The creation of Hill-Stead gave Theodate a valuable apprenticeship during which she learned how to convey her ideas to draftsmen and to coordinate the work of landscape architect, contractors, and subcontractors. Nevertheless, there was to be no immediate sequel to such an auspicious beginning. The stress of making so many decisions had taken its toll, and Theodate collapsed after the house was nearly completed in the summer of 1900. She was exhausted not only physically and mentally, but above all, spiritually. A rest cure, followed by camp at Squam Lake with Mary Hillard and their friends, gave some respite but did not restore her sense of purpose or former sense of well-being. A diary entry in the fall of 1900 conveys her mood:

For years I have been keen on architecture and felt that the ugliness of our buildings actually menaced my happiness and felt breathlessly that I must help in the cause of good architecture. But I have wrung my soul dry in that direction over father's house.... And now I find that my material world is losing its power to please or harm me - it is not vital to me anymore. I am turning in on myself and am finding my pleasure in the inner world which was my constant retreat when I was a child.... I used to feel a frantic anxiety to uphold the best expressions in material art and felt that that was in itself enough to occupy one's life with. I might have known where I was landing - pictures have been dead long ago to me - the ones that please me, please only at first sight - after that they are paint and nothing more; to use a vulgar expression "sucked lemons." My interest in architecture has always been more intense than my interest in any other art manifestation. And on my word I think its not dead yet - not quite. If I only knew how to help the cause of good architecture! But I am tired of seeing these fluted flimsy highly colored hen houses going up - and am tired gnashing my teeth over them.¹

Instead of pursuing an architectural career, Theodate concentrated on charitable deeds. In the summer after the Popes had moved into Hill-Stead, she noted in her diary:

I can now say we are leading the life I have meant we should if it was ever possible. A large simple home to receive our guests in - and the right kind of guests and leisure to live in.... I want my head in the spiritual world and my hands in this one to help others.²

Hoping to teach a skill and a discipline to children in Farmington, Theodate had started a sewing school in 1897.³ Perhaps she remembered the cooking and sewing school she had seen at the People's Palace in London, and Walter Besant's heroine Angela who had taken on the role of seamstress in order to aid the feminine poor in East London. Sewing classes and other crafts were being taught at settlement houses that, inspired by London's Toynbee Hall, were being created in some of America's largest cities. Theodate hired teachers from Hartford. She provided hot chocolate with whipped cream and cookies, and perfect attendance was awarded one dollar, or fifty cents if less than perfect, at a tea party and exhibition culminating each term. When she decided to expand her endeavor to include a cooking school, the Ecclesiastical Society, which was building a new parish house, gave her its chapel on the village green. Relocated and renovated, it opened in the fall of 1901.⁴ The following year she recruited Amy Hicks from the New York Guild of Arts and Crafts to teach rug making, hoping that this might become a source of income to some of the village girls. She had also become interested in the local boys club, hiring a Hartford teacher to lead a basketball group and to start a current topics class one evening a week.

Her efforts were praised by the editor of the short-lived Farmington Maqazine, which extolled old village crafts and noted the fine work by Farmington's craftspeople - Hal Mason's cabinet work, Maud and Genevieve Cowles's stained glass windows, Florence Gay's leather work. Elbert Hubbard, the Roycrofter and disciple of William Morris, was invited to lecture on the value of crafts and manual training in the schools.⁵ This would be a very important tenet in the educational program Theodate would develop for Avon Old Farms some twenty-five years later.

Her charitable actions extended to other quarters. When a young woman who sold notions - ribbons, thread, needles - to Miss Porter's girls married, Theodate took over, intending both to raise money and at the same time provide a sympathetic refuge for the students. The proceeds were used to procure a visiting nurse for the town.⁶ Theodate opened her "Odd and End" shop in October of 1901 in the front room of the house she had added to the O'Rourkery. This house was known as the Gundy, after the school paper called the Salmagundi. Hot peanuts, tea, apples, gingerbread men, heart-shaped cookies and various notions, displayed in an old-fashioned case, were offered for cash, not credit, so a sign stated, explaining that the two good ladies in charge did not understand bookkeeping.

