The turbulent history of Staples High in Westport

Another school year has begun. At Staples High, there’s a familiar buzz of activity. Dozens of classes, ranging from advanced environmental studies and Mandarin to advanced cooking and radio production, are held daily. Athletes practice fall sports; The Players’ Theater Group is rehearsing the fall production of ‘Guys and Dolls’.

Everything looks so neat, so tidy, so traditional – exactly what anyone would expect from a powerful and successful school. But Staples’ path to 2022 was anything but predestined. There have been many twists and turns to arrive at its place as one of the best public schools in the country.

Newcomers may not realize the long history of the local high school. Westporters who have lived here for a long time – even (especially?) current students – may not know the story either. There’s no way to capture Staples’ 138 years in 800 words. But here are some highlights.

The school was founded in 1884 by Horace Staples. (There’s the answer to “why is your school named after an office supply store?”) He was 83, having been born when Thomas Jefferson was president. The richest man in town – he owned stores, ships, an ax factory and a bank – was tired of watching boys and girls ride wagons to schools in Norwalk and Bridgeport.

In 1884, after 16 years of repeated rejection by the city, he finally began building a school on land he owned near his Riverside Avenue home. (The original building was demolished in 1967; we know it today as the site of Saugatuck Elementary School.) The dedication ceremony was grand; the whole city shut down for the day and the governor gave a speech.

In the second year of operation, the manager was Wilbur Cross. He was only 22 years old; the position of director was in fact “main teacher” (out of a faculty of six). After a “hard cider” negotiating session with Horace Staples, Cross agreed to a $700 salary. Principal left the following year, for a long and distinguished career as a professor at Yale University. In his 70s, he was elected Governor of Connecticut (and had a boardwalk named after him).
“Staples’ High School” (with an apostrophe) included students in grades seven through 12. The first promotion, in 1887, consisted of six girls. All the boys dropped out earlier, to work in factories or on farms.

Horace Staples died in 1897, at the remarkable age of 95. Until then, his birthday (January 30) had been celebrated as Founders’ Day. He visited the school, attended lessons and was the guest of honor at an assembly. The tradition continued a few years after his death.

In 1903 the town of Westport took over the school. Until then, students paid tuition fees. Now Staples was an entirely public high school.

In 1907, the first fire drill was held. An athletics club – reserved for boys – is organized. Two years later, the State Board of Education declared Staples one of the best high schools in Connecticut.

The first yearbook was published in 1912. Five years later a new group – the Parent Teacher Association – began. In 1918, partly because of the insistence of this group—with America fighting in World War I—the German language was dropped from the curriculum.

A proposal to add Spanish to the foreign language department (which included only French and Latin) was rejected. It was believed that students hardly needed to learn to speak Spanish.

1923 was a banner year in Staples history. The first newspaper, called Inklings, is published and a “meal counter” is opened. Previously, students who lived nearby went home for lunch. Not everyone could do that, of course; they came from as far away as Weston and Wilton. These students ate lunch in their classrooms or headed to nearby downtown Westport or the village of Saugatuck.

In 1925, Gladys Mansir was hired as an English teacher. She stayed there for 40 years. His pragmatic approach to grammar, literature and writing has impacted generations of students. Four years later, Walter Stevenson began teaching mathematics. He had a similar influence.

The following year, a new building—part of what is now Saugatuck El—opened next to the wooden Staples High (which was still in use), to serve the growing school population. Bedford Junior High School opened for students in grades seven through ninth, across from Staples. (That building is now Kings Highway Elementary.) Staples lacked an auditorium and gymnasium, however, so high school students traveled to BJHS to play basketball and play plays.

In 1931 Inklings, the student newspaper, started. A “college preparatory course” began; these students were separated from those in business or general courses. Meanwhile, the Depression affected Staples. Enrollment surged as parents were unable to afford tuition at private schools attended by many wealthier students.

World War II and the post-war baby boom helped make Staples a more modern school – much closer to what it is today. Next week’s “Woog’s World” explores those years.

Dan Woog is a writer from Westport. His new “Calendar Close-up” column appears every Friday and dives into one of Westport’s upcoming community events. He can be contacted at [email protected] His personal blog is

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