Earlier this month, I gave a tour of Staples High School to the 50th reunion class of 1964.
Dozens of Social Security recipients — many of whom looked like they could still fit into their varsity letter jackets or cheerleading skirts — wandered wide-eyed through a 3-story building filled with Wi-Fi, whiteboards, and enough flat-screen TVs to make Best Buy go gaga.
The address was familiar: 70 North Avenue. But in the half-century since they graduated, the school underwent several major changes. Besides athletic fields, the auditorium and the JFK “Ask not…” plaque — a gift of that class to the school — there’s little they recognized.
Staples is an extreme example. But nearly every Westport school has been renovated — or at least reconfigured — since it was built.
In honor of the 1st week of school, here’s a look back at how our 8 schools got where they are.

The original Staples High School on Riverside Avenue.
Staples High School. The first classes were held in the National Hall building — the red brick structure across the Post Road bridge from downtown — because Horace Staples’ Riverside Avenue school was not yet ready. That structure — located approximately where the Saugatuck Elementary School auditorium is today — opened on October 31, 1884.
In 1937, a 2nd building opened just north of the 1st. It’s now the central unit of Saugatuck El (minus the gym and cafeteria wing). That 2nd addition was added in 1948.

The “modern” Staples — now Saugatuck Elementary School.
Ten years later, Staples moved to its present North Avenue site. The sparkling new school included 7 buildings, connected only by open-air walkways. Three more buildings were constructed 5 years later. It was great in the early fall and late spring, not so smart the rest of the year.

The 1st version of the North Avenue campus: 7 separate buildings.
Later, in a 3-year project ending beginning in 1978, the 9 separate buildings were connected. That version of Staples lasted until 2005, when the $74 million current school — built while the old one was being demolished — opened for business.
Bedford Middle School. For 42 years starting in 1884, 7th through 9th graders attended the same small original Staples on Riverside Avenue. In 1926 they moved across Doubleday Field to a new “Bedford Junior High” (now Kings Highway Elementary School). In 1958, BJHS took over the recently vacated Staples on Riverside Avenue. It was renamed Bedford Middle School in 1983, when Staples became a 4-year high school. Then, in the 1990s, it too moved all the way across town. A sparkling new Bedford rose just north of Staples, on the site of a former Nike missile base. The only connection it has to the 1st school is a bust of its original namesake, Edward T. Bedford.
Coleytown Middle School. First opened in 1965 as Westport’s 3rd junior high school, Coleytown looked like the most futuristic school imaginable. Debates raged for years as to whether the circular design worked or not. (Architect Joseph Salerno’s building was, however, selected for a national exhibition on school design.) It became a middle school in 1983, and more than a decade later underwent a substantial renovation.

Coleytown Junior High (Photo/Fred Cantor)
Coleytown Elementary School. Despite one renovation, this school has not changed much since it opened in the early 1950s. It’s got its original bones — and it’s always been an elementary school.
Green’s Farms Elementary School. It looks like it’s been there on South Morningside forever. Though it has, the current building is much larger than the original. And it was on hiatus for a while in the 1980s and ’90s, when our school population dipped substantially. In those years, the building served as home to the Westport Arts Center.
Kings Highway Elementary School. Until 1958, this building was the site of Bedford Junior High. That year, it became an elementary school. If you look closely, you can still see the “Bedford” name over the front door.
Long Lots Elementary School. Opened in 1955 as Westport’s 2nd junior high, it has undergone numerous renovations and changes. It’s morphed from a junior high to a K-8 school, and now it’s just an elementary school. The northernmost wing burned to the ground in 1974, in a fire set by an 8th grader.

Long Lots, when it was a junior high.
Saugatuck Elementary School. Riverside Avenue — home of the old Staples High and Bedford Junior/Middle School — is the 2nd location for Saugatuck El. For nearly a century it sat on Bridge Street, where the Saugatuck elderly housing complex is now. Its original name was the Bridge Street School.
In memoriam:
Bedford Elementary School. A handsome building on Myrtle Avenue near the center of town, it was repurposed 30 or so years ago as Town Hall.
Burr Farms Elementary School (approximately 1958-83). Perhaps the cheapest, most hastily built school in the history of education. Made of steel (perhaps tin), it was nonetheless a great place (and, not coincidentally, my alma mater). Today it is the site of homes and athletic fields, near the start of Burr School Road off Long Lots.

Burr Farms Elementary School (computer image by Steve Katz)
Hillspoint (approximately 1960-85). Some brainiac had the idea of putting the gym in the center of a circular building. Noise problems, anyone? Today it’s a childcare center on Hillspoint Road.
(Got any good — or bad — memories of your Westport school building? Click “Comments” below. Please include your real name — and graduation date.)