Ever since he left college Cheshire had been conscious of a growing desire to become a candidate for Holy Orders. Not long after his marriage he spoke to his wife of this aspiration, and told her he had now decided to present himself to the Bishop. He had not come to this decision earlier because he was determined not to go into the ministry until he had made a success of what he was doing at that time. He would not enter the ministry as a failure from another field of work. By the middle of 1876 he decided that he was making a respectable living for his wife and himself. He thereupon told his father of his decision and sent Bishop Atkinson his application. Shortly afterwards the Bishop accepted him as a candidate for Holy Orders, and Cheshire began preparing himself for his new work.

It was Cheshire's original plan to attend the General Theological Seminary in New York for a year or two, but Bishop Atkinson and his father dissuaded him from this course because they objected to the Dean of the Seminary and because they felt that its ritualistic influences were too strong. Bishop Atkinson thought that, since Cheshire had had a good classical education, had pursued intellectual interests, and had been reared in a clergyman's family, he could quite adequately do his preparatory work at home. Cheshire accepted the Bishop's advice, and at once began a well laid-out course of reading. He had already read a good many ecclesiastical works, since he had been contemplating this step for some time.

At the end of 1877 he gave up his connection with the Pamlico Insurance and Banking Company, and soon afterwards concluded his legal affairs. In September, 1877, he went to Raleigh to stand his examinations for the diaconate before Rev. Dr. Matthias M. Marshall and Rev. John E. C. Smedes. Having passed his examinations acceptably, Cheshire was ordained deacon by Bishop Atkinson on April 21, 1878, in Calvary Church, Tarboro. His father presented him for ordination. The following Sunday he assisted his father in the morning service and preached his first sermon. Thus he was launched upon a new career in which he was to rise to heights far beyond his modest dreams.

When Dr. Kemp Plummer Battle, President of the University of North Carolina, heard that Cheshire was studying for the ministry, he asked Bishop Atkinson to send him to Chapel Hill. Dr. Battle was a native of Edgecombe County and had known Cheshire and his family for many years. Since the revival of the University in 1875, Rev. Robert B. Sutton, of Pittsboro, had from time to time held services in the Chapel of the Cross. The Chapel Hill churchmen, however, felt that the parish needed a regular and resident minister. The Bishop complied with Dr. Battle's request and informed Cheshire that he was to serve his diaconate in Chapel Hill under the direction of Dr. Sutton. This was a disappointment to Cheshire, for he had hoped he would be able to remain in Edgecombe County and strengthen the church's position there. The Bishop also directed him to hold a regular appointment in the rapidly growing town of Durham, where as yet there was not even an established mission. This was a difficult assignment for a young deacon just beginning his ministry. In Chapel Hill he had to revive an old parish which had fallen somewhat into decay during the hard years of the reconstruction period, while in Durham he had to build from the ground up, commencing with only a handful of church people.

Cheshire came to Chapel Hill in May, and on the nineteenth of that month held his first service in the Chapel of the Cross. President Battle invited him to make his home at his house until he could find a suitable place. Cheshire accepted this generous offer and spent several weeks with the Battles. In consequence of a long illness, contracted soon after his arrival, he did not hold another service in Chapel Hill until the last Sunday in June. The next Sunday he was able to keep his first appointment in Durham, but following this service, he had a serious relapse and was unable to continue his work until early fall.

For a few weeks that fall Cheshire boarded at the hotel, while his wife visited her family in Hillsboro. This gave him an excellent opportunity to come into close contact with the students, many of whom took their meals at the hotel. In this way he came to know a number of students who were not members of his church. Throughout his rectorship in Chapel Hill he made it a point to know all the students who were in any way connected with the Episcopal Church. In a comparatively short time he was on friendly terms with most of the small student body.

Cheshire frankly confessed that in the first exercise of his ministerial duties among the students he felt "great embarrassment" and even some "timidity." He explained: "I had not been accustomed to speak much of my own religious feelings; and I was at a loss how to make a proper approach to the subject of another person's religious duties and convictions."[8] He visited the boys in their rooms when he thought they liked it, but never sought to force himself upon them. Cheshire later declared he did not remember ever approaching a student on the subject of religion without receiving a serious and courteous hearing. Many students seemed to appreciate the interest he took in their religious life. Cheshire himself was only a few years older than many of the undergraduates and, therefore, could understand their point of view and enter sympathetically into their problems. The effectiveness of his first year's work in Chapel Hill was demonstrated when Bishop Lyman made his visitation to the Chapel of the Cross in May, 1879. Cheshire presented to the Bishop for confirmation nine students and two girls of the village. In later years he remarked that this was "one of the most interesting and satisfactory classes I ever presented."

When he first began preaching, Cheshire took great pains in the preparation of his sermons, writing them out in full. He freely admitted he had "no special gifts or talents as a speaker." In discussing the problem of preaching with Cheshire just after his ordination, Bishop Atkinson said he would give him the same advice which Bishop Johns, of Virginia, used to give his young deacons: "Choose a pretty long text, so that if they persecute you in one city, you may flee to another." Cheshire began, in time, to memorize his sermons and then to attempt to preach extemporaneously, but he always felt that his written sermons were better. Concerning the reception of his sermons in Chapel Hill, he stated: "My Chapel Hill congregation seemed to me most considerate and appreciative of my attempts at preaching, even the students of the University, so far as I could judge."[9]

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]