In 1861 a school was established and taught by John Miller in a bark Skillion attached to a hut occupied by Adam Windsor. It was situated at the northeast corner of Bong Bong and Boolwey Sts. In 1859 a survey was completed with Rev. James Hassall telling JN Oxley that a reserve for a church, parsonage, schoolhouse and a glebe of 43 acres and 3 roads had to be made. In August 1861 a visit to the southern district by Bishop Barker saw him lay the foundation stone for the building to intended as a church and school in Bowral. JN Oxley planned the structure and local residents erected it with money being subscribed by them. In late 1863 the school was operational with the first teacher being John Elkin who in 1867 resigned and became an Anglican Minister.

The school was known as Wingecarribee and controlled by the denominational board. Enrolment was 111 in 1864 with many pupils belonging to the men who worked on the construction of the railway line. The building was overcrowded as it only sat 80 pupils. In 1865 68 pupils were on the roll.

Rev. J Hassall initiated a move to convert the denominational school to a public school after the resignation of J Elkin. Mr Hassall wanted J Warren of Cobbitty as the teacher but he would not accept unless the school was conveyed to the Council of Education. The Council agreed to the proposal, the Denominational Board was paid £100 and Warren was appointed teacher in 1868. A teacher's residence was built in October 1869 at a cost of £349.

A tender was accepted for additions to the school to accommodate 65 pupils in 1882 with a brick room for infants being built in 1885. In 1889 the school was divided into two departments and on the 11th November 1889 a new building for boys came into use. Bowral became a superior public school with three departments in 1892. In March 1894 additions costing over £843 were opened with a two-storey brick building being completed in February 1898.

Bowral became a district school in 1906 and in 1932 the cottage next to the school was bought and converted into an assembly hall for the school.

The District School became the Intermediate High School with the first group of students to reach Leaving Certificate standard sitting the examination in 1915. Construction of the high school began in 1929 with the foundation stone being laid on the 5th June 1929 by Hon. DH Drummond, MLA, and Minister for Education. In February 1930 140 students beginning their studies occupied the new building. The headmaster was H Cowie BA until his death in 1935.

Bowral has been an educational centre for many years. Mrs. Howard Reed erected "Woodbine" in Woodbine Street, Bowral in 1876 and opened a school early the following year. In 1882 Mrs. West and Miss Sullivan established a boarding school in Burradoo. The Sydney Church of England Girls Grammar School rented and opened a branch at "Woodbine". In 1929 the Council of the school acquired a site in Moss Vale, which was intended for a Masonic School. The house on the land was reconstructed and in 1930 the school moved into the building. In 1921 the Methodist Church bought 52 acres of land on Kangaloon Rd with the site being dedicated in the November of 1921. Susannah Annesley who married Samuel Wesley and had two famous preachers John and Charles Wesley had a the Annesley School named after her which was opened on the 3rd of February 1924 with Miss Agnes Wheen MA, Dip.Ed. as Headmistress.

A free kindergarten school was organised by Mrs Stranger Leathes opened in October 1901. In order to begin work two rooms had to be rented but in April 1902 the school shifted to a new room that was built by the Presbyterian Church. The school eventually closed but in 1906 a new kindergarten opened in Merrigang Street by a retiree from the Department of Education Mrs Russell, which also ended up closing. In 1948 a temporary kindergarten was opened in St Judes Parish Hall with a permanent kindergarten called Bowral Memorial Kindergarten being established by a committee in February 1949. This is now known as Gumnut Preschool. On the 4th of July 1956 the old bowls clubhouse was bought and a school was opened with 26 students.