None of these activities once set in motion required her continual presence. Winters brought her to her parent's suite in the Buckingham Hotel in New York. Although she had always questioned the tenets of organized religion, she joined the least constrictive group, the Unitarians, attending the sermons and acquiring the books of Dr. Minot Savage.⁷ He attempted to apply Darwin's ideas to Christian ethics. So did Samuel D. McConnell, whose Evolution of Immortality Theodate read with interest.⁸ McConnell speculated that if a soul could survive death, it would be because that soul had perfected itself through a life of moral goodness and had built up a second indestructible brain or body capable of moving freely through ordinary matter. In 1898, a much more powerful thinker, William James, professor of psychology at Harvard, had taken up the issue of the possibility of the soul's immortality in Human Immortality: Two Supposed Objections to the Doctrine. This, too, Theodate read with fascination.

Many intellectuals thought that what was needed was scientific proof. A group of English scholars attempted to answer the question of the immortality of the soul by setting up scientific criteria to examine spiritual or psychic phenomena. Henry Sidgwick, professor of moral philosophy at Cambridge, aided by his wife Eleanor and several others, founded the Society for Psychical Research, the SPR, in 1882.⁹ William Frederic Henry Myers, a philosopher and classical scholar, who had been tutored by Sidgwick, became the Society's leading researcher until his death in 1901. The work of the Society offered the possibility of a reprieve from an overwhelming sense of an encroaching materialism brought on in part by new scientific discoveries. By the end of 1896, the SPR had over 900 members who were distinguished either academically, politically, or socially, including Alfred Lord Tennyson, Sir Arthur Conan Doyle, Sigmund Freud, Carl Jung, Henri Bergson, and Arthur Balfour (England's prime minister from 1902 - 5) who was one of Eleanor Sidgewick's brothers. William James, a corresponding member in 1884, organized an informal Boston branch the following year with Richard Hodgson as secretary. In two years its membership grew to over 400.¹⁰

Deciding to test the hypothesis that the dead might communicate by filtering through the brain of a medium, James, Myers, and Hodgson examined Mrs. William Piper in a series of séances over a twenty-year period beginning in Boston in 1885.¹¹ Hodgson, who had just denounced Madame Blavatsky, the founder of the Theosophists, as a fraud and Russian spy, had Mrs. Piper followed by detectives to ascertain whether she was secretly collecting information about her sitters.¹² Upon finding no evidence, he became an avid supporter, promoting her séances. She was invited to England in 1889 to be tested, with mixed results, by Myers and Sir Oliver Lodge, a professor of physics at the University College in Liverpool who had joined the SPR in 1884. Before his death in 1901, Myers would conclude that the séances had yielded contradictory and unsatisfactory results and that Mrs. Piper was nothing more than an "insipid Prophetess."¹³ Oliver Lodge, however, remained a firm believer. Undaunted, Mrs. Piper claimed that she was receiving messages from the deceased Myers in the form of automatic writing.

Theodate started reading the Proceedings of the SPR in September of 1900. She sought out back issues reading Hodgson's reports on Mrs. Piper with an intense interest which Mary Hillard shared. They both became members of the Society, and by 1904 Theodate had become well acquainted with the William Jameses and was participating in séances with Mrs. Piper. After Richard Hodgson's death on December 20, 1905, Mrs. Piper claimed that he was communicating with her. Asked to investigate by the SPR, James held seventy-five séances at some of which Theodate acted as the control.¹⁴

Theodate described several of these séances in her memoirs. Mrs. Piper, sitting at a card table with three pillows placed before her, would drop her head, entering into a deep trance. Then she would raise her right hand, making the sign of a cross as a signal to begin. A pencil would be placed between her fingers and she would begin writing as inspired by an imaginary amanuensis who called himself Rector. Theodate recalled Hodgson's first "spirit" appearance as follows:

I placed a pencil between her fingers, and her hand made one strong perpendicular line and then another. These two lines were then crossed by a horizontal line, thus forming an "H." The pencil made scratches all over the paper like a machine gone wild, but at the bottom of the page again became quiet and wrote "odgson" and the pencil dropped. I said: "Is this my friend?" and placed another pencil between the medium's fingers, and Rector's quiet writing was resumed. He wrote: "Peace, friends, it was he. He could not remain, he was choked."

