Oak Grove School was the product of coming together of three of the greatest gifts of Nineteenth century - Indian Railways, Hill Station and Public School Culture -all blending harmoniously in this institution. The first Railway hill school was started in 1870s by SP&D Railway later known as North Western Railway at a Bungalow called FAIRLAWN close to the land where Oak Grove is presently situated. It was part of the 'Rajah's Palace' which belonged to the Royal family of Nepal. The ruins of the Palace are still present and part of the estate has been developed for residential purpose.

Oak Grove school was started in 1888 by East India Railway Company with an endowment fund of Rs 2 lac on the recommendations of the School Committee. In the 19th century Companies and Industrial concerns were mainly driven by profit motive and rarely invested in areas of social concern like Educational institutions, which was mainly left to Religious and Philanthropic Institutions. It was therefore quite creditable on the part of EIR to start an institution like Oak Grove, way back in the 1880's.

The proposal soon took concrete shape and the school started functioning from 1st of June 1888. The Fairlawn school was merged to Oak Grove in 1894 as it could not survive the birth pangs like shortage of staff and accommodation.

The first School building, the present Boys school was designed by Mr. R. Roskell Bayne , the Company's Chief Architect and built under the supervision of Mr. W. Drysdale the Company's Engineer. Earliest recorded history of the school mentions the arrival of Matron and Sergant Mrs. and Mr. Green on 9th May 1988 as the first official of the school followed by Head teachers Mrs. and Mr. A. C. Chapman on 19th May, who steered the school through its initial teething problems and set it on the path of stable growth over the period of 24 years, which they spent here.