By 1914, several Catholic immigrants or their sons had acquired considerable wealth . Examples include Henry O. Havemeyer, nephew of the sugar baron; Allan Ryan, the son of Thomas Foutune Ryan, a tobacco, insurance, and transportation magnate; Clarence Mackey, son of John Mackay, who had a net worth of $30 million investing in mining stocks and operating silver mines on the Comstock Lode when he died in 1902; and James A. Farrell, president of U.S. Steel from 1911 to 1932 and founder of the Isthmian Steamship Company. These titans of business and others provided the necessary financial backing to make Havemeyer’s dream to start a school operated by Catholic laymen who, independent of a religious order, would prepare boys for the best colleges and universities in the country while training them in their faith. His dream was bold, unique, and controversial. If planned for properly and brought to successful fruition, it would be the first school of its kind in the country.

This accumulation of wealth centered in New York City. New York’s large Catholic population consisted of the two prominent immigrant peoples of the time: the Germans and the Irish. These Catholic men had the financial foresight and wherewithal to wield their power and influence. Against the background of this potent academic, social, and financial background, the seed to establish Canterbury was planted.

In 1913, Henry O. Havemeyer hired Alexander “Alec” Hume, brother of Nelson Hume, to tutor his son, Henry Jr. Based on written correspondence between Alec and Mr. Havemeyer, the two had a professional and cordial relationship. Havemeyer wanted his son, Henry Jr., to enter Yale University, but what could potentially be the lad’s lack of religious formation prior to entering college concerned his father. The elder Havemeyer could have elected to send Henry to Hotchkiss, Taft, or Exeter, or any of the many established schools that prided themselves in preparing boys for the elite colleges. What specifically concerned Havemeyer was what might happen to his son’s Catholic faith at any of these schools.

Havemeyer, pleased with Alec’s success at tutoring Henry Jr., asked Alec if he would spearhead planning all the details inherent in founding a college preparatory school operated and taught by Catholic laymen. Although Alec felt confident filling in young Henry’s academic gaps, when asked by Mr. Havemeyer to start such a school, Alec reportedly retorted, “I’m not your man, but I have a brother.” Dr. Nelson Hume was brought on to steer the School this pivotal point in its history.

Dr. Nelson Hume had been on the faculty at two Catholic schools, Loyola School in New York City (1903) and The Newman School in Hackensack, NJ (1906), where he served as Assistant Headmaster from 1912-1913. His tenure at The Newman School was short. Ambitious and confident that he had the requisite experience, he left Newman to start his first school, which opened on September 24, 1906. Initially, Nelson called it School for Boys. However, in September 1908, the title Hume School appeared on the catalog cover and in the announcements. The Hume School prospered to such a degree that administrators at Newman and Hume Schools proposed and carried out a merger. The plan called for Nelson to become headmaster, but a clash of personalities between him and Newman’s Headmaster prevented this, and Hume withdrew from the venture. That experience caused him to reevaluate his place in the world of education. From 1913-1915, Hume had a brief career as an interior decorator with W.P. Nelson Company of Chicago and then as an assistant to the President of the New York Life Insurance Company. Unfulfilled by these jobs, Nelson was in a position to, once again, answer a call to a life in education.

In a handwritten letter dated September 28, 1914, Alec Hume reports to Havemeyer that he, Hume, had floated the idea of the kind of school that Havemeyer had in mind during the summer of 1914 to members of influential Newport families whose boys, he believed, created a “demand for the opening of a Catholic school which would provide for their education in the best possible way.” He adds, “Around the nucleus of these boys, I am certain that a Catholic school, that would eventually take its place with such schools as Groton and St. Mark’s, could gradually be developed, if a group formed of certain Catholic men would agree to take an active role in supporting the efforts of an accomplished headmaster.”