This may be of interest some time, if and when survival is proven to be a fact. For myself, I am inclined to believe that it will never be proven in the same manner as two and two make four. I am inclined to think part must still rest upon faith....¹⁵

By 1906 James would claim that the Piper investigations "had begun to bore [him] to extinction."¹⁶ In "The Final Impressions of a Psychical Researcher," published in 1909, James would admit that after twenty-five years of reading about and witnessing psychical phenomena, he was no further enlightened than at the beginning.¹⁷ Theodate's interest abated not a whit. Quite to the contrary, she became increasingly involved. Having always been interested in the realm of the spiritual and believing herself to have an increased sensory awareness, she separated what she considered the intuitive activities of the soul from the mundane functions of the body. When the American branch re-formed under Professor James Hyslop of Columbia University in 1907, Theodate contributed five thousand dollars as one of three founding members. After her father died in 1913, she gave eight thousand dollars and began to take a more active role.¹⁸ What was important as far as her architecture was concerned were the contacts she formed. Well-heeled English members invited her to their homes, enlarging her base of English friends. Her growing admiration for England, both her friends there and England's architecture, would influence her own architectural style. Also some of the SPR members were educators who would help mold her ideas on education.

There was yet another factor in Theodate's life during this period. At thirty-three she became emotionally involved with a widowed doctor, Dr. Charles Dana, whose minimal responses were sufficient to keep her attentions ardent and her life miserable. Mary Hillard had hoped that Theodate might marry her brother, John, to whom Theodate was devoted as a sister can be to a brother; but he was ten years younger than she.¹⁹ There was also a brief infatuation which flared up between Theodate and a young woman. On learning of Theodate's wayward heart, Mary Hillard was aghast that her protégé was slipping from her grasp. In December 1902 she took a year's leave of absence, moving into the O'Rourkery, but taking meals with Theodate at Hill-Stead.

Mary Hillard had been quite successful at St. Margaret's, but as the building became crowded and hemmed in by the encroaching industrialization of Waterbury, she wanted to move. As St. Margaret's could not leave the limits of Waterbury, she thought of becoming headmistress of another school. She also wanted to mull over the possibility of starting a new school. On February seventh Mary Hillard set sail for France with Theodate in tow. Ostensibly they wished to study French and the history and literature of France.

After a "horrid" crossing, they visited Mary Cassatt in Paris before heading south to Tours and the Convent of the Soeurs de Saint-Augustin. The Popes had met Mary Cassatt at the Whittemores in Naugatuck in 1898 when she had made one of her rare trips to the United States. On that occasion Cassatt attended an exhibition of her works at Durand-Ruel in New York and painted some portraits, including some commissioned by the Whittemore family. After that, the Popes visited her on their trips to Europe, and Theodate, especially, formed a close friendship with this grande dame of the Impressionists. The three women shared multiple interests, including spiritualism and women's rights, which brought them together not only in Paris but also at the painter's country house, the Château de Mesnil-Beaufresne.

There was one cataclysmic divergence of opinion between Theodate and Mary Cassatt which led to the artist's spilling her indignation into her correspondence with both Mrs. Pope and Mrs. Havemeyer, as well as with Theodate herself.²⁰ Theodate, never one to be deferential and in the habit of playing the devil's advocate, took the socialist point of view that paintings were isolated objects conveying many layers of meaning and that they should not rest in private hands but hang in public collections. Mary Cassatt, who was aiding the Havemeyers, Harris Whittemore, and other Americans to form their collections, was incensed. Yet there was more to Theodate's attitude than a budding socialist conviction that paintings should be for everyone. She opted for the bare walls of the Arts and Crafts aesthetic - the rooms themselves must be pictures.²¹

One also learns from Mary Cassatt's letters to Theodate that the two younger women sought out picturesque villages and visited the medium Madame Ley Fontvielle in Paris before joining Mr. and Mrs. Pope in London. Most important from the standpoint of the careers of Mary Hillard and Theodate was their decision that the former would head a new school designed by the latter. And just as she had designed the farmhouse that became Hill-Stead on her first grand tour, so Theodate spent much of her time on plans for Mary Hillard's school during their stay in France.²²

