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Gill St. Bernard's is the result of the merger of two Somerset Hills schools — St. Bernard's School for boys in Gladstone and The Gill School for girls in Bernardsville.
St. Bernard's School was founded in 1900 by the Rev. Thomas A. Conover. It was his vision to establish a school for farm and village boys where they could be educated at the same time they learned a trade. The first group of boys came to St. Bernard's in September of 1900. They were charged $100 a year for their room and board.
In the early days, academic classes alternated with work in the carpentry shop, the print shop or on the farm. Daily attendance at religious services was required. In 1912 the highest award for a student was established, and has been given ever since. The Julian T. Brown Cup was given to the school by Brown's mother in memory of her son who died shortly after leaving St. Bernard's. The actual silver cup was inherited from an ancestor who owned the plantation next to Thomas Jefferson's Monticello. Tradition stated that the author of the Declaration of Independence had drunk from the cup. Recipients of the award have their names engraved on the cup, which resides in a place of honor at the school.
In 1945, Rev. Robert L. Clayton, Jr. was named Headmaster. He brought a broader vision of operation to the school. It was under his leadership that St. Bernard's moved to a concept of academic excellence. The emphasis now was on scholarship, with an aim being the integration of the education program with the needs of industry. The emphasis of the work program on physical well-being, discipline and personal industry still played a large role in the philosophy of the school, while a college preparatory program started to gain momentum.
The Gill School was established by Miss Elizabeth Gill in 1934 as the Wychwood School. Her educational philosophy was based on the value of the individual and she sought, through small classes and direct teacher-student relationships, to establish a "rich school experience" for the pupils. The physical development of the individual was encouraged, with at least two hours each day spent out-of-doors. The first graduating class consisted of three students.
Three years later the school moved to Mendham and changed its name to Miss Gill's School in the Mendham Hills. The physical facility was only rented, however, and in 1940 Miss Gill's School purchased Stronghold, the former Dryden estate on Bernardsville mountain. The building was dedicated by the spiritual advisor of the Gill School - Rev. Thomas A. Conover, who was also rector of St. Bernard's School.
In the early 1940's a coeducational middle school was added to the all-girls boarding high school. In 1956, boarding was discontinued.
The 1960's and 1970's were turbulent times for the country and for education in general. Coeducation was becoming more fashionable, and in 1972 St. Bernard's School combined with Miss Gill's School to become Gill St. Bernard's. At this time the religious affiliation of the St. Bernard's School was discontinued. The new school had younger students on the old Gill campus in Bernardsville and older students at the St. Bernard's campus in Gladstone.
The two divisions consolidated in 1996 in Gladstone. Today there are three divisions - a Lower, a Middle and an Upper School - located on 79 acres which span the Somerset-Morris County line between the Boro of Peapack-Gladstone and Chester Township. The school today consists of seventeen buildings which include  Upper, Middle and Lower School facilities, two athletic centers, a theater and four administrative buildings. There are also a field lodge, five playing fields, a track, seven tennis courts and an outdoor swimming pool.