School History
School History

A Brief History of Westover School

Westover was founded by Mary Robbins Hillard, who had been the headmistress of St. Margaret’s School in nearby Waterbury. She convinced the school’s board to support her in establishing a school a few miles away on the south side of the Middlebury Green — “west and over the hills” from St. Margaret’s. Miss Hillard enlisted the help of one of her former students, Theodate Pope Riddle, one of the first American women architects, to design the new School. Westover opened in April 1909 with the boarding students who had been at St. Margaret’s, along with a number of its faculty members, including two who would remain key advisors for Miss Hillard — Lucy Pratt and Helen LaMonte. 

Miss Hillard led Westover for more than two decades, attracting a growing number of young women from leading families from across the country. She introduced a number of traditions to the School to create a sense of community among the students and arranged for a number of prominent speakers, authors, poets, and musicians to visit the School to present lectures and performances.

Upon her death in 1932, Miss Hillard was succeeded by Louise B. Dillingham, a respected educator from Bryn Mawr College. For the next three decades, “Miss D,” as she was known, transformed Westover from what had primarily been a finishing school to a college preparatory institution, attracting a number of gifted teachers who taught for decades at the School. 

Following Miss Dillingham’s retirement in 1964, Westover — like many other independent schools during the time of social upheaval of the late 1960s — faced a period of internal disruptions, a drop in enrollment, financial challenges, and the need to adjust its educational programs if it were to continue to attract and retain students. In 1970, the School began admitting day students and, soon after, began recruiting a new generation of teachers to engage and inspire its students. 

Following the appointment of Joseph L. Molder as headmaster in 1972, Westover over the next decade stabilized and strengthened its educational programs, undertook major fundraising initiatives, and began construction of new facilities, including a new library/science wing. Expanded scholarship programs attracted growing numbers of students and the establishment in the early 1990s of the Women in Science and Engineering (WISE) program introduced one of the first STEM programs in the country. 

Under Molder’s successor — long-time Westover educator Ann S. Pollina, a nationally respected expert on how girls learn — the School was recognized for the growing success of its WISE program, its expanding number of exchange programs with schools from around the world, the introduction of signature programs, the construction of the Fuller Athletic Center, and the renovation of the Louise B. Dillingham facility into the School’s new performing arts center. 

Since celebrating its Centennial in 2009-2010, the School has continued to seek new, imaginative ways to offer educational opportunities to future generations of students. Westover has embarked on its second century of educating students to become confident and connected women leading lives of consequence. 