Since the school did not materialize for several years, this left Mary Hillard and Theodate picking up the threads of their lives where they had left off. Mary Hillard was back at St. Margaret's. Theodate continued to supervise her cooking and sewing school in Farmington, to assist at the Piper sittings with William James in Boston, and to see Dr. Dana in New York. She also joined the Henry Street Settlement as a nonresident following the lead of her school friends Alice and Agnes Hamilton who joined, respectively, Hull House in Chicago and the Lighthouse in Philadelphia. Lillian Wald, who started the Henry Street Settlement in the last decade of the nineteenth century, was the same age as Theodate though from a totally different background. Profoundly moved by the suffering of the hordes of poor immigrants on New York's lower east side, Wald had decided to put her skills as a trained nurse in their service and had found both a sponsor and another nurse to take up her cause. Besides making rounds from one dingy tenement to another, the nurses gave instruction in hygiene.

As other women rallied to her project, a morning kindergarten, cooking and sewing classes, and boys and girls clubs were organized in a three-story house Lillian Wald acquired at 265 Henry Street.²³ It was to the latter activities that Theodate's experience in Farmington proved valuable. In return, the experience of working with independent feminists fanned Theodate's socialist inclinations. One doesn't know when she first became involved, but she was clearly there in 1906, and she probably continued intermittently through 1910 at least.²⁴

It was finally decided to build Hillard's school in 1906. Occupied as she was by her charitable activities and the SPR, Theodate might not have undertaken any other major architectural projects if it had not been for Mary Hillard. John H. Whittemore, who had commissioned two schools for Naugatuck, was interested in what he could do to enhance Middlebury, a quiet country village near his summer farm. As Middlebury seemed like an ideal location for a school, being about five miles west of Waterbury, Whittemore secured an option on a tract of approximately one hundred acres on one side of the town green. Together John Whittemore and Alfred Pope, who was grateful to see his daughter get another opportunity to test her architectural skills, underwrote the land and construction costs, which were to be recovered by the sale of stock - Whittemore becoming the chief stockholder. The school was named Westover after its location as west over the hills from Waterbury.

Early in February 1907, Theodate had completed the plans to show Mr. Whittemore.²⁵ Although McKim, Mead & White had taken charge of the new north study being added to Hill-Stead at this time, the firm was not consulted for the school, and Theodate found her own draftsmen in New York. By the end of June the foundations of the building had been staked out and the elevations were being drawn up.²⁶ Richard Jones, who had pleased the Popes at Hill-Stead was again called in as contractor. Later, in 1909, Warren Manning was commissioned by Whittemore to convert Westover's acreage into school grounds.²⁷

Westover was planned to face the south side of the Middlebury common. Directly across the green, once shaded by large elms, stood the white clapboard Congregational church. Built in 1840, its Greek Revival characteristics set the architectural tone for the neighboring houses. The green already had a clutch of churches. A Greek Revival Methodist church at the southeast end eventually was taken over by Westover for lack of worshippers. A Catholic church, built between 1907 and 1914, was added at the southwest end. This is a curious cobblestone building with two cobblestone towers. Yet, in harmony with the Congregational church and the town hall, there is a pedimented gable supported by Ionic columns. Flanking the Congregational church is a Georgian Revival town hall, its red bricks adding a touch of color.²⁸ A store, a blacksmith shop, and a school were relocated to accommodate Westover, and a trolley was extended from Waterbury to bring out the workers.

To maintain harmony with the other buildings on the green, Theodate chose a Colonial Revival idiom. A clapboard building would have been impractical because of the danger of fire. So Westover was constructed of lathing and cement and is covered by a cream colored stucco. Dark green shutters frame the second story windows creating a horizontal accent. Like the facade of the "Wren" Building of the College of William and Mary, which Theodate had seen when she visited Williamsburg, there is a gabled central entrance pavilion with a cupola rising from the roof (Figs.26, 27).²⁹

Westover is a very large building. Its facade is 270 feet long, twice the length of William and Mary's "Wren" Building. That a feeling of intimacy is projected is largely a question of proportions. And it was just this refinement of proportions which Cass Gilbert praised when he wrote in 1912 that Westover was the best girls school he knew of in America (from an architectural point of view).³⁰ A major difference between the facade of Westover and that of the College of William and Mary as well as a whole tradition of eighteenth-century eastern colleges is that Theodate's roof is much steeper, absorbing a large portion of the upper section - not only the third story but also the attic.³¹ Visually the height of the roof is greater than the height of the first two stories. Steep roofs were associated with domestic, not public buildings and they would become a characteristic feature of Theodate's country houses.

