In the fall of 1861 Cheshire entered the Tarboro Male Academy, whose sole teacher at that time was Mr. Frank S. Wilkinson, a graduate of the University of North Carolina. In this school Wilkinson took boys of every age, from beginners to those preparing for college. Cheshire later tells us that Wilkinson was devoted to the profession of teaching, laboring "faithfully to interest his pupils, and give them the best that he had himself." The school usually numbered between thirty and thirty-five boys, but when it included as many as forty, Wilkinson engaged an assistant. During Cheshire's attendance at the Academy, Mr. William Henry Johnston was employed as an assistant. He was also a graduate of the University and, as Cheshire says, "a very good scholar after the standards of the day." In this small school, which never boasted more than two teachers at any one time, Joseph Cheshire prepared himself for college.

Since the summer climate of Tarboro did not agree with Dr. Cheshire's health, he purchased in 1850 a home in Franklin County, about four miles from Louisburg. This place was named Monreath and on it stood an old, well-built house surrounded by one hundred and sixty acres of land. Here the Cheshires spent their summers. These pleasant vacations at Monreath caused Joseph to lose about two months of school each year, since the fall term began the middle of July. Therefore, in the summer of 1864 he asked his father if he could not attend the Louisburg Academy from July to September. His father readily agreed, and each day young Cheshire walked the four miles into Louisburg to conjugate Latin verbs and pursue the other fields of learning which made up the curriculum of the average classical school of that day.

During the Civil War the Cheshires did not suffer from molestation by the enemy or from severe deprivation as did many southern families. They gave shelter and comfort to many refugees from the eastern part of the state, which was occupied by federal troops. Writing of his impressions of the war years, Cheshire observed: "It is strange that almost all my memories of those tragical days seem to be of bright and happy experiences. I do not remember any atmosphere of gloom or depression. The spirit of all was brave and buoyant."[1] The abolition of slavery did not greatly affect the economic status of his family, since his father owned only a few domestic servants whom he had inherited.

Cheshire's religious education began, of course, at home. Every Sunday afternoon he and his brother stood before their mother with the Negro children and repeated their assigned part of the catechism. He did not attend Sunday school until after he had learned all the catechism, that is, all but the "Desire." He later remarked that he never learned it "so as not to forget it," and that it was the only thing he ever tried to remember and failed.

By the fall of 1865 Cheshire was ready to enter college. It had been originally planned that he should go to the University of North Carolina. But when the time arrived his father did not have the money to send him. Dr. Cheshire, however, had already decided not to send his son to the state University; he did not think the environment there would be suitable for a boy of fifteen, for a good many young soldiers, fresh from the careless life of the army, were entering the University that fall. Cheshire's best friend, Dick Lewis, and several others of his class-mates went in the fall of 1865 to Mr. Graves' school in Granville County. He was left in a class by himself at the Tarboro Academy, where he continued his studies under the direction of Mr. Wilkinson.

During this period of study at the Academy Cheshire wrote an amusing and original essay on the subject of honesty. Launching into his subject with the statement that there had already been so much written upon it that it was about worn out, he declared that he chose the topic for want of a better one. This introduction was succeeded by the following:

"I have been thinking for a long time what else to say about 'Honesty,' but can't think of a single thing which some other boy has not said in his composition since I have been going to school: and I think that I had better practice what I have here attempted to preach, and tell you, Mr. Wilkinson, that it is Monday morning, and that composition never entered into my head Saturday, and so you need not expect much. Instead of a composition I will give you an account of my doings Saturday evening, which I hope you will take as an equivalent."

Cheshire then gave an interesting description of a delightful horseback ride he had had with a young lady. He concluded his essay by saying: "I hope this will be taken as a composition. If it is not I hope you will return it as there is enough clean paper on it to write another one."[2] The composition is not only worth quoting for its originality, but also because it brings out a pronounced characteristic of the later man. Complete honesty with himself as well as others, under all conditions, was one of his most outstanding qualities.

Joseph continued his studies under Mr. Wilkinson until February, 1866. By that time Dr. Cheshire had secured sufficient funds with which to send his son to college. He was still opposed to sending him to the University for the reason already mentioned and because he felt the fate of that institution at the time was most uncertain. He decided, therefore, to send Joseph to Trinity College at Hartford, Connecticut. Trinity was an excellent school, under the management of the church, and Dr. Cheshire was personally acquainted with its president.

Before his son left home for college, Dr. Cheshire told him that he must decide while in school what he wished to do for his life's work. He explained that since he had other children to educate, he would not be able to help him after graduation. His father went on to say that it would be a great happiness to him if his son should decide to go into the ministry, but that was something he must determine for himself. Cheshire later remarked that this was the only time in his memory that his father ever spoke to him of the possibility of making the ministry his life's work.