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.