Impressed with Nelson’s school experience, Havemeyer agreed to meet Nelson and arrange an introduction for Nelson to meet Clarence H. Mackay, President of the Postal Telegraph Company. According to David Hume ’45, Nelson’s son, “That introduction was the key to the formation of Canterbury School and, because of his role in it, Henry O. Havemeyer later claimed, with some justification, that he founded Canterbury.”

In addition to the letter of introduction he had written for Hume to meet with Mackay, Havemeyer stated in a letter to Mackay, “A proposition has been presented to me for the establishment of a first-class preparatory Catholic school for Catholic boys, on the lines of the well-known Groton, St. Paul [sic] and Andover, etc., where they can be brought up in their religion, at the same time meet men that they will associate with in after years. The establishment of such a school I feel is most imperative.”

David Hume penned in the memoir he wrote on the occasion of his father’s 100th year: “Mackay and Hume met at Mackay’s office at Postal Telegraph. Mackay asked of Hume, “What was it you wanted to see me about?” Hume responded, “Mr. Mackay, I want to start a Catholic school that no one will have to apologize for.” To which Mackay said, “That’s a wonderful idea. How much money do you want?” Mackay’s optimism and generosity “proved to be the perfect complement to Hume’s energy and idealism.”

After Henry Havemeyer and Nelson Hume met, Havemeyer found Hume to be the ideal person for starting “his” school. Mackay concurred and later assured Havemeyer of his interest, writing on March 13, 1915, “I had a most interesting interview with Mr. Hume yesterday at my office, and was very favorably impressed with his general ideas on education. Mr. Hume is an enthusiast on his subject and if energy counts for anything, I should judge that he would make the proposition a go.”

In searching for a campus for Havemeyer’s proposed boarding school, Hume desired a location that was close enough to New York City to attract wealthy Catholic boys to enroll, but sufficiently removed to ensure a rural setting, which he regarded as a major selling point to prospective families. He visited many of the existing prep schools, made congenial acquaintances among his prospective colleagues, and concerned himself with such practical details as railroad service, water supply, and available land. In addition, he drove many miles through the towns of Northwest Connecticut and had almost concluded that the town of Litchfield would be an ideal place, when he learned that the land and buildings of the recently closed Ingleside School for Girls were for sale. He approached New Milford from the north, reached the crest of the dirt road, past the Elkington Farm, and looked west into the Housatonic Valley. His gaze took in 12 acres and three major buildings, the imposing Weantinaug Hall, the cozy, lodge-like Bungalow, and a small structure that housed servants. He knew immediately that he had found the right place.

The site also contained a large playing field, shaded walks, and an elegant fringe of tall elm trees. The Ingleside School was started by Sarah Sanford Black in 1892. Mrs. Black located her school on Elm Street, in the building that now houses the offices and CCD classrooms for St. Francis Xavier parish. When it opened in 1892, Ingleside School for Girls prospered. Encouraged by its success and eager to build upon her financial good fortune, Mrs. Black opened a boys’ side to Ingleside in 1901 with the financial assistance of her sister Caroline. For that purpose, she erected Weantinaug Hall on the top of Aspetuck Avenue, naming the Hall after the local tribe of Indians. When Weantinaug Hall came under control of Canterbury, it became known as Main House and contained classrooms, student rooms, the dining room, and offices. The large half-timbered structure occupied the site of what is now the parking lot in front of Sheehan House. She also had built the Bungalow, a residence for her students. To add to her hilltop campus, Mrs. Black purchased a small building from the defunct Adelphic Institute, a boys’ school that had closed in 1880, and ordered the building moved from its original site on Chicken Hill to its present position to the north of Sheehan House. That building, greatly renovated and expanded, is now the Chaplain’s residence and the oldest building on Canterbury’s campus. Mrs. Black first used it as a residence for the servants of Weantinaug Hall. Later, it served as her school’s gymnasium and Canterbury’s first chapel. Mrs. Black abandoned the boys’ school venture in 1904, and the Girls’ School took over the buildings before Dr. Nelson Hume came along. 

