In his congregation Cheshire had some of the most distinguished members of the University faculty. President Battle was his senior warden and sincere friend, who gave him "judicious praise" as well as sound advice as to the pitfalls which a young clergyman might expect to encounter. Dr. J. de Berniere Hooper, Professor of Greek, was in Cheshire's opinion, "the most scholarly and highly cultivated" member of his parish. Professors Ralph Graves and George T. Winston, both young men who were later to win fame, were also members of his congregation. He lived on friendly relations with these and other members of the small faculty.

When Mrs. Cheshire came to Chapel Hill, she and her husband moved to the home of Dr. William P. Mallett, where they lived until the early part of 1879. They then took over the parish rectory, a small four-room house with a kitchen in the back yard. It faced Rosemary Lane and was situated on a two-acre lot, on part of which stands the present rectory. Their families and parishioners furnished the house for them quite comfortably. There was a small debt on the rectory, and, prior to Cheshire's coming to the parish, it had been rented to assist in retiring the obligation. When he moved into the rectory, he agreed to pay the interest on the debt, notwithstanding that his salary was only five hundred dollars a year. It was not easy, even in those days, to live on such a small income, but Cheshire often remarked that his years in Chapel Hill were "as happy, I believe, as possible in this world." He was fortunate in realizing his happiness at the time and often spoke of it to his wife. To make their happiness complete, a second child,[10] Elizabeth Toole, was born to them in the summer of 1879.

Although the parish in Chapel Hill was his chief charge, Cheshire did not think that it had an exclusive claim upon him. He regarded it as a center from which to work. In the fall of 1878 he began to lay definite plans for what was to be an important missionary work in Durham. After surveying the prospects there Cheshire, with the co-operation of his little flock, was able to rent a hall on Main Street which was ordinarily used for public entertainments. Here he held services on the first Sunday in every month. The work in Durham prospered remarkably, considering that the congregation had no church building of their own. Cheshire and his congregation soon realized, however, that if much progress was to be made, they must have a church. The greatest difficulty at first was to find a lot within their means. Finally, one was purchased at a low price because of its undesirability from a business standpoint. In the spring of 1880 the foundations of the little church were laid.

Since his congregation could bear only a small part of the cost of building a church, Cheshire had to ask for assistance elsewhere. His family and friends in Edgecombe County contributed about one-fourth of the total cost. In a communication to the Church Messenger Cheshire requested the rectors of the larger parishes of the Diocese to contribute one Sunday's offering to the completion of the Durham church. On the general subject of soliciting aid for religious purposes, he declared: "Indiscriminate begging from anybody and everybody to the neglect of every consideration, except the chance of getting a dollar, is not becoming to the cause of religion, and is a positive discouragement to Christian liberality." This was the kind of soliciting which he never practiced. Throughout his ministry he requested aid for the church of only those who he felt were rightfully responsible for its support.

By the spring of 1881 the church was completed at a cost of about twenty-five hundred dollars. In a remarkably short time, less than a year and a half, the money had been raised and the building erected. Cheshire named it "St. Philip, the Deacon," feeling it to be the "fruit" of his work as a deacon. It was with much pride and happiness that, on July 24, 1881, he assisted Bishop Lyman in the consecration of St. Philip's—a fitting close to his work in that mission.[11]

Cheshire never expected, nor did he ever receive, any compensation from the Diocese for his missionary activities. Concerning extra parochial work, he said: "I did not look upon work outside the parish as extra work, for which I should receive extra remuneration or special commendation."[12] Shortly after Cheshire began his work in Durham, the Treasurer of the Diocese sent him a check for twenty dollars, which he promptly returned, saying that he "did not desire to receive anything from the Diocesan Treasury."[13] During his three years of service in Durham the little mission paid him small amounts from time to time, which approximately covered the expenses he incurred. He looked upon his labors for this mission as "a pure work of love and missionary enterprise." In recalling this experience, he declared: "I believe I worked harder and with more enthusiasm in my Mission of St. Philip's, Durham, and afterwards in establishing St. Mark's Church, Mecklenburg County, than in any other work I ever undertook...."[14]

While carrying forward his constructive work in Chapel Hill and in Durham, Cheshire did not overlook his preparation for the priesthood, although, as he remarked, he did not "feel that impatience to get out of the Diaconate," which he often observed in young clergymen. During his leisure hours he read widely and thoroughly, and was well prepared when the time came for his advancement. At the close of the diocesan convention, held in Winston-Salem, he was ordained priest by Bishop Lyman in St. Paul's Church on May 30, 1880. He was presented for ordination by Rev. John E. C. Smedes, and the sermon for the occasion was preached by Dr. Alfred Watson, later Bishop of East Carolina. Commenting upon the ordination service, the Church Messenger said of Cheshire: "thoroughly active, he will do a work that will tell in the diocese."

During his ministry in Chapel Hill Cheshire received calls from several parishes, all of which offered him a better salary than he was then receiving, but he usually declined them by return mail. In the winter of 1881 the vestry of St. Matthew's, Hillsboro, and the church in Burlington asked him to take charge of their parishes. This prospect appealed to him strongly, since he would live in Hillsboro, his wife's old home, where they had many kinsfolk and friends. Before taking any action, however, he consulted Bishop Lyman, who replied that he preferred Cheshire to remain in Chapel Hill where he was doing a good work. He accepted the Bishop's decision and declined the call to Hillsboro.

About two months later Cheshire received a call from St. Peter's, Charlotte, which he declined immediately. Hearing of this action, Bishop Lyman wrote him that he wished him to accept the charge of St. Peter's. Cheshire replied that he had refused to go to Charlotte because the Bishop had instructed him, only a few months earlier, to remain in Chapel Hill. Bishop Lyman, however, answered that he had directed the vestry of St. Peter's to call him again "and he would see to it" that Cheshire accepted. The call was accordingly renewed, and Cheshire went to Charlotte to interview the vestry. He told them that he accepted the charge because he felt it his "duty to respect the wishes of the Bishop." Cheshire often remarked that during his ministry he never accepted a call to any parish, explaining that the Bishop had directed him to go to Chapel Hill and later to the parish in Charlotte. This was not said in a spirit of criticism of his Bishop but merely as a statement of fact, for he also declared that he "preferred" to have his work given him. Throughout his long life of service he always had the feeling of doing a work assigned to him.

Cheshire quite naturally regretted leaving Chapel Hill, for he had been happy in his work there. He was also reluctant to part with his mission in Durham, which was created in a very real sense by his own labors. Recalling the first three years of his ministry, he declared: "I look upon my life at Chapel Hill as my pupilage, the completion of my training for my life work."[15]