Westport Vs. Weston: Which Schools To Choose?

A woman emailed me yesterday. She and her husband grew up in Fairfield County; they now live in Westchester. They want to “come home” to Connecticut — but are torn between Westport and Weston. She says:

I understand the difference between the towns and properties themselves – what I am really interested in (obsessed with?) is the differences between the schools.

My impression is that Weston is more traditional, maybe has fewer course course offerings, but a smaller, more personal experience?

I know both systems are “excellent.” I’m looking, if possible, specifically where there is less pressure (if anywhere) on the kids, and where there is less teaching to the test and true creativity allowed on the parts of the teachers. Any other thoughts are welcome too.

So there you have it, “06880” (and 06883). Click “Comments” to respond. Please address the questions asked — no tangents this time. Please cite specific examples, if possible. And play fair — no ad hominem attacks.

Weston's Hurlbutt Elementary School (left); Westport's Green's Farms El.

Weston’s Hurlbutt Elementary School (left); Westport’s Green’s Farms El.

28 responses to “Westport Vs. Weston: Which Schools To Choose?

  1. Jackie (as I was known back then)

    I wouldn’t be much help. I started kindergarten at Greens Farms School in 1952 when Mrs Leary was the Principal. I remember a Ms Spencer who was my first grade teacher. I really liked her, so if she’s still there, I’ll cast my vote for Greens Farms School as the better of the two!

  2. I grew up in Westport and moved to Weston with my family a few years ago. We were looking for a small town experience after living in large cities. I think you’re right that both school systems are excellent, it’s more a matter of which system fits your children’s personalities better. We knew that smaller would be better with our kids and we’ve been very happy. We’ve now had a child in all three lower schools and been pleased.

    Weston has instituted AIM in the past couple years (Academic Innovation and Measurement) which is teaching towards real world thinking. It’s too extensive to describe here, but the district website would have information. The Superintendent, Dr. Colleen Palmer is very good and I’m sure her office could give you more information.

    Finally, tour the schools that your child might go to. We did in both towns. See what feels right to you.

  3. Richard Lawrence Stein

    I am a product of the Westport schools. I was class of 86. My other siblings were classes 83,89,92, and 98. We all graduated in the top half or better. One of us was even valedictorian. All of us played organized sports. We did pretty well. My cousins went to Weston, but they graduated much more recently. One of them is into sports the other theater… I think you will get a great education, but the extracurricular things like sports and theater are better at Staples… I believe the less esoteric offerings like art, culinary, tv/radio are important different areas that really can excite learning… My 2cents

  4. Sank T. Monious

    You can’t go wrong between the two. I would suggest setting up interviews with administrators and if possible teachers, ask them some open ended questions on the topics that concern you and use that as a springboard to discussion. If you don’t get what you need to make a decision, you might want to consider private schools. I know of no reason why you shouldn’t be able to get exactly what you seek in either Westport or Weston, but it all comes down to compatibility with your values and the degree to which you feel INCLUDED in the education process. Congratulations on your willingness to scratch the surface on this decision. They are YOUR kids and this extra care you are taking will pay off for the rest of their lives and yours.

  5. For every great teacher at Staples (and there are many life-changing ones), there is an appalling one. My kids have had mind-numbing, soul-crushing, nose-thumbing excuses for human beings. You never hear about them in the great publicity machine. They exist.

    • ditto

    • We’ve been in Westport almost 20 years and have three kids. I agree with “Disappointed”. I think Westport schools are a great place if your kid is average or a good student willing to pander to his or her teachers. Being popular with the teachers and having a “reputation” for being a good student is more important than actually being bright or creative. Genuine originality and creativity is only encouraged if it is easily understood. If not, as in our case, the experience can be less than stellar.

      We had one kid with (modest) special needs and we were treated very very poorly in middle school, somewhat better in high school but not what I would consider acceptable. As a parent I felt “bullied” by administration and teachers. I am still fearful of these people (thus I am posting as “Anonymous”.) People may disagree based on their own positive experiences, but I know that what we experienced was not at all uncommon. Draw your own conclusions.

