A personal look inside Staples High School—from a Class of 1981 graduate who recently returned for her reunion
If you’re considering a move to Westport, Connecticut, one of the questions you’re likely to have is: What is Staples High School really like?
The answer is more interesting than a school ranking or a list of statistics.
Staples is a large, comprehensive public high school with a remarkably broad range of academic, athletic, artistic and extracurricular opportunities. It is also a school with a long history in Westport—and one that has changed considerably since I walked its halls as a student.
I was reminded of that recently when I returned to Staples for my Class of 1981 reunion.
Our reunion included a tour of the school, and walking through the building again after 45 years was a wonderful opportunity to see what has changed, what has stayed the same, and what today’s Staples students have available to them.
For families already living in Westport—or considering a move here—I thought I’d share some of what I learned and some of the questions I hear most often.
Where is Staples High School?
Staples High School is located at 70 North Avenue in Westport and serves students in grades 9 through 12.
The school is part of the Westport Public Schools system. Current school materials describe Staples as a comprehensive high school with approximately 1,850 students, offering a broad curriculum as well as extensive opportunities outside the classroom.
For families moving into Westport, permanent residency in the town is the primary requirement for enrollment. Owning property or paying taxes in Westport, by itself, does not establish school residency.
What is Staples High School known for?
Academics are certainly an important part of the Staples experience, but one thing that stood out to me during my recent visit was how much more there is going on beyond the traditional classroom.
Staples currently offers more than 150 extracurricular opportunities, including clubs, athletics, art, music and theater. The school describes these activities as an important part of helping students discover their interests, develop teamwork and creative problem-solving skills, and build relationships within the school community.
That breadth is one of the things I think prospective families should understand about Staples.
There isn’t just one definition of a successful Staples student.
A student may be deeply focused on academics. Another may discover a passion for theater, music, journalism, radio, athletics, technology or community involvement. And many students combine several of those interests.
That variety was very evident during our tour.
Staples Players: A Westport Tradition That Continues
One of the things I was particularly excited to see again was the performing arts program.
Staples Players has a long-standing reputation for excellence, and the current Staples website describes the organization as being famous for producing some of the best student theater in the country. It is a year-round program with opportunities not only for actors, but also for students interested in technical theater and instrumental music.
The theater department offers courses including Theater I: Acting Fundamentals, Theater II: Advanced Acting, Theater III: Acting Technique and Theater III: Directing. Students also have opportunities to participate in major productions, Studio Theater productions and the One Act Play Festival.
During our reunion tour, I was able to see behind the scenes, including areas of the theater that are currently undergoing renovation.
During our reunion tour, I was able to see behind the scenes, including areas of the theater that are currently undergoing renovation.
That was particularly fun for me because I remember Staples from a very different era.
And there’s more than one performance space.
⬅️ Click image for the quick tour!
Staples also has a Black Box Theater, which provides a more intimate setting for student productions and other performances. The school’s theater information describes Studio Theater productions and student-organized performances taking place in the Black Box and other venues.
For a community with such a strong artistic identity, having these kinds of opportunities within a public high school is pretty remarkable.
More Than Theater: Music, Media and Radio
The arts at Staples extend well beyond the stage.
Current Staples materials highlight programs in art, music, theater, media and technology education, among other areas.
And during our tour, I came across something that I don’t remember from my own high-school days: an ON AIR/radio space.
Staples actually has a long history of student broadcasting. The school’s current handbook identifies WWPT-FM 90.3, a student radio station, as one of the school’s facilities.
For students interested in communications, journalism, broadcasting or media production, this is the kind of hands-on experience that can turn an interest into a real skill.
And Staples has other ways for students to tell stories and engage with the community, including Inklings, the school’s student news organization. One of our classmates brought an Inklings issue from 1981, which we were comparing to the May 2026 issue!
Athletics Are a Major Part of the Staples Experience
Staples also has extensive athletic facilities and programs.
During our tour, I photographed the pool, field house, track, and field, which give a good visual sense of the scale of the school’s athletic offerings.
The school maintains a dedicated athletics department, with sports registration, coaching resources, student-athlete information and NCAA guidance for students considering collegiate athletics.
For families with student-athletes, that combination of competitive athletics and college-planning resources can be an important consideration.
What About Academics at Staples?
Staples describes its curriculum as “broad and deep,” with the goal of helping students develop programs of study around their individual strengths, interests, challenges and post-high-school goals.
The school offers Advanced Placement opportunities as well as a wide range of courses across traditional academic departments and more specialized areas.
The current program extends beyond the standard core subjects to include areas such as:
- Art
- Music
- Theater
- Media
- Technology education
- Culinary arts
- Career and vocational offerings
- Online learning opportunities
The current new-student guide also highlights more than 100 co-curricular clubs, while the newer extracurricular resource lists more than 150 offerings across clubs, athletics, music and theater.
For parents moving to Westport, that distinction matters.
The question isn’t simply, “Is Staples a good school?”
A better question is:
Does Staples offer opportunities that fit my particular child?
With its size and breadth, there is a good chance that students can find an academic, artistic, athletic or extracurricular niche that genuinely interests them.
What Happens After Staples?
For many families, college preparation is naturally an important consideration.
Staples has a dedicated school counseling department and resources addressing college applications, financial aid, scholarships, military pathways and athletics in the college admissions process. The principal told us that the majority of students continue onto college, with approximately 93-96% attending four-year schools.
But one of the things I also appreciated hearing during our reunion was the emphasis on helping students prepare for their own next chapter, rather than assuming there is only one definition of success.
