Cheshire's first personal contact with the work of the church outside of North Carolina was with the University of the South at Sewanee, Tennessee. Feeling that the churchmen of his Diocese displayed an unwarrantable lack of interest in the welfare of the University of the South, he resolved to bring to their attention the needs and opportunities of the institution. In 1885 he made an appeal for support of the school in the columns of the _Church Messenger_. He wrote personal letters to prominent churchmen, and made addresses on behalf of the University in as many parishes as he could conveniently reach. His voluntary efforts met with some success. Perceiving Cheshire's active interest in the school, Dr. Jarvis Buxton, clerical trustee for the University from the Diocese of North Carolina, resigned this position at the convention of 1885. Dr. Buxton then nominated Cheshire to succeed him, and the convention unanimously confirmed his nomination. From 1887 until he was elected bishop he attended every meeting of the trustees. During this period Cheshire formed many lasting friendships with the trustees and professors he met at Sewanee. These associations gave him a better understanding of the church's work outside of his Diocese. The diocesan convention further recognized Cheshire's ability by electing him one of the clerical deputies to the Triennial General Convention of 1886. He was re-elected a deputy to the succeeding conventions of 1889 and 1892. As far as the journals reveal, he did not take an active part in any of these meetings. It was characteristic of him to have little to say in a body of which he was a new member until he had become thoroughly acquainted with its personnel and procedure. At the General Convention of 1889 he was made a member of the Missionary Council and was re-elected to the Council in 1892. Attendance upon these conventions further broadened his knowledge of the work of the national church and brought him into contact with many of its prominent figures.