Bracketed overhanging gables are found in English vernacular timber framed houses. The effect of the projecting gable of Westover's central pavilion is of a house within a structure, which conveys a sense of home rather than institution to the entrance (Fig.28). The gable is personalized by the school's coat of arms molded in high relief. An escutcheon with three roses, surmounted by a Roman lamp resting on a book, is displayed between a flourish of acanthus leaves. Unfurled on a scroll below, a motto, cogitare, agere, esse (To Think, To Lead, To Be), proclaims the students' goals.³² Above the gable rises a hexagonal cupola containing a large seventeenth-century bell, which called the girls to meals and chapel.

Above all Theodate wished to create a school which did not look institutional and in which the girls could feel at home. She succeeded partly because the proportions of the facade are on a human scale and partly because there are two wings which project at the east and west ends as if reaching out to embrace the visitor. The prominent placement of these wings reflects the nature of the school. The west wing contained Mary Hillard's quarters with its entrance facing east. Her authoritarian personality stamped her vision indelibly upon the school. The east wing comprises a chapel with its porch also facing inwards (Fig.29). Mary Hillard considered maintaining religious traditions an important factor in the nurturing of school spirit. Wishing to differentiate the chapel from the rest of the school because of its special function, Theodate chose a Gothic style that from the time of Pugin and Ruskin had been seen as a style of moral perfection best suited for a church. Although there is a general effect of symmetry, the chapel has visual weight because it projects beyond the headmistress's wing. The overall effect is one of beauty, simplicity, dignity, and order - qualities that Mary Hillard meant to instill in her girls.

Eschewing a cluster of buildings, Theodate, having long admired the Oxford and Cambridge colleges, chose a cloistered quadrangle so that everything could be united under one roof to achieve a greater sense of community. Yet there is nothing medieval in the style of the broad elliptical arches of the arcade that shelter all but the central hall in the courtyard. The ground level of the rear of the quadrangle is lower than that of the courtyard in order to expose the basement windows. A grassy mound, with red sandstone steps at the center and shallow stepped brick ramps at the sides, leads from the athletic field to the courtyard through the Sally Port. At the apex of the roof of this porch, Theodate, who delighted in the unexpected, whimsically placed a miniature building. Perhaps this was a reference to old- fashioned country barns where one occasionally finds a building substituted for a ventilation cupola or a ramp leading to the second story where the hay is stacked.

The interior of Westover is in some ways even more interesting than the exterior. Having chosen a quadrangle, an innovation for a private school at that time, all the functions of the school were collected within a single building. There was a post office and a shop off a wide corridor that gave access to reception rooms and offices and led to the chapel. The east side included dining rooms and a kitchen, above which were a two-storied gymnasium and a dormitory. To the right of the main entrance is a large rectangular hall that was used for such functions as receptions for guest speakers. Red Hall still has some of its original furnishings: fringed red lamps standing on oval tables and a red carpet duplicating the worn-out original. The rectangular room is elegant in a modern sense. No heavy curtains distract one from the clean proportions marked out by the dark beams against the bare white walls.³³ Piers supporting a balcony and beams extending across the ceiling mark off the room into square or rectangular segments. There are no soft curving forms; a grand staircase to the balcony angles off to the left and right. This same sparse Arts and Crafts aesthetic also governs the dining room in the eastern wing of the quadrangle. The school's first catalogue states that "the building was intentionally kept free from luxury as unsuited to school life and out of harmony with the atmosphere of the village, and the quiet refinement which goes with straightforward simplicity."³⁴ The west side of the quadrangle contained a library, classrooms, a studio, and a study hall.