By April 1915, the financial foundation and location for the School was in place, and Canterbury School, Inc. was formed under the laws of Delaware. The first stockholders consisted of Henry O. Havemeyer, Allan A. Ryan, John D. Ryan, James A. Farrell, Clarence Mackay, James H. Ward, Nelson Hume, Condé B. Pallen, and Cabot Ward. On June 19, 1915, Hume arrived in New Milford to take formal possession of the grounds and buildings the corporation had leased there as he then tried to secure his first students at the school.  

Not only was Hume to serve as Canterbury’s headmaster, but he was also, out of necessity, to serve as its first Director of Admission and all matter of additional roles typically associated with the running of a prep school. He took to the road, travelling by car and rail to convince parents to send their son or sons to the School. In addition to drumming up business in the tri-state area, he met with families in St. Paul, Milwaukee, Chicago, and St. Louis, to name a few.

The first boy to officially enroll at Canterbury was Cyril Clemens, Mark Twain’s distant cousin. Next to enroll was Henry Havemeyer’s son, Henry. The remainder of the “charter” students included John Crimmins, James Farrell, Jr., Joseph Graham, Cyril Hume (Nelson’s youngest brother), Joseph Kelley, Peter Maloney, Nicholas Nelson, Richard and Swithin Nichols, Thomas Pallen, Allan and Theodore Ryan, George Saportas, and Charles Ward. Two more boys, Edward Carmody and Lambert Borden, joined the ranks in October, and, at mid-term, two additional boys, Charles Martin and Grosvenor Fessenden, enrolled. However, the 18 enrolled in the fall of 1915 are generally considered Canterbury’s charter students.

On June 16, 1915, the Executive Committee of Canterbury School met in the office of Clarence H. Mackay to review the qualifications of the masters who Hume desired to hire. The proposed faculty for the first year included Alexander Hume (teacher of the lower form boys, business manager, and confidential assistant to the Headmaster), Maximillian von der Porten, Ph.D. (teacher of French and German), Patrick J. Downing, Ph.D. (teacher of Latin, Greek, and History), James J. McCarthy (Latin), and Frank J. Rooney, M.A. (teacher of mathematics and science). The Committee approved them all.

All the moving parts, the Canterbury idea, sufficient funds, an ideal property, a faculty and staff, and enrolled boys, had finally come into place. A memo dated June 7, 1915, states that the School would open on September 23, 1915. For reasons unknown, Canterbury opened exactly one week later, September 30, 1915. The same memo also states that there would be seven “classes” (Forms), three years of grammar school (Pre-Form, First Form, and Second Form) and four years of high school (Forms III-VI), “from which its scholars would enter college.” According to School documents, the Trustees set tuition at $800 for lower form boys and $1,000 for upper form boys.

Ever attentive to details and by now willing to make some decisions independently of Havemeyer, Hume selected navy blue and Columbia blue to be Canterbury’s school colors, although Havemeyer’s preference was navy blue and white. Hume found his combination to be pleasing to his own eyes, and his choice was abetted by the fact that these colors were also those of the Blessed Virgin Mary.

With the matter of school colors determined, Hume then went about the business of selecting a School motto. Because he believed that his prayers to St. Jude had had some efficacy in the establishment of Canterbury, he found, in the Introduction to the Epistle of Jude, the Apostle, these words: “Beloved, when I gave all diligence to write unto you of the common salvation, it was needful for me to write unto you, and exhort you that ye should earnestly contend for the faith which was once delivered to the saints.” Thus, Supercertari semel traditae sanctis fidei–to fight valiantly for the faith once delivered to the saints–became the expression of Canterbury’s mission.

Within two years of its conception, Canterbury was a going concern. It had a beautiful location, a serviceable plant, some working capital, an energetic headmaster, an excellent faculty, 18 students, and a bright future.