; the village had been bypassed by industrial development because it lacked waterpower, and most of its eight hundred residents still worked the land. But after Mr. Whittemore and his influential friends pulled strings, an electric trolley line was built from Waterbury to Woodbury with a stop in Middlebury, and it was possible to transport laborers and, eventually, students to the village.
With the help of John Whittemore and his son Harris, Mary pieced together a parcel of land along the south side of the Middlebury green that soon amounted to twenty-five acres. Involved in all the legal and financial details, she was so able that one of the shareholders, banker James S. Elton, said he regretted that because she was a woman she could not be president of the Waterbury National Bank. Mary wrote Harris Whittemore that she was “on fire” about her school, and when someone declined to buy stock, she would simply ask again. In 1907 Theo’s architectural plans were finished and Richard F. Jones of Hartford, a contractor who had built Hill-Stead and also worked for the Whittemores, was chosen. John Whittemore signed the construction contract in September, but before building could begin it was necessary to move the Methodist meetinghouse and its parsonage, the Middlebury general store and post office, a blacksmith shop, a clapboard farmhouse, and several towering elms. All but three apple trees in an old orchard were cut down, and the soggy pastures of a farm were filled to become playing fields.
Westover School under construction about 1908. WESTOVER SCHOOL ARCHIVE.
When word finally got out about the plans, there was an uproar. It was feared that the trustees as well as the principal were abandoning St. Margaret’s. At a meeting in November, alumnae and others presented two petitions protesting the loss of the boarders to trustee Chauncey B. Brewster, the bishop of Connecticut, but by then most trustees were already backers if not stockholders of “Mary’s school.” Finally Miss Hillard was forced to publicly explain. In a lengthy letter to The Waterbury American, she complained about being misquoted and misunderstood and heatedly defended herself and her plan for a new school. She wrote that she felt “naturally” entitled to take boarders and teachers with her to Middlebury because it was she who had attracted them to St. Margaret’s in the first place. She explained that prospective parents of out-of-town pupils worried about their daughters’ lack of athletics and “freedom of life” in Waterbury. The handwriting on the wall became clear, she went on, when her “own old girls” began urging her to do something so that they could send “their daughters to me” to be educated. She also pointed out that without boarders at St. Margaret’s, there would be more room for the Waterbury girls. Finally, she added that the pupils at the new school would continue to patronize Waterbury churches, concerts, hotels, and businesses. The storm blew over, but a newspaperman wrote sarcastically that the young ladies will go to Middlebury, “where the bloom of the cowslips is unpolluted and the rarified atmosphere untainted with the soot of industrial progress.”
This ivory tower had been estimated to cost a quarter of a million dollars, but by the time it was finished it would be more than twice that amount. Although Theo designed the building without a fee, she never felt constrained by a budget. As expenses mounted, more stock was issued; then in late 1908 when a large amount of money had to be borrowed,