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

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.