The history of Woodstock school begins in 1854. In that year, four ladies from the 'London Society for Promoting Female Education in the East' landed in Calcutta and began the long journey up to Mussoorie. They had come in response to an appeal from a committee in Mussoorie consisting of three army officers, the Chaplain of Mussoorie and two American missionaries. Their aim was to start a Protestant Christian School of a quality equivalent to that of Waverley convent, which had opened in 1854.
The school opened in Cainville Estate. One year later, in 1855, it moved to the other end of Mussoorie, to the Woodstock Estate, where it has continued without a break ever since. The house named Woodstock had been constructed in 1842 by Col. Reilly. In 1867 after Col. Reilly's death, the school purchased the estate from his widow.
The estate adjacent to Woodstock, known as Midlands, was owned by Mr. George Taylor of the East India Company, after whom Taylor's flat is named. In the first decade of the 20th century, Woodstock School was expanding and a teacher's training college was added to the school. To accommodate the college, Woodstock purchased the Midlands Estate and expanded the old to house the college. The college building closed in 1935 and the building became the senior girls' hostel, Midlands, a function which continues to this day. Woodstock School at the end of 1991 had a strength of 462 pupils - all boarders - from 30 different nationalities and an international set of teachers. The school is still predominantly American in character; its alumni are to be found holding responsible posts in the U.S.A., India and many other countries. All those who have studied at Woodstock have fond memories of the Woodstock grounds which extend down to the streams on each of Midlands, and which contain a wonderful variety of trees, including oak, chestnut and rhododendron.