The Cherry Pit, however, did not always encompass such a large area. The first Cherry Pit was a few sheets of paper tied together, and filled with stories and articles which had little to do with the school. Each article was handwritten by the author, crudely illustrated, assembled, and then hectographed, with lines running together, "t's" not crossed, and misspellings not corrected. For a few years after that, the Cherry Pit showed great improvements. It was printed or at least mimeographed. It expanded far out of the field of pure literature, as it contained articles on the Student Government, the faculty, the students, school drama and activities, as well as student stories and articles. Of course, sports were notably represented as was the "Last Will and Testament" feature.
In 1926, the Cherry Pit began to place more emphasis on the graduating class. In that year there was another innovation: aside from the June issue, there were two other issues of the Cherry Pit as well. In the following years, the Cherry Pit continued on approximately the same pattern: one formal issue, and two or three other issues in preparation, as it were, for the formal June issue. As a rule, these preliminary issues contained little factual material, but were usually completely artistic and literary. The Cherry Pit, then, was a small magazine, written by and intended for the students. It was a product of themselves, a token to remind them of their thoughts, their hopes, and their lives at Cherry Lawn after they left. It was Cherry Lawn on paper. There were, of course, no advertisements as the magazine was too small for such a thing.
As the years went by the Cherry Pit became thicker. It was not only about the school, but the school's views on various subjects. For example, the 1939 issue was devoted in large part to world conditions and the possibility of war. This indeed was a new subject for the magazine. The following year, the subject of war kept recurring. The few light articles were not enough to hide the constant fact: Cherry Lawn and the Cherry Pit were becoming world, as well as school conscious.
In 1941, the Cherry Pit established another precedent: in the back of the magazine were advertisements, although only a few. In January, 1942, the aim of the Cherry Pit was changed from a publication of students' creative works to the "reflection of the time through the eyes of the students," as it says in the editorial of that issue. The theme that year was once more war.
The 1946 issue saw a new type of Cherry Pit: half yearbook and half literary magazine, all under one cover. This new Cherry Pit was no longer a magazine, but a hardcover book. It was an entrant at the Columbia Scholastic Press Association. In 1949, the Cherry Pit moved still another step further by winning second prize in its category in the Columbia Scholastic Press Association Yearbook competition.
The pattern established in the years following World War II became the basic model for the remainder of its existence. Nevertheless, as one reviews the issues over the years, it is obvious that they speak for their times. The standard studio graduation photo poses and hair styles of the 1940s and 1950s gave way to a new mood in the 1960s. Students now were photographed outdoors, in their car, or with guitar in hand, and Bob Dylan or Joan Baez was more likely to be quoted as a source of inspiration than Elinor Roosevelt or Ralph Waldo Emerson.
The last edition of the Cherry Pit appeared in June of 1972.