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In 1854, a company of British officers and two American missionaries was formed in Dehra Dun. Concerned for Protestant education for girls, they solicited the help of a group of English women to help staff and manage what was to become Woodstock School.

1901 saw the elevation of Woodstock into a college. Through affiliation with Allahabad University, young women could obtain a two year First Arts (FA) degree, and in 1910, a BA degree was also offered. In addition to these degrees, a Teacher's Training program recognized by the U.P. education department was established in 1907. Though these programs declined during World War I and eventually dissolved, the architectural and residential growth achieved during this time carried a lasting impact into the next century.

With the 1922 arrival of joint principals Rev. Allen E. Parker and his wife, Irene, Woodstock saw major changes. The school was remade into an interdenominational, coeducational, multiracial and multinational boarding and day school offering a program of study starting with Lower Kindergarten and concluding with either Senior Cambridge credentials or the equivalent of an American high school diploma.

Because of the war, the early thirties brought a rapid increase of students to the school, primarily students of British parents and also students from China. The late forties proved to be a time of high staff turnover and low finances, but Woodstock's educational and co-curricular programming continued to advance.

The 1950s were significant years for the school on many levels. A high point of the decade was Woodstock's centennial celebration. In 1959, Woodstock was the third High School outside North America and the first school in Asia to receive US accreditation through the Middle States Association of Colleges and Secondary Schools.

During the 1960s, Indian Music classes were introduced, as were cross-cultural courses in social studies, literature, art, and religion. Indian universities became more accepting of the Woodstock Diploma. The Woodstock "Package Program" came into being with eight students from the U.S. originally taking part. Hiking, always a part of Woodstock's recreation, was encouraged in the Elementary School by the formation of a Hiking Club.

From the late 1960s through the 1970s, Woodstock consciously shifted its conception from that of a missionary school to a school consisting of an international student body, staff, and curriculum, with a strong Indian cultural component. The Cambridge course, which had been dropped earlier from the curriculum, was replaced by the General Certificate of Education ( London ). During the late seventies there was also a marked influx of students for whom English was not a first language, and an English as a Second Language (ESL) program was established in 1978 for Grades 1 through 11.

In 1990, the Association of Indian Universities recognized the Woodstock Diploma as being equivalent to the Indian school leaving examination, thus allowing graduates to enter Indian universities with greater ease.

Throughout the 1980s and 1990s, there existed a notable emphasis on environmental and community development and service on the part of the students. After the earthquake in October 1991, activity groups rendered assistance to the Budhkedar region (U.P.). This and other ongoing service projects still receive assistance from staff and students.

In recent years, Woodstock has placed a priority on its academic programming with renovations to classrooms and laboratories, the introduction of contemporary classes such as Environmental Sciences, an increase in the number of US Colleges Advanced Placement examinations offered to and taken by seniors, and the 2003 requirement of all seniors to sit for the Cambridge University IGCSE examinations at Grade 10. During 1999, Woodstock completed its application for continuing accreditation with MSA under the 'Accreditation For Growth' protocol, for the K-12 program.