During a 1925 meeting, Miss Hewitt proposed a bold plan: sell the newly purchased townhouse in order to buy a “fireproof, modern school.” Despite the school’s “unequalled position, close to the Park and museums,” she felt it lacked necessary school facilities such as assembly rooms, a gymnasium, and science laboratories. Unfortunately, the patrons did not share her vision and preferred to retain the property. Miss Hewitt compromised by renting an apartment next door for use as a lecture hall, assembly room, and “an adequate stage where dramatic work can be given.” Then after two years, with parental support, she purchased the neighboring brownstones at 74 and 72 East 79th Street. The first of the two purchases housed the new upper school, and the second served as the “Assembly Room.” The original building, number 68, was rearranged to accommodate younger students. Despite increased space, the school had limitations, as former teacher Dorothy Brockway Osborne observed: "The school was crowded, the equipment inadequate, the plumbing limited to say the least. I don’t even remember where or how the students ate their lunch. There was no infirmary. If you were sick you went home…"

 

For all the difficulties, the school still persevered and continued to attract more students, many of whom found Miss Hewitt’s concern for the individual appealing. Although the school’s main campus had limitations, Miss Hewitt found ways to accommodate for all her girls’ needs. For example, since there was no space for a gymnasium, in 1927 the school opened an athletics center at the Young Women’s Christian Association on Lexington Avenue and 52nd Street. Early students certainly were fond of Hewitt’s early location, with its hominess and creaking carpeted stairs. Virginia French Pool, Class of ‘34, writes: "[There was] the wonderful element of surprise whereby you went home on Friday [and] never knew what you would find when you returned Monday morning; a door was suddenly there that hadn’t been, or a wall wasn’t there that had been. ‘Miss Hew’ would appear with a twinkle and say 'Well, they told us it couldn’t be done, but I knew it could…'"

 

Internal alterations to the school’s facilities were always performed over vacations, often without external visibility. Other alumnae accounts of the old building remember the charm of the bizarre location. Anne Bishop Cannon, Class of ‘43, wrote of “the steep stairs and drafty bathrooms, and the creaky little elevator that kept stopping between floors.”

 

As the prospect of war became more realistic in the late-thirties, the school undertook an initiative that would exist until the seventies: a boarding department. Initially housed in the neighboring building of Mrs. Virginia Ryan, the program provided homes, schooling, and safety for children from war-torn communities. Once the war was over and Miss Hewitt had taken a smaller role, it had become clear that, as the new headmistress Mrs. Comfort expressed in a 1950 memorandum, “only through moving to a modern building and incorporating can the future of the school be assured.”

 

As Miss Hewitt’s Classes entered the fifties, Mrs. Comfort sought to broadcast a message of growth and expansion to the intimate Hewitt community. In letters to alumnae in early issues of Anchor, Mrs. Comfort wrote of “changes which are always evidences of a growing school.” In the fall of 1950, Miss Hewitt’s Classes had arranged a contract with the heirs of Dr. Ernest Stillman and the sellers of a building at 45 East 75th Street. Erected in 1924-25 by Cross and Cross Architects, the neo-Federal building had been home to Dr. Ernest G. Stillman, a research staff member studying respiratory ailments at Rockefeller Institute Hospital, until his death in 1949. The building’s purchase pleased both parties: Dr. Stillman’s executors felt gratified to find a buyer willing to keep the building intact. Mrs. Comfort had found “the perfect building.” The school now had a beautiful library, a roof area for physical education, a backyard garden, and spacious classrooms that already possessed fire alarm systems.

 

Mrs. Comfort announced the actual moving day, June 5, in her alumnae letter in Anchor, 1951. She couldn’t help but praise the new campus: "A beautiful penthouse has been built for the four and five year olds. Also on the roof is a wire enclosure for outdoor gymnasium work. Many of who were able to come to ‘open house’ remember the large, airy, light-flooded classrooms and the lovely brick-walled gardens at the back of the house. I could go on and on!"

 

The new building looked very different in the fifties. There was no subterranean gymnasium, no stage or PAC. Drama productions were held at the far end of the library, where a raised platform was built. The lower school occupied the fourth floor and penthouse of the 75th Street building. By the early-sixties, assemblies and drama performances were still held in the library, and physical education took place on the roof or in Central Park. Recognizing the increasing student population, Mrs. Comfort initiated steps for another expansion.

 

In 1958, Hewitt purchased 44 East 76th Street, a brownstone that directly backed the 75th Street location. A courtyard garden behind each building served as the only connecting factor between the two buildings. For a few years, the new building housed the boarding department. The townhouse adjacent to number 44 was a similar brownstone, occupied by tenants paying modest rents. It took some planning, but in February of 1964 the school finalized the purchase of 46 East 75th Street. Miss Hewitt’s Classes now owned the mid-block area between 75th and 76th Street.

 

The board immediately began plans to demolish the old brownstones and introduce new classrooms, a new boarding department, and a subterranean auditorium/gymnasium. The new facility, which was only two stories at the time, would house the kindergarten and other classrooms. It was named the Gregory Building, honoring William Gregory, the school’s first board chair.

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