In late February of 1866 young Cheshire left home for Hartford. An inexperienced boy, having traveled little beyond his section of the state, he now set out to enter a strange school among people with whom, less than a year ago, his people had been at war. Such a prospect would have filled an older heart with trepidation. He traveled as far as New York with a stranger who had been in Tarboro on business, and from thence he went alone to Hartford.

Cheshire was allowed to enter the Freshman class with conditions only in Greek and Latin composition, which was a tribute to the work done under Mr. Wilkinson that fall. He learned upon arriving at school that he was the first man from the Confederate States to enter Trinity since the close of the war. He was treated kindly by his fellow students, and never complained of any hostility or unfriendliness on the part of the northern boys. His closest friends, however, were among a group of students from Maryland.

Shortly after he entered college, his father wrote to President Kerfoot asking him to suggest someone on the faculty who would be willing to act as an advisor and friend to his son. Dr. Kerfoot proposed Rev. William W. Niles, Professor of Latin at Trinity, who gladly took Cheshire under his care. In time the two became fast friends. Professor Niles and his wife often entertained him and always made him feel at home in their house. Under Professor Niles' direction Cheshire was prepared for confirmation, and in May, 1866, he was confirmed in the college chapel. In later years he said of the Nileses: "I can never be sufficiently grateful to Professor Niles and his good wife.... I enjoyed from that time—from my Freshman days in college to the end of their lives, the friendship and confidence of these most admirable people."[3]

Dr. Cheshire had a good deal of difficulty in maintaining his son at college. The years immediately following the war were hard ones for almost all southerners, and the Cheshire family was no exception. When Cheshire came home for the Christmas holidays of 1867, his father told him that he would be unable to send him back to college. He accepted this decision as final, and wrote his roommate, Robert F. Bixby, that he was not returning to college after the holidays. Not long afterwards, Dr. Cheshire received a letter from Professor Pynchon, a member of the Trinity faculty, who informed him that a friend, who wished to withhold his name, would be happy to advance the necessary money for his son's monthly board if that would be sufficient to make his return to college possible. After talking the matter over with his son, Dr. Cheshire accepted the generous offer, since he believed he would be able to repay the full amount by the end of 1868. In this way young Cheshire was able to resume his work at Trinity, receiving each month through Dr. Pynchon the money for his board. As he had anticipated, Dr. Cheshire was able to repay the whole debt at the end of 1868. Although he never knew, Cheshire suspected that the money, so badly needed at the time, came from the father of his friend, Robert Bixby.

During his first two years at Trinity, Cheshire had come to know Rev. John Williams, Bishop of Connecticut and one-time Presiding Bishop of the Episcopal Church, who often visited the college. When school closed in June, 1868, Cheshire found that he was not financially able to go home for the summer vacation, and that he would have to remain in Hartford. Bishop Williams heard of his plans and thereupon invited him to his old home in Deerfield, Massachusetts, for a month. The Bishop said that he could serve as his secretary, and on this condition Cheshire gladly accepted the invitation. As it turned out, he had very little to do. He spent the month most delightfully, meeting many interesting people and visiting near-by historical places. After leaving Bishop Williams, he spent a pleasant month in Maryland visiting two of his college friends. Thus most of the summer passed rapidly, and he returned to Hartford greatly refreshed, ready to begin the last year of his collegiate work.

While at Trinity Cheshire became a member of the Phi Kappa fraternity, now the Alpha Delta Phi. He was the only member of his class who belonged to this fraternity. Consequently, Cheshire modestly explains, whenever an honor fell to a Phi Kappa of his class he was the only one to receive it. Whether this was the reason or not, he was made president of the Senior class, and was elected a marshal for the commencement of 1868. As for class and college prizes, he never entered a contest until his last year. At this time he entered the competition for the "Tuttle Prize," which was an award of thirty dollars for the best essay by a senior on a subject to be chosen by the faculty. The topic selected for Cheshire's class was "The Causes of the French Revolution." Cheshire submitted a paper of forty-eight foolscap pages. Much to his gratification, and somewhat to his surprise, his essay won the prize. With the money he purchased "Pratt's Complete Works of Bishop Hall" in ten volumes as a gift for his father. For himself he bought a set of Chaucer's works in eight volumes and a few other books. Indeed, he seems to have made his prize money go far and to much advantage.

In June, 1869, Cheshire's college days came to a close. During his three and one-half years at Trinity he made many close friendships which continued throughout his life. He was not an outstanding student, but did creditably in all his courses. At the commencement exercises he delivered an original address, which was required of all graduates. He chose as the subject of his senior oration "The Strength of Republican Governments," a topic characteristic of that period. Cheshire had been influenced in the choice of this subject by De Tocqueville's Democracy in America, in which he had become interested. Following his graduation he returned to North Carolina, where he spent the summer of 1869 with his family at Monreath. This was his last long vacation. He was soon to take over his first position and to begin earning for the remainder of his life his own way.

In the course of graduation week at Trinity, Cheshire had the good fortune of making the acquaintance of Rev. John Avery Shepherd of Maryland. Dr. Shepherd had organized a few years before a private school, which he called St. Clement's Hall, at Ellicott City near Baltimore. Being favorably impressed with Cheshire's personality and his record at Trinity, Dr. Shepherd offered him a position in his school teaching Latin and Greek for the scholastic year 1869-70. His salary was to be six hundred dollars a year in addition to board and lodging. Cheshire gladly accepted the position, since he wished no longer to be a burden on his father. His younger brother was then ready to enter college and was only waiting for him to finish.

In the middle of September Cheshire left Monreath to take up his duties at St. Clement's Hall. Before he left home his father gave him fifty dollars to aid him until he should receive a part of his salary. This was the last time he ever gave him any money, that is, from a feeling of responsibility for his son's support.

At St. Clement's Cheshire was given all the upper classes in Latin and Greek, and in addition taught some arithmetic and algebra. In consequence of his rather poor beginning in Latin and Greek at the Tarboro Academy, he never became a scholar in these fields. While teaching Latin he became more interested in this subject and read rather widely in Tacitus and other Latin authors. In the course of his busy life of teaching he found time to continue "a kind of study" of Blackstone which he had begun in his senior year at Trinity. He also read through Kent's Commentaries and a good deal of English poetry.