  6. I sent the following note to Dan privately. He responded by asking if I could post it publicly. I did not wish to be a pushy Realtor®, but since Dan asked…. (yes I will be happy to forward those rankings by The Courant to anyone).

    Dear Dan,

    As a Realtor® I get asked this question. But by law I cannot answer it as it is a violation of Federal Law. But I can and do offer an alternative: The school rankings as complied by the Hartford Courant. I have back to 2001. I can email it to the folks who asked if they are interested. By offering a third party compilation I am not “steering” a consumer. If I say a school is great, I could be redirecting them from another potentially valid school. If I say one is bad, obviously that is steering too, and again, a violation of the law.

    But to get a flavor of the schools is even harder, not knowing what the people’s own concerns and core beliefs are.

    I think the bigger question for these people is lifestyle and budget. I can forward you those rankings too so you can understand why there are other more important factors in making that decision.

    Disclaimer: I went all the way through Weston schools (K-12) and have been a resident of Westport for almost 25 years.

    Matt Murray

    Mobile 203.856.3703

  7. Angela McKelvey

    I taught at Weston High School for 25 years. I lived in Westport for 75 years and I and my children went to Wspt schools. Both systems are tops academically. I think the care and concern at Weston for all students is not found in Wspt. If i were you, I’d choose Weston.

  8. I have good friends in both towns who are very happy with the education their kids received. Perhaps the difference is really more comparable to choosing between a small college and a larger one (both of which have excellent reputations)–at least when it comes to thinking about the high school experience.

    I do know that, in terms of certain extracurricular activities at the high school level such as the Staples Players and the Staples varsity soccer program, Westport has exceptionally strong programs that have long, storied histories and active alumni networks (which, I think, is unusual for a high school activity).

  9. Angela, That statement that the Weston School System somehow cares and is more concerned about their students than the Westport School System is a very broad statement and I feel a little uneasy with it. How could one offer any proof for that statement? I’m sure there are thousands and former Westport students and hundreds of teachers who taught in Westport who would strongly disagree. Do you see my point?

  10. Angela, I think the statement that Weston cares and has more concern for their students than Westport makes me a little uncomfortable. First of all it can’t be substantiated, and secondly, I’m sure there are thousands of former students who would disagree with that statement. It also is a little insensitive to those Westport teachers who gave their total commitment to their students

  11. Concerned parent

    I would look at class size. Classes at Staples are reaching 30 in many courses. This has always been the cap but never the norm. It is very typical to be nearing 30 for many sophomore and freshman classes-classes that I feel would really benefit from smaller sizes. Even if they could make more sections, Staples is running out of room. They didn’t seem to plan accordingly when they built the new building and the school seems to be busting at the seams. Lunch waves are really hard on the kids. There are so many kids, it usually takes about 15-20 minutes just to get what they want and pay for their food-and they only have 30 minutes to eat. Of course this is avoided if the kids grab less healthy food or bring their lunch. Staples is a top notch school, but in a few years, they are going to have a serious size problem.

    In terms of the teachers, I do feel that any school has its pros and cons. There will always be some teachers who love what they do but some who are literally just showing up. My children have had pretty decent teachers for the most part-and some of them have been fantastic. But I have heard of other teachers, teachers who seem to only want to make thier students lives difficult. I do feel sometimes that teachers feel that since they are teaching at such a top rated school, students should not complain or question, after all, they must be doing something right if the school is so good.

    I would say go to Weston (as long as they are not busting at the seams)

  12. Fred Cantor nailed it. With the exception of class sizes, Weston and Westport are very similar – high caliber teachers, top notch administrators, and great facilities.

    As someone who went through the Weston school system and now has kids at the Westport schools, however, I agree with Fred Cantor. There is no comparison to the extracurricular programming; Westport is by far the best.

  13. Both towns have top notch schools. The upside of Weston is the land you get, the downside is other than a gas station and a deli you have to go out of town for almost everything. Lots of driving. Virtually nothing kids can walk or bike to. But it’s beautiful and feels more like the country. I think either one is a great choice. I’ve lived in Westport for 40 years and have a daughter at Staples.