That philosophy is consistent with Staples’ stated mission of helping students pursue individual strengths, interests and post-high-school goals.
A Global Perspective
One of the most interesting parts of our reunion was hearing from the principal about the experiences available to students today—including travel opportunities to destinations around the world.
That was a striking reminder of how much the definition of a high-school education has expanded.
Students can learn about another culture in a classroom.
But actually experiencing that culture, traveling with classmates and teachers, and seeing another part of the world firsthand can create an entirely different kind of learning.
This was one of the details I found particularly meaningful because it reflects something I noticed throughout the tour: Staples seems to be trying to prepare students not just for the next test or the next school, but for a much larger world.
How Did Staples Get Through COVID?
Our principal also talked with us about the school’s experience during COVID.
For those of us who graduated decades ago, it was fascinating to hear what it took to keep a large public high school community functioning through such an extraordinary disruption.
The experience was a reminder that a school isn’t simply a building or a curriculum.
It’s a community of students, teachers, administrators and families—and maintaining that community during a crisis required an enormous amount of adaptation.
“No Hate Here” and Creating a Welcoming School Community
Another thing I noticed as we walked through the building was the messaging throughout the school about belonging and inclusion.
I photographed bulletin boards and signs, including “No Hate Here”, a Pride board and the “Respect for Life” mantra permanently etched into the school’s seal.
These aren’t academic statistics, but they are part of what a school communicates about its culture.
The Westport Public Schools describes the community as valuing a town that is welcoming to people of all kinds and encourages students to engage with the broader community.
As someone returning to Staples after 45 years, I found these visual reminders particularly interesting.
The building may have changed.
The technology has certainly changed.
The opportunities have expanded enormously.
But the idea that a school is also a community remains just as important.
What Surprised Me Most About Returning to Staples?
Probably the sheer breadth of opportunity.
When I attended Staples, I obviously experienced it through the lens of a teenager in the late 1970s and early 1980s.
Returning as an adult—and now as a Realtor who spends so much time talking with families about what it is like to live in Westport—gave me an entirely different perspective.
I wasn’t looking at Staples wondering which class I would take next.
I was looking at it through the eyes of a parent considering a move.
I noticed the athletic facilities.
The performing arts.
The theater spaces.
The radio studio.
The bulletin boards.
The classrooms.
The opportunities for travel.
The range of extracurricular activities.
And perhaps most of all, I noticed how much there is for a student to discover.
That may be one of the best things about a comprehensive high school of this size.
Staples High School: Frequently Asked Questions
Is Staples High School a public school?
Yes. Staples High School is the public high school serving Westport, Connecticut, for grades 9–12.
Where is Staples High School located?
Staples is located at 70 North Avenue, Westport, CT 06880.
How many students attend Staples High School?
Current Staples enrollment information describes approximately 1,850 students in grades 9–12.
Does Staples High School offer AP classes?
Yes. Staples offers Advanced Placement courses, with information maintained through its school counseling department.
What extracurricular activities are available at Staples?
Staples currently lists more than 150 extracurricular offerings, including clubs, athletics, music and theater.
Does Staples have a theater program?
Yes. Staples has a dedicated theater department and the renowned Staples Players, along with Studio Theater and One Act opportunities.
Does Staples have a Black Box Theater?
Yes. The school uses its Black Box Theater for Studio Theater and other student performances.
Does Staples have a radio station?
Yes. Staples’ handbook identifies WWPT-FM 90.3 as the school’s radio station.
Does Staples offer athletics?
Yes. Staples has a dedicated athletics department and a broad interscholastic athletics program, with resources for student-athletes and families.
What middle schools feed into Staples?
Westport’s public-school system includes Bedford Middle School and Coleytown Middle School, which serve Westport students before they move on to Staples.
Do you have to live in Westport to attend Staples?
For ordinary public-school enrollment, yes. Westport residency is the primary requirement for enrollment. Simply owning property or paying taxes in Westport does not establish residency for school purposes.
A Realtor’s Perspective: Why Schools Matter When You’re Moving to Westport
When people move to Westport, they are rarely buying a house in isolation.
They’re choosing a community.
They’re thinking about commute times, beaches, parks, restaurants, cultural opportunities, neighbors, recreation—and, for families with children, schools.
That’s why I think it is important for prospective buyers to look beyond a school ranking.
Visit the town.
Explore the neighborhoods.
Understand the school system.
Ask questions.
And think about whether the community—and the opportunities available within it—fit your family’s particular needs.
For me, returning to Staples after 45 years made that perspective especially personal.
I first knew Staples as a student.
Today, I know it as a Realtor, a Westport-area resident and someone who helps people make decisions about where they want to live.
And now I have had the unusual opportunity to see it from both sides.
A Special Connection to a Neighborhood Home
My recent return to Staples also happened at an interesting time professionally.
I’m preparing to bring a wonderful home to the market—a home located just down the road from Staples.
That gave my reunion visit an additional perspective.
As I walked through Staples again, I found myself thinking about what today’s families are looking for when they choose Westport—not simply in a home, but in the lifestyle and community surrounding it.
That’s ultimately what makes Westport such a special place to call home.
If you’re considering buying or selling in Westport, Fairfield or the surrounding coastal communities, I’m always happy to share what I know about the neighborhoods, schools, lifestyle and real estate market.
— Linda Raymond, Realtor | William Raveis Real Estate | 203-912-4440
Fairfield and Westport CT Real Estate Guide 