Heads of School

School Timeline (1909-2002)
1907Mary Robbins Hillard and associate make plans for Westover.  Funds raised through 3,000 shares of stock @ $100.
1909Construction of main building, occupied spring 1909
1910 First class graduates from Westover
1916Virginia House completed (art studios, faculty quarters, Dorcas Room)
1917-1918Westover contributes to Allied Effort, WW I, in spirit and practical means
1919Arrangements made for Carnegie Plan for teachers 5/5% premiums 
1920-25Old Methodist Church bought, used as assembly hall. 60-acre school farm in Woodbury bought. Machine and carpenter shops and garage built
1931Lake Elise property bought to safeguard and improve water supply.  School first accredited.
1932Miss Dillingham arrives to study increase of college preparatory facilities.  Miss Hillard dies, Miss Dillingham appointed headmistress
1933 Hamilton property bought to protect sewage disposal plant.
1935Old Methodist Church and barn reconstructed as biology lab and scenery barn.
1937Old Methodist Church become Mary Hillard Memorial Library
1939-40New Infirmary with 30 beds built and opened
1942Westover incorporated as a non-profit organization under laws of CT.
1941-45Westover students and faculty involved in WW II efforts
1946New opportunities for students to determine their own actions, to go outside the School to learn (UN, NY Times, Metropolitan Opera, plays.  Dorcas and other school groups expand community activities.  Faculty/Student Council initiated.
1947Power House remodeled:  new boilers, change from coal to oil.  First Spring Alumnae Day held and plans made for closer ties between school and alumnae.
1948Mary Hillard Society changed to Westover Alumnae Association.  Work started on an Alumnae Fund to provide scholarships and improve teachers’ salaries.
1949First black student enrolls
1951First endowment fund for scholarship established.  Annual Giving Program started –raised $31,816.  Development Program established.
1953New Over tree planted.
1955First capital campaign.  Five-year campaign raised $760,000.
1957New kitchen installed
1958Upson house purchased for faculty housing.
1959Frisbie property purchased (LaMonte house) for faculty housing.
1959School celebrated 50th anniversary.
1961-63$1,000,000 building and endowment campaign.  Louise Bulkley Dillingham (LBD) activities building constructed.  Main building renovated to provide accommodations for 25 more students.  Enrollment increased from 176 to 202.  Science laboratory provided.  $1.2 mllion endowment.
1964Miss Dillingham retired.  Robert Iglehart succeeded as Head.  Red Hall redecorated.
1965Lee House built.  Two more tennis courts and two paddle tennis courts build.
1966Iglehart resigns.  Miss Hibshman Acting Headmistress.
1967John Alexander appointed Head.
1968Wilkins house on North Street purchased.
1970 Skiff house on North Street purchased.  Trustees decision to remain all girls.  New West tree planted.  Program for Progress campaign announced.  Plan was to raise $5million for endowment and $3million for new library and study center.  Campaign suspended when John Alexander resigned.  Chapel changed to 3 mornings mandatory, 2 evenings voluntary per week.  Coordinate classes with Taft. 
1971John Alexander resigns.  Joseph Molder named acting head.  Trustees vote to limit enrollment to 150 and to admit day students for the first time with a limit of 25 – later increased to 50.  Frugal meals to donate funds to charity during Lent.  Day uniforms abolished.  Earth Day walks.  Enrollment drops by 60 students.
1972Joseph L. Molder appointed Headmaster.
1973Renewal of Program for Progress – goal $5 million for endowment.
1975All-time low for enrollment and endowment.
1977Challenge from T Mandeville – he will give $500,000 provided school raised $1.5 million.
1978Accreditation in peril.  Need for improved science/library facilities.
1982Groundbreaking for Whittaker-Adams Science/Library building.  Gwathmey Seigel design won 5 architectural awards, including the AIA’s highest award.
198475th Anniversary and dedication of Science/Library building.  
1985New Over tree.  Alumnae/Development moved to old library.
1986King Hussein gives graduation address.
1987Exchange program with Ahliyyah School for Girls in Jordan begins.
1988Glowing follow-up accreditation report.
19902nd Century Campaign announced.  Goal of $21 million to build endowment.  Endowment is $10 mllion. Pre-professional program with Manhattan School of Music established.
1992W.I.S.E. (Women in Science and Engineering) Program, joint engineering program with RPI, begins.  $200,000 grant from DeWitt – Wallace Reader’s Digest for minority scholarships in the program.  
1994Full enrollment, highest SSAT scores since 1970.  Annual Fund exceeds $500,000 for first time with 53% participation.
1997Exchange with St. Cyprian’s Girls School in Cape Town.
January 1998Westover receives $6.1 million gift – largest in our history.
1999Joint pre-professional program with Hartford School of Ballet established
June 2000Endowment at $36 million
October 2000Groundbreaking ceremony for new athletic center.  Graham Gund Artchitects.
October 2001Dedication of Fuller Athletic Center
2002Exchange program established with Truro School for Girls in Truro, England
 Ann Pollina named CT Educator of the Year by CT AAUW

Biography About Westover's Architect Theodate Pope Riddle

In addition to designing schools and private homes in Connecticut and New York, Theodate designed and supervised the reconstruction of President Theodore Roosevelt's Birthplace in New York City.

According to writer and critic Brendan Gill, Theodate Pope Riddle was one of the ten most distinguished American women of the 20th century. Her friend, famed psychologist Carl Jung, saw her as an intuitive woman who trusted her instincts, ignored raised eyebrows, and courageously forged ahead despite the restrictions of her day.

  • While Westover School was being constructed on the Middlebury Green a century ago, the School's Founder and First Headmistress, Mary Hillard, visited the building site one moonlit night with her good friend Theodate Pope Riddle, who was the architect for the new School. As they gazed at the sheer size of the project, Mary grew momentarily alarmed at the daunting endeavor she had undertaken. At seeing Mary's unease, Theodate told her good friend, Be still and let your spirit fill the buildings.

Theodate's own spirit still fills the Hill-Stead Museum in Farmington, CT, more than 100 years after she designed it as a country estate for her parents - her first of a number of major architectural achievements.

  • Hill-Stead has been a hub of activity ever since the Pope family first occupied their newly built country estate. Here, from 1901 to 1946, in succession, Alfred and Ada Pope and their daughter Theodate, with her career-diplomat husband John Wallace Riddle, entertained many illustrious individuals - authors, artists, poets, academics, and presidents. 

Art and architecture lovers will want to explore "Dearest of Geniuses", by Sandra L. Katz. The first definitive biography of one of America's first successful female architects.