Horace Dutton Taft got his start in 1890 as a schoolmaster when he was invited by a family friend, Mrs. Robert Black, to head a brand new college preparatory school for boys in Pelham Manor, New York. Until then Taft’s experience as an educator had been limited to tutoring Latin at Yale, his alma mater. Here, presented with 17 students of “extraordinary variety for how few they were,” Horace Taft plunged headlong into the complete education of the boy, and indeed his own as a headmaster. Mrs. Black named the small institution “Mr. Taft’s School.”

Pelham Manor
Often noted for his warmth, humanity, and sense of humor, Horace Taft described the first years at Pelham Manor: “It was a most comical beginning of a school. The furniture arrived at the same time the boys and their parents did, and I put both to work on the front porch opening boxes. Carpenters were at work upstairs, putting up the beds. Mr. Black was there, and he was moving around, entertaining parents and boys. Considering how few they were (seventeen), there was an extraordinary variety among the boys. An undue proportion of them had been in other boarding schools and knew more about the inside of one than I did.” As he would for the rest of his career as a headmaster, Horace embraced the education of the whole boy, and in true boarding school fashion, got a dose of the same experience himself. In addition to managing the school, Mr. Taft taught Latin and mathematics, and lived the 24-hour job of dormitory master.

“Discipline was primitive and direct. I had a room in the middle of the house on the second floor, and I could reach almost any boy. I waked the boys up in the morning, pulling the blankets off when necessary. There ought to have been a Mark Twain there to describe that school.” He soon cultivated what would become his life-long calling as a headmaster: “One thing cheered me mightily. I suppose that nothing pleased me so much in my plan for a boys’ school as the idea that I might be a lay preacher, that association with boys would give me opportunity for influencing their ideas and ideals. In my stay at Pelham Manor I learned a great deal about a headmaster’s work, even if a large part of it consisted of learning how not to do it.”
At the end of his second year at Pelham Manor, Horace married Winifred Thompson, a teacher at New Haven High School. By then he had decided to find a location for his school farther from New York City. In 1893 the young couple moved the fledgling school to Watertown, Connecticut.

Why Watertown?
The Tafts had been introduced to western Connecticut during visits to a friend in Litchfield. For a while they were determined to locate there, and seriously considered three possible sites. In the meantime, word of their search for a ready-made facility had gotten out. It ended in March 1893 when an acquaintance from Yale offered his family’s hotel, which stood languishing in a place called Watertown. Wasting no time, Horace and “Winnie” spent a frigid day inspecting the 30-year-old Victorian ark called The Warren House. It was, in Taft’s words, “a forsaken place,” cold and dirty. Despite “the chill of the visit” the young couple decided to lease the building and its six acres with an option to purchase the property in five years. The Tafts quickly realized that Watertown was more accessible to New Haven and Waterbury than Litchfield, and felt immediately welcomed by the community. Thus, with a $10,000 loan, they set about refurbishing the great old building. With the exception of the tremendous disparity between the room sizes, oft-mentioned parental fears about the “Firetrap,” and well water of dubious quality for drinking, the property seemed to the Tafts like “Paradise” after Pelham Manor, and served the fledgling school adequately for the next two decades.
The Taft School, Watertown
Mr. Taft’s School opened in the fall of 1893 in the Warren House, a large, drafty old structure which had seen better days as a hotel. There were five masters, 30 boarders, and a handful of day students. Latin, mathematics, English, history, and science comprised the curriculum, with Greek and modern languages (French and German) offered additionally to the older classes. Early on, Mr. Taft instituted the monitorial system as a way of teaching responsibility and introducing student self-governance. In 1898 he changed the name of the five-year-old enterprise to The Taft School.

In his early school catalogs, Taft touted Watertown’s “clear, dry, and bracing air” and made clear his expectation that the boys would “take vigorous part in athletics.” The Warren House property included some very wet fields for the first football and baseball games played against the Gunnery, Hopkins Grammar and other area schools. The first track teams competed on a horse race track which dated from the hotel’s early days. There was informal amusement, too, for boys and grown men alike. Old photographs reveal Horace joining in baseball games and sledding sessions down the Green Hill and into town. Although he was revered as the embodiment of all the school stood for—character, intellect, hard work—this consummately dignified headmaster was also beloved for his humanity and sense of humor. His students called him “The King.”