In 1853, Rev. Henry Winter Syle entered a school called Bartlett 's School. The school then moved from New York to Hartford, Connecticut. He went to school with some of the well-known Deaf people in the education of the Deaf, like John B. Hotchkiss and George Wing at the American School for the Deaf.

He entered Trinity College in 1863 but he left the school because he was very sick. He witnessed the Inauguration of the National College for the Deaf and Dumb in 1864. He wanted to go to the National College for the Deaf and Dumb but the president of the college, Dr. Edward Miner Gallaudet encouraged him not to enter the college but instead enter St. John's College in Cambridge, England.

Rev. Henry Winter Syle left St. John's College because of his illness. He then entered Yale College and took an examination of the 4 years worth of education and passed with a Bachelor of Arts in 1869 and Master of Arts in 1872. He was the first Deaf man to get a degree from a hearing college.

He took a job teaching at the New York Institution for the Deaf in 1869. He met his future wife, Margaret Flannery, of Brooklyn, New York, a graduate of the Class of 1870 of the New York Institution for the Deaf. They married in 1872.

He was also a librarian of the New York Institution for the Deaf and compiled the original and valuable Register of Pupils, whose pupils were admitted to the Institution form 1854-1875. He opened a free night school for the Deaf in New York. After he quit teaching, he went on to work at the U. S. Mint in Philadelphia, Pennsylvania.

He became an active religious leader, as a lay reader. He was involved with Dr. Thomas Gallaudet's missions for the Deaf. He also started studying for Holy Orders while working at the U.S. Mint. He was ordained in 1876 by a Bishop of Philadelphia as a deacon of the Protestant Episcopal Church.

Rev. Henry Winter Syle and his wife, Margaret, better known as Maggie, had 6 children. Two of their children died very young. All of his children were hearing.

On October 14, 1884, Rev. Henry Winter Syle was ordained to priesthood by Bishop William Bacon Stevens at St. Stephen's Church, becoming the first Deaf priest in the United States. He helped to improve the Church Mission to the Deaf in Pennsylvania, Delaware, and New Jersey. He also founded the All Soul's Church in Philadelphia.

He was not only active in the Church but also in the Deaf community. He wrote in the American Annals of the Deaf and the Deaf Mutes' Journal. He was involved in the Clerc Literary Association. He helped established the Aged and Infirm Deaf-Mutes in Philadelphia.