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.