The chapel, which was dedicated to St. Margaret in honor of the parent school in Waterbury, is reached from the interior at the east end of the spacious hall which runs perpendicular to the main entrance. The door, leading into the chapel, suggests an Arts and Crafts sensibility with two rows of square windows for viewing and long, handmade hinges. The cream colored interior is bathed by clear light pouring through windows decorated with patterns of streamlined Gothic tracery. Because the pointed chancel window above the altar is taller than the arched chancel opening, the effect from the nave is that of a luminous grandeur within the sanctuary (Fig.30). At Easter the scent of white lilies would have increased one's sensory delight.

The school opened for spring term on April 27, 1909. Mary Hillard managed to bring with her from St. Margaret's one hundred and thirty-five boarders and much of her staff. What made Westover special, apart from its sound academic instruction, was its emphasis on school spirit.³⁵ By binding the student to school rituals, Mary Hillard thought she could best instill such values as truth, honor, love, selflessness, courage, patience, and justice - virtues with which the girls could ameliorate a materialistic and industrialized world. School traditions were also meant to help prepare the girls for the "ritual of life."³⁶

One of the first traditions created was St. Theodate's day. On the morning of May 21st, less than a month after the school opened, Theodate appeared for breakfast at 7:30, having been chauffeured over from Farmington, and asked for a holiday to be named after her. Mary Hillard, who welcomed changes from routine, agreed as long as she came in person on that day and in the same way. Mary Hillard was less than pleased when, on one such occasion, Theodate gave her dog, dusty from the ride, a bath in the headmistress's tub. This incident left the two women not speaking to one another for some time. A more lasting tradition was the Lantern Picnic. The week before school ended in the spring, students gathered around a bonfire at dusk, each graduating senior receiving light for her lantern from the headmistress. Singing, they wound their way back to the school, to the balcony of Red Hall and a culminating "Auld Lang Syne." Guest speakers appeared regularly including John Masefield, Poet Laureate of England, and Dr. Wilfred Grenfeld, founder of the Labrador Mission. There were also societies formed, like Dorcas, which performed community service.

Although Westover was not a church school as was St. Margaret's, many of the traditions created were religious in order to make religion an important part of the students' lives. Because the chapel was dedicated but not consecrated, the students of all religious sects came to the Episcopalian services held twice a day in the morning and evening, and to a single evening service on Sunday. The delicate voices of the girls singing, as they entered, commenced morning chapel. The 23rd Psalm was always sung on Sunday evening; on the evening of Good Friday Mary Hillard read the life of Christ from the Gospel of St. Luke in Red Hall. None of Mary Hillard's efforts to bond the students to the school were lost on Theodate who would attempt to do the same, albeit in a different manner, later at Avon Old Farms.

Westover was not Theodate's only architectural endeavor at this time. She had a studio for her various projects where she met her draftsmen and worked on plans. This was Underledge, a fieldstone cottage built by William Potts who had sold it with eight acres to Alfred Pope in 1898. By 1907 when the Popes had acquired at least one car, Theodate had designed a combination garage and gardener's workroom adjacent to the Hill-Stead barn complex (Fig.31). Its proximity to the fieldstone wall of the sunken garden gave her an opportunity to deviate from the Colonial Revival appearance of Hill-Stead's house and barns. She chose fieldstone walls that convey an Arts and Crafts sensibility. The gables are filled in with white clapboards of uneven widths like the barns.

In June 1907, when she was finishing the Westover elevations, Theodate was also restoring a large brick Federal house she had bought at 130 Main Street in Farmington. She had meant to turn it into an exclusive inn for motorists, but the idea was trounced by her father. The house had been built for a member of the prominent Cowles family and had eventually been home to a generation of artistic Cowles sisters. Two of these, Maude and Genevieve, created stained glass windows and illustrated books. After Maude died in 1905 and Genevieve went off to Jerusalem as preparation for a mural for the State Prison chapel in Wethersfield, Connecticut, it was thought best to sell the house.³⁷ The top floor had been originally designed as a ballroom. And it was here, perhaps to celebrate the completion of Westover, that Theodate gave a lively supper party with champagne flowing and clog dancing to a seven-piece orchestra.