Elmwood's first headmistress, Theodora Philpot, stood out from the crowd in her time. She had seen some of the far corners of the world. She was not afraid to defy convention. She was capable of hard work and, even as a respectable married woman with children, she had plans that went far beyond her own front door. She was an entrepreneur, and her dream was to create a great school.
- 1915: Theodora Philpot establishes Rockcliffe Prep School
- Theodora A. Philpot (born to Scottish parents in 19th-century Burma) establishes the Rockcliffe Preparatory School with four students, male and female, aged four to seven. The old house at Elmwood Farm is its headquarters. The school sets out originally to “prepare” young boys to attend a nearby boys' school at age 11. However, Elmwood also attracts the daughters of Ottawa's elite. Mrs. Philpot is the only teacher at first but soon hires a second to teach French.
- 1916: Junior, Intermediate, Senior Schools established
- Enrolment grows to fourteen, two more teachers join the staff, and the school divides into three sections – under six years of age in the Junior School, from eight to ten in the Intermediate School, and ten to thirteen in the Senior School.
- 1917: Edith Button joins staff
Edith Button, an Englishwoman marooned in Ottawa by wartime lack of transportation, joins the Elmwood staff and remained with the school until 1951.
Mrs. Philpot arranges for the barn on the property to be dragged nearer the old farmhouse to serve as a theatre and assembly hall. It is still there today, much improved, in the shape of the Auditorium.
- 1918: 1st boarder at Elmwood
- Hume Cronyn, who grew up to be a world-famous film actor, boards with the Philpots and becomes Elmwood's unofficial first boarder.
- 1919: Elmwood property purchased
- With enrolment reaching forty-four, Mrs. Philpot needs help to expand. Ethel Fauquier and Lilias Southam, with the assistance of Mrs. Southam's husband, Harry, and her father, the Hon. Thomas Ahearn, purchase the Elmwood property and institution.
- 1920: Clement Buck becomes Head
- Theodora Philpot suffers ill health and returns to England. Her assistant, Mrs. Clement H. (Edith) Buck, becomes the school's second Head. She remains in office for the next 31 years.
- 1922: Incorporation as educational trust
- Elmwood is incorporated as an educational trust under the patronage of Princess Alice, granddaughter of Queen Victoria and wife of Lord Athlone, the Governor General.
- 1923: Rockcliffe Prep School becomes Elmwood
The Rockcliffe Preparatory School changes its name to Elmwood, the name of the original farm, and shifts its vocation from the “preparation” of young boys to the education of young women.
The students establish a school magazine, Samara, to record the events of school life. The publication survives as the school yearbook to this day.
The Honourable Cairine Wilson – first female senator in Canada and the mother of several Elmwood students – donates funds to enlarge and upgrade the barn that has been converted into an Assembly Hall.
- 1925: New building constructed
The doors of the rickety old Keefer farmhouse close, and a new school building is constructed on the site.
The boarding school is established with twenty-four students inhabiting the upper floors of the new building.
The Southam Cup for High Endeavour in the Junior School is donated by Lilias Southam, one-time owner and continuing governor of the school, and her daughters, Janet and Ethel, who are students at the school.
- 1926: School population grows
Elmwood School's student population reaches eighty students, served by a faculty of twelve teachers.
The Wilson Cup for Senior Sports is donated by Cairine Wilson and her daughters.
- 1927: House system instituted
The school population is divided into three Houses – Fry, Nightingale and Keller – as a means to foster team spirit and unity. The Houses are named after prominent women leaders: Elizabeth Fry (who worked for the welfare of prisoners in the 19th century), Florence Nightingale (a pioneer nurse who served in the Crimean War) and Helen Keller (an activist on behalf of the blind and deaf).
The first Elmwood prefects are appointed (nowadays they are elected).
The Fauquier Cup for Junior Sportsmanship is donated by Ethel Fauquier and her daughter, Betty, who was one of the earliest students to attend the school (1916-1926).
- 1939-1945: Elmwood contribution to war effort
- Elmwood graduates serve in the Canadian Armed Forces or go overseas to nurse or drive ambulances. Within the school, a branch of St. John's Ambulance works actively, and the boarding school temporarily houses children evacuated from England. A number of evacuees board at the school as Elmwood's guests.
- 1946: Eastern wing built
- Thomas Ahearn's children (Lilias Southam and Franklin Ahearn) build an eastern wing in memory of their father, who died in 1938. An up-to-date science laboratory commemorates his work as an innovator and inventor in Ottawa.
- 1965: Science Lab constructed
- Fundraising is begun and a new science laboratory constructed.
- 1966: Boarding school closes
- The boarding school closes.
- 1978: IB Diploma Program adopted
- Elmwood becomes the first Canadian independent day school for girls to adopt the International Baccalaureate Diploma Program.
- 1982: Wilson House created
- Wilson House is created and named in honour of Cairine Wilson, Canada's first female senator and long-time Elmwood patron.
- 1981: Development plan, 1st phase undertaken
- Elmwood undertakes the first phase of a $2 million development plan. By 1983, four new classrooms, a laboratory, senior library and computer facility have been built and the school building extensively renovated.
- 1988: Development plan, 2nd phase complete
- The second phase of the development plan, including a double gymnasium, changing rooms, offices, six new classrooms, a music centre and a junior library, is completed.
- 1999: Duke of Edinburgh Program established
The Duke of Edinburgh Award program is established as a co-curricular means to promote individual growth and development through community service and physical activity.
Elmwood introduces a technology program to give its teachers and students access to state-of-the-art instructional, learning and communications tools. By 2004, a revolutionary Laptop Program has given all students from Grades 9 to 12 their own research, creative and communication equipment.
Elmwood transforms the old Headmistress's House into the Advancement Office and a headquarters for alumni and the Parents' and Friends' Association.
- 2001: School Expansion
- With enrolment rising to 500 and with a staff of 70, the school needs to expand. A new Junior School (for Junior Kindergarten to Grade 5) opens on January 8, 2002. The new structure contains seven classrooms, two kindergartens, library, multi-purpose/gym room, computer lab with twenty workstations, science lab, tutoring room and a dining room and kitchen.
- 2004: Old School Renovations
- Work begins to renovate the Old School with, in particular, a new state-of-the-art senior library, as well as art and music rooms and new classrooms.
- 2008: New Head appointed
- Cheryl Boughton is appointed to Head of School effective August 1, 2008. Prior to joining Elmwood, Ms. Boughton served as Deputy Head of Bedford Preparatory School in Bedfordshire, United Kingdom, a single gender independent boarding and day school for 1,100 male students. Previous to Bedford, Ms. Boughton spent eight (8) years working in all-girls' schools in the United Kingdom