The sixties began on a somber note for the Hewitt community. On June 25, 1961, Miss Hewitt passed away after suffering from a long illness. There had already been a growing sense of distance from the school—she wrote in 1957 that she had not visited campus since 1953. Her letters in the yearly Anchor newsletters of the fifties told stories of declining health and crippling arthritis. Her death prompted an outpouring of letters of adoration and appreciation from former students.

 

The school underwent various transformations during the sixties, a decade synonymous with change. A few months after Miss Hewitt’s passing, the administration changed the school’s name from Miss Hewitt’s to the Hewitt School. Many of the school’s founding teachers decided to retire, including The Venturer founder and English teacher Mrs. Beulah Riggs. Headmistress Comfort initiated steps to expand the campus. At the time, the lower school occupied the fourth and fifth floors of the Stillman Building. Assemblies and drama performances were held in the library, and physical education took place on the roof or in Central Park. With the purchase of the two-story building at 46 East 76th Street in 1964, the school expanded to include new science labs, art rooms, administration offices, a new boarding department, and a subterranean auditorium and gymnasium. When it opened in 1968, it was named the Gregory Building in honor of William Gregory, the school’s first board chair.

 

The decade saw the continuation and addition of many school traditions. Drama classes, the Christmas Pageant, the adoration of Glee Club, and Thanksgiving songs on the staircase continued. The 1960 publication of The Sparklet first mentioned the beloved “Turkey Song” tradition. One student reported: “The big surprise was the Kindergarten which came costumed in pilgrim hats made by themselves out of white paper bags. They sang ‘This is November’ and ‘Gobble, Gobble’ with appropriate gestures.”

 

To keep with the new styles and fashion trends of the sixties, the school decided to reexamine the school uniform. In 1963, after decades of the upper school blazer, Mrs. Comfort sought a change. Lower school students continued wearing jumpers as they had since the mid-fifties. The new upper school uniform consisted of plaid skirts with a kilt pin, a white blouse, and blazer. Students wore navy blue sweaters, stockings, or knee socks. Assistant Headmistress Miss Bradley, whose office was to the right of the front door, would shake hands with each student as she entered the building. Many alumnae admitted to adjusting their skirts before entering the school and rolling them after leaving. If Miss Bradley had doubts about appropriate coverage, she would ask the student to kneel down, and her skirt had to touch the floor. Mrs. Comfort extended the strict uniform regulations to rules concerning behavior. Unlike our current classroom dynamic, teachers did not encourage collaboration among students. Wendy Flink Levey, Class of ‘68, remembered the consequences of working on a translation of Caesar’s Commentarii de Bello Gallico with some classmates. A student had observed them discussing their translations in homeroom and reported it. Mrs. Comfort gave them all F’s in conduct for the whole of 10th grade. Wendy even had to step down as class president, an experience she later described as “very traumatic.”

 

The post-Kennedy political age, the war in Vietnam, and the political edge of popular music all inspired Hewitt students to follow current events more closely. Student publications began printing more opinion-based articles that encouraged classmates to observe the changing social landscape. The annual senior trip to Washington, D.C. appears as a yearly feature in The Sparklet. The school carefully organized the trips, often calling connected families in advance. Seniors of 1964 are photographed with Senator Edward Kennedy while another group in 1963 appears clustered around the desk of President Lyndon B. Johnson.

 

Keeping with their rebellious spirit, many students criticized and mocked traditional outlooks. In the 1969 winter edition of The Venturer, Amy Phillips Penn '69 satirizes the desire to sustain vanishing social customs of previous decades: "Today the era of finishing schools is clearly fading, slowly but surely. Were it not for the survival of dancing classes, holiday dances, and debutante parties, we would not be safe from the barbaric claws of the uncivilized. Clearly we are blessed. For some women are still adamant about their cause and will see to it that the elite institutions that still exist in our culture today will insure a better and happier world of tomorrow."

 

Hewitt students certainly found themselves thrust into a changing world. They would soon discover that their beloved “elite institutions” had no place in the seventies. Although the decade saw the advancement of the civil rights movement and second-wave feminism, Hewitt’s student body lacked diversity. Wendy Levey recalled: "None of the private schools in New York at that time really had any diversity. There were very few Jews in the schools, practically no African-Americans, very little diversity of any kind. And the first day of school was always on Rosh Hashanah or Yom Kippur—I mean, that was common."

 

In the sixties, diversity came only from international students, many of whom were visiting from countries such as Russia, Greece, and England. The school began to challenge the relatively homogenous school population in the eighties.

 

In response to changing demographics and educational priorities, the need arose for an admissions director. The pre-sixties admissions process had been managed by Mrs. Comfort and lower school head Mrs. Evarts. It included testing, but also relied heavily on administration’s instinct and connection to the prospective student. In the mid-sixties, the school appointed its first admissions director, a Hewitt parent named Lucy Littlefield. The new process involved a child and parent tour of the facilities together, a tradition still carried on today.

 

In 1968, her forty-third year at The Hewitt School, Mrs. Comfort decided to retire. Official notification came in a board letter of April 16, 1968, which announced her plan to step down the following June. She had seen the building development project through to completion and even celebrated the new facilities in her final Anchor letter in the fall of 1968. She assured parents that the school intended to remain small with a maximum enrollment of 275 students. In the spring of 1969, she welcomed her successor, Miss Janet Mayer, who would carry the school into yet another era of social and cultural revolution.

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