  14. The comment on large vs. small seems appropriate. FWIW: the book on Staples is that it’s especially good for gifted students and for students who are challenged, but that kids in the middle might get lost. Whether this is true or not is hard to determine, but it’s a perception that’s been around for a long time.

  15. A westport parent

    We were having this very conversation last night. We live in Westport and our kids go to elementary school in Westport. Our friends live in Weston, and have kids in elementary school there. Both schools are excellent, each year there are great teachers, and not so great, class size fluctuates– my kids have small classes this year– but last year they had 25 kids in their grade. I think the differential is small community– only 1 elementary school in Weston, vs. 5 in Westport. and then everyone knows everyone else through their whole school life– which has its pluses and minuses. We also had friends visiting from Rockville Maryland and California. By comparison, and to give perspective– They don’t have any language programs, music or art at the elementary levels. They were in awe of what is offered at both Weston and Westport schools. So, I think its really a matter of location, -as mentioned above. You can’t go wrong with either school system.

  16. Folks, Isn’t the bottom line that it’s the individual student and their work ethic? There are great students in Bridgeport and Waterbury. There are students who go to Ivy League schools from many school districts. It’s also the home environment which are a factor. Is it video games at night, or reading time?

    • Of course the bottom line is the individual. I think most of us are saying that in one form or another. This woman is asking very specifically for personal reflections on Westport and Weston school systems. You are absolutely right that fantastic students come from all districts, but that doesn’t answer the question asked.

  17. The quality of teachers is only a minor factor. Students that succeed or fail do so despite what their teachers do – same applies at top universites. Also, when you are comparing schools, you used asked yourself, “Excellent compared to what?” I would argue that top schools in Finland, Singapore and Korea should be included in any discussion on the greatness of any Westport “system.”

    • Westport Parent

      I don’t think Finland, Singapore or Korea (North or South? You were not specific) are among the options this family is considering. And I think quality of teachers is a factor especially at the elementary and middle school levels where hopefully a love of learning is instilled that can survive some of the duds one will inevitably encounter in the world of tenured teachers.

  18. I would choose Westport because of a larger population, more accessibility for kids to have independence at an earlier age because you don’t have to drive everywhere, better quality schools. My children attended Weston schools for a few years and now go to private schools. While there are a few stellar teachers, most of the Weston curriculum is geared towards teaching to the test. There are few, if any, long term, analytical problem solving projects and most of the elementary school years are focused on ignoring the children who can actually already read and getting the ones who can’t to catch up. If your child happens to be one of the children in the top 25% and they are well behaved, they will be ignored and left to their own devices with little in the way of challenge or inspiration. My children while no geniuses, were bored because 90% of the teachers are simply interested in meeting the CT State Standards and not interested in really pushing motivated, bright students.

  19. Staples Student

    So, as someone who actually goes to Staples, I can speak a lot to how great some parts of the school are. Most of the teachers are good and there are incredible opportunities in sports, arts, music, etc. – there’s something for everyone. That being said, Staples is incredibly competitive. Those who maybe aren’t the best at something, or can’t find their niche as soon as they enter, sometimes get lost in the crazy pace of Staples.
    Mr. Dodig, a kind person and a good principal, has said that his school goal is to make everyone love Staples; although this is a nice idea, it will probably never happen because Staples has a way of sidelining people who don’t fit right in. It’s not even the traditional outcasts – like, there’s a big community of artists and very few problems with the LGBT students being bullied, and people are encouraged to get good grades, so being a “nerd” isn’t really an insult. Divisions really appear when it gets to junior and senior year and people are applying to college – it’s a really cut-throat environment when it comes to where people want to go.
    So, students do get a good education, and there are very few classes where the average grade is a C, but in return students have to deal with a more competitive social environment. I can’t really speak to how this compares with Weston; I’m just going off my own perspective. Also, I’m not an outcast student so this isn’t a rant against the system. I’m just trying to give an honest statement on student life at Staples.

