About

Mission and History

Westover School empowers young women to lead lives of consequence.

Our Core Values

List of 4 items.

  • Strength of Character

    We foster citizens of the world who are compassionate, brave, and resilient advocates for themselves and others.

  • Women's Empowerment

    We empower young women to take action as confident leaders by discovering their individual voices through exploration, reflection, and global awareness.

  • Passion for Learning

    We champion enthusiasm and engagement as we cultivate innate curiosity into an enduring love of learning.

  • Community

    We nurture an inclusive, diverse, and welcoming community rooted in our traditions. Through our shared experience, we forge meaningful, supportive, and enduring relationships.

A Brief History of Westover School

  • Our Founder, Mary Robbins Hillard

    Westover was founded by Mary Robbins Hillard, who had been the headmistress of St. Margaret’s School in nearby Waterbury.
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  • Westover Traditions and a Growing Community

    Miss Hillard led Westover for more than two decades, attracting a growing number of young women from leading families from across the country.
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  • Louise B. Dillingham

    Upon her death in 1932, Miss Hillard was succeeded by Louise B. Dillingham, a respected educator from Bryn Mawr College.
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  • Stabilizing and Strengthening Educational Programs

    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.
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  • A Growing Success, Expansion of Programs

    Under Molder’s successor — long-time Westover educator Ann S. Pollina, a nationally respected expert on how girls learn.
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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.

Be Boldly You

1237 Whittemore Road
Middlebury, CT 06762
1 (203) 758-2423

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Westover School admits students of any race, color, religious affiliation, sexual orientation, national and ethnic origin, or disability to all the rights, privileges, programs, and activities generally accorded or made available to students at the School. As a gender-diverse girls school, Westover welcomes applicants and students who are assigned female at birth and/or identify as girls. The School does not discriminate on the basis of race, color, religious affiliation, sexual orientation, national and ethnic origin, disability, or any other status protected by applicable law in the administration of its educational policies, admissions and financial aid policies, and athletic or other school-administered programs.