Bishop Cheshire gradually placed more responsibility on Bishop Penick as he became better acquainted with the work of the Diocese. A characteristic act of Bishop Cheshire's, and one which claimed the admiration of his people, was the turning over of the work at Chapel Hill to Bishop Penick's supervision. The Chapel of the Cross at Chapel Hill had been the Bishop's first parish and he had always retained for it a deep affection. Therefore, it was a personal sacrifice for him to relinquish it to another. He felt that, due to the peculiar nature of the work at Chapel Hill, it should be under the guidance of a younger man.

As Bishop Cheshire grew older he began to plan how best he could provide for his wife and daughter when they would no longer be able to live at Ravenscroft, the Bishop's house. He decided to build a small apartment house in Raleigh, which would produce an income as well as provide a home for them. When the house was completed he advertised the apartments for rent only to families with children. He thought the frequent practice of denying apartments to persons with children was most unfair and, therefore, determined to make his house an exception. This was typical of the Bishop, who loved children and large families.

In building his apartment house Bishop Cheshire had to borrow a part of the cost of its construction. Speaking of this to Bishop Penick, he remarked he hoped to live four years longer since by that time his loan would be retired. Recalling this observation Bishop Penick decided to raise a sum of money from among the people of the Diocese to relieve the Bishop of this care. The money was raised by the time the diocesan convention met in the spring of 1924 at Winston-Salem. It was a fitting time and place for the presentation of the gift, since it was at Winston-Salem thirty years before that Bishop Cheshire presided over his first convention. The gift, which amounted to $4,273, was presented to the Bishop from the people of the Diocese by Dr. Richard H. Lewis, who said in part: "My dear Bishop: By your strong and vigorous intellect, your wide and accurate learning, your public spirit, your unspotted character, and a personality of unaffected friendship, you have come to be—in the words of another—'one of the best known and best loved men in our State.'" Referring to this generous expression of affection, Bishop Cheshire remarked that he could never "cease to feel grateful to him whose generosity conceived the idea, and to the many kind friends who responded to his suggestion, and transmuted his thoughts into act."

At this convention the Bishop delivered an address in which he briefly reviewed the high points in the thirty years of his episcopate. He declared he wished to repeat a major point he had made in his first episcopal address in 1894, namely, the importance of realizing the "common bond of union in the Diocese by becoming interested in common Diocesan work." During the past three decades Bishop Cheshire had accomplished more than any of his predecessors in breaking down parochialism by arousing in his people a lively interest in diocesan enterprises. The Bishop concluded the review of his work by saying that the past thirty years had been happy ones, "years in which I have received much love, consideration, and kindness from all our people, clerical and lay."

The unusual and praiseworthy feature of the general esteem in which Bishop Cheshire was held in North Carolina was the demonstration of that esteem during his lifetime. The churchmen did not wait until his death to eulogize him and to erect memorials in his honor. On many occasions and in many different ways he was made to realize the high place which he held in the hearts of his people.

After completing thirty-five years as bishop of the Diocese of North Carolina, a longer period than any of his predecessors, Bishop Cheshire felt that he must give up the greater part of his work. He therefore informed the convention of 1929 that he was turning over to Bishop Penick the general administration of the entire Diocese. He thought that the ever-increasing and more complicated work of the church required a younger and more vigorous man, one, as he expressed it, "more adaptable and more in sympathy with changing conditions and methods." Of Bishop Penick he said: "We have one whom we all believe to be eminently fitted to carry on the Diocese with success and with the confidence, sympathy and affection of all." Bishop Cheshire did not intend, however, to relinquish all of his duties. He retained for himself the episcopal oversight of about one-third of the parishes and missions, the keeping of the diocesan register, and the requisite business before the Standing Committee. The parishes which he reserved for his own visitations were all located within a convenient distance from Raleigh.

Bishop Cheshire was not present at the convention of 1929 because of the serious illness of Mrs. Cheshire. Bishop Penick read his address. It was the first diocesan convention that he had failed to attend since 1876 when he had been present as a lay delegate. Mrs. Cheshire died before the convention adjourned. Accordingly, resolutions of sympathy for the Bishop were adopted, and a committee was appointed to represent the convention at Mrs. Cheshire's funeral. The death of his wife was a great loss to the Bishop; their life of thirty years together had been happy and congenial. Mrs. Cheshire had been a generous mother to his small children, and a helpful and devoted wife.

Although his strength was gradually failing, Bishop Cheshire displayed during the next three years a remarkable activity. For one of his years he preserved an unusually tolerant attitude towards the many religious, social, and political changes of the day. When, on his eightieth birthday, he was asked what he thought of the youth of today, the Bishop replied: "The world is a much better place than it was when I was a young man.... Young people today have more personal religion than they did then."[59] While he disapproved of much that was done by the youth of today, he thought that his parents must have had much of the same sort of disapproval of his own generation. "When people talk," said the Bishop, "of the degeneration of the morals and manners of the present, and praise the good old times and old time religion, as being so much superior to the present, they do not know what the old times were, and in my opinion, they are often speaking nonsense. That is my very serious opinion."[60] In making this observation he did not mean to depreciate the religion of his forefathers, for no one had a greater respect and veneration for the past.

During the last year of his life Bishop Cheshire filled almost all of his regular visitations in the eastern part of the Diocese. In addition, he spent ten days, in the month of July, visiting the country churches in the counties of Rowan, Mecklenburg, Davie, and Iredell. In the course of these visitations he called on forty families in the several parishes and missions. Such activity in midsummer would have taxed the strength of a far younger man, but it did not appear to trouble the Bishop. At the time, he wrote his son that although the heat was very severe, he noticed it no more than if he had been doing nothing. In June of 1932 the Bishop went to Hartford, Connecticut, to assist in the consecration of a new chapel at his alma mater, Trinity College. He enjoyed the trip thoroughly, renewing some of his old friendships and making new ones.

By the fall of 1932 Bishop Cheshire's health was greatly impaired, but he continued his visitations through December 11. On that day he performed his last service. He confirmed a class of fifteen persons in the Church of the Good Shepherd, Raleigh, but was not able to preach the sermon. A few days later he went to Charlotte for treatment by a specialist. Shortly after entering the hospital, however, he became gradually worse. On December 27, at six-thirty in the evening, the Diocese of North Carolina lost its beloved Bishop.