  20. I am a psychologist living in Westport, who has had many opportunities to observe children in classes in both system. Though my daughter attends school in Westport we have many friends in Weston. I have also lived and worked in many places throughout the country. Here is my perspective: Where ever you go you bring yourself with you, and that is the only constant over which you have a bit of control. Trying to determine which system is best is splitting hairs, most likely. What will make the most difference for your children is your family life. How much screen time do your children have each day, how much time is spent reading, doing puzzles, playing and creating? Does your family make time to just be together and talk? Do you explore the world with open eyes and a sense of wonder?
    If your family is intellectually alive, and a safe, loving place to go when things get rough, then either school system will work for you. If not….
    Many things can change within a school system. A new superintendent or a new principal can result in big changes in the school day, and those changes are unpredictable and not under your control. Therefore, choosing from among two great systems based on subtle differences may backfire. (I once met a family that moved into a specific elementary school district because of a great principal. The parents were outraged when the principal moved on to become superintendent. They felt betrayed). Weston is not so small, really, with a primary school and an intermediate school. Both school systems are in part defined by state mandated testing. And the ridiculous rankings you can read about are really only about those tests, tests that have no value once your child graduates, and tell you very little about how “good” the school is. (Moreover, research shows us that good test scores reflect SES far more than they reflect instruction, teachers, curriculum; our students do well on tests because we are well educated, healthy, and safe)
    About competition: I have met people in both communities that are entirely cut throat and those who are completely laid back. If you do not want your children to treat education as a competitive experience, that too is up to you. And part of what we do as parents is teach our children how to manage those external pressures that do not match our values. So to say that Westport is more intense or competitive makes little sense to me. I have met all sorts of folks here. It is all about the choices you make every day not which of these fine schools and very similar, closely tied communities you choose.
    So I recommend that you make your decision entirely based on your family’s quality of life, commute to work, access to what interests you, etc. Remember that what will help your children thrive, flourish and grow to be the best adults they can be is all available to them regardless of the school system you select. Moreover, as you cannot predict what your children will need later in childhood, there is very little point in anticipating what their unique needs may turn out to be.

    • Not to be verbbose or use jargon: Word! Jill you expressed things very nicely. With the exception of values being testing, Not much is different from when I went through the Weston School system.

  21. A few years ago, the local Realtor® association held a meeting with the Superintendents of the “W” towns and Norwalk (those are the towns of the association). In the Q&A, No Child Left Behind came up, and Landon had been taking heat in the press about it. He volunteered to answer the first question. But the second question the Norwalk Super answered the question about implementing NCLB this way: “Title 9 was three paragraphs when mandated. NCLB is 1,200 pages explaining how to do it.”

    If the only metric are/were those tests, so some amount of time has to be spent to make sure a child passes. Is that a way to learn? No.

    One other thing about the Super in Norwalk: He talked about challenges and issues facing his system. But at one point touched NCLB but he expressed it as “Make Every Child Succeed.” It says the same thing, but what a wonderful way to view it. Unfortunately, he is no longer at Norwalk, but what a wonderful mission statement.

  22. We moved to Westport for the school system and were very disappointed with it. I think have a bit of a biased sample here. The people who send their kids to public school generally like it- or at least they are not unhappy enough with it enough to spend 30k+ per kid, per year on tuition. At our private school there are lots of kids from both Westport and Wilton with similar concerns about the public schools. I suppose the good news is that if you find the public schools to be as inadequate as I do, there are lots of other (although costly) private options. The bad news is that you may be forced to pay a huge tax bill to support a school system that simply can not accommodate you.

  23. Westport schools are excellent. We have had the pleasure of many exceptional teachers in more than a decade here. Many administrators are top notch, and the variety of opportunities is impressive. That said, if you are looking for a nurturing community where your children will develop in an environment where humility and grace are encouraged, this is probably not your best option. Westport is a competitive and sometimes hostile (and painful) place to raise children. Teaching them to apologize when they are wrong is challenging because this is rarely modeled by the parents and guardians in our community. The social environment here unfortunately tends to harden and “toughen up” children beyond what is healthy, in my opinion.