Be Honest!

“06880” gets plenty of requests for advice.  Usually we just blow them off respond politely.

But a recent email demands serious reflection, and in-depth responses.

Not from “06880,” though.  From you — our loyal, passionate, and uber-opinionated readers.

A former Westporter who now lives elsewhere wrote:

I need some real info — as real as you can get.  My husband and I want to move east within the next year.  I’m seriously considering Fairfield, Norwalk Stamford… but my heart is Westport.

However, that may be through a very filmy and possibly faulty lens of my childhood there.

I’m working with a nice realtor there.  I’ve asked her, and she assures me there are still wonderful, real and down-to-earth people in Westport.  That’s important to me.

For a year, I’ve read blogs and articles about living in Westport.  A lot of it isn’t favorable.  The terrible things I’ve read really bother me.  Westport’s reputation can be horrible online when it comes to rich, overindulged, shallow people.  Is there a balance there like everywhere else, I’m hoping?

An iconic view of Westport.

My mind wanders there, my heart wants to take me back there to live, and I know so many streets with my eyes closed, the curve of the shoreline as you drive to Compo.  That never leaves you, and I’ve wanted to go back for some time.  I listen to my intuition.

But I don’t want to be fooled by being too sentimental either.  Is Westport as bad as some say it is?  That’s so hard to believe.

I would love to know your true thoughts.  Be real with me.  The good, bad and the ugly.   What’s still magical?  What’s really changed since the 1960s and early ’70s when we were kids there?  Are there still wonderful people there?

I’ve read that young people don’t stay and businesses are moving out.  Is this so?

Another symbol of Westport.

I know this is a long question.  But I’ve had a whole year to read some not so great stuff about Westport not being vibrant anymore, and a rich people’s playground, blah, blah blog! and Wesporters of today.

We will be there this fall, and maybe stay at the Longshore Inn.  I’ve made a reservation for a couple of nights so we can just see.

There’s your challenge, “06880”-ers.  An ex-Westporter wants to know about Westport today — the good, the bad and the ugly.  Just click on the “Comments” tab, and write the “real info.”

And at the end of your response, please answer 1 question:  Should she move back, or not?

80 responses to “Be Honest!

  1. I would say go to Fairfield. Much more to do, nicer people, more diverse, (compared to Westport at least), and if you have kids, they actually have before and after school care right there, at the schools. I too moved back after being away for a few years…..and was was working here the entire time before I physically moved back…… NOT the place we remember. Sorry. I know it can be hard to hear, but trust me, if my family were not so entrenched here already, we’d move to Fairfield, too!

  2. I returned to Westport, my hometown, about eight years ago after 26 in Atlanta. Sadly, much of what you describe as the “new Westport” is true. I don’t need to beat that dead horse, but it is what it is. Conspicuous consumption comes to mind when looking at the town today. The good side, and it’s still a very good side, is that so much of the old town is still very present. Many old friends of my family and my Staples days are still here. The artistic and cultural life here is as strong as ever and we have those unique jewels called Compo and Longshore. My wife and I now live in Black Rock ($$$$) and use Fairfield for most things. Fairfield has done a fantastic job of upgrading their town and it’s the happening place for restaurants and socializing (especially on the young family side). If your memories of Westport way back then are still strong, then you’ll find them again if you come home….

  3. Richard Lawrence Stein

    Former 06880er… Westport has changed very dramatically… Good or bad is arguable… Beauty is in the eye of the beholder…as a person who has been here since 1973 I personally think being here is great… I also think the adage of what you put into it is what you get out of it… If you can afford a home of your liking then go for it… If you can not go to Fairfield… Many great things there just once more removed from the NYC commute…. The simple answer to your questions is unequivocally YES!!! Just remember like college or high school… Some classes you liked, some kids you liked, some people or places you avoided some you were drawn too. But like your memory of the past things change some stays the same…

  4. What a great idea to reach out to the community for more information before making your move. I wish I had done that. I didn’t grow up in Westport so I knew only what I’d heard about it before I moved here nearly 10 years ago. I would likely be considered part of the wave of transplants that’s killing the “old” Westport. Except I came her for a dose of the “old” Westport too.
    I moved here for the quaint New England town, the gorgeous beaches, and the artsy community. Ten years later I can echo what the other commenters have said, Fairfield is the new Westport. Downtown Westport is on it’s agonal breath, the beach and waterfront are barely used (zoning reasons maybe?) to their full effect….I’m not talking about a Starbuck’s waterfront, but how bout a little clam shack or a fruit stand near Compo, or more waterfront restaurants downtown?
    Sadly there is an increasing lack of contentment among the residents. The cars are HUGE, the pace can be frantic and the opportunity for relationships scant.
    Having said that..I still live here. I have a wonderful group of down to earth friends who drive hybrids and eat locally and participate in the local art scene. I’m part of a growing movement to improve the school food and green the town. Green CPR for Westport if you ask me!
    My advice? Come here. We need you. Just come eyes wide open and call me. I’ll have you and your kids over for tea and to play with my chickens!
    Good luck!

  5. Dick Lowenstein

    “When you finally go back to your old hometown, you find it wasn’t the old home you missed but your childhood”

    —- Sam Ewing

  6. Interesting article.
    After living in White Plains for 25 years, I still miss the beach and beauty of Westport, but I think my kids had much more diversity and better values growing up in a mixed community.
    I think enviornment and peers are a factor in shaping young people, but if the parents have their values and heads in the right place, I have to believe, the kidss will follow.

  7. From the perspective of some one who has lived in Westport since 1978, I would offer the opinion that for better or worse the town is nothing like it was 30 years ago. Three decades ago Westport had a bohemian live-and-let live ambiance. Now, the town is full of meddlesome busybodies, who according to Mr. Joseloff, are busy suing each other because of imagined or real slights and transgressions. It is as if the creative people have been replaced with trip and fall lawyers and individuals who have little or no experience living in a fairly small town. On the other hand, most of us have choices about where we live, and we have chosen Westport. The beach is still nice, when the dogs are not soiling it. The schools sytem is still adequate, althought I did send my younger two children to private schools. The taxes are high, and rising with each year. The movie theaters are gone, but the town government is an endless source of amusement. The Westport Playhouse is a gem. One of the few institutions in Westport to have improved over the last 32 years. If you need to be close to a train, Westport is not a bad choice, but if you do not, I would choose Weston or Wilton.

    • Richard Lawrence Stein

      Funny thing Jeff the taxes in both of those towns are higher and there is a whole lot less to do and commuting is lot more difficult

      • Perhaps, but the taxes in Westport are rising. The schools in Westport are overrated compared to the schools in Weston and Wilton, and in those two towns your neighbor is much less likely to be a trip and fall lawyer

        • Wait what is the difference between Weston High, Staples High and Wilton High…and how would you know the difference?

          • Agreed. How can you claim that Staples is overrated? As a student I’ve experienced first hand just how great the school is. Why would you send your kids to private school, when we have the number one rated public school in Connecticut? When you live in one of the richest counties in America, you’re going to find some snobby people. You’ll see that in any town in Fairfield County. Not to mention that both Wilton and Weston have no downtown, and absolutely nothing to do. Why do you think Weston kids takeover Westport every weekend? And whats wrong with having a lawyer for a neighbor?

          • Staples High School is no better than average when compared to its reference group. I realize that challenging the myth of Staples is akin to pointing out that the emperor has no clothes, but some of us have a broader set of experiences than those who have seen nothing but the Westport public schools which are expensive, but average.

          • Rude and Smooth

            Why do you equate “rich” with “snobbery.” I find the wannabes are far more snooty than the wealthy. Assumption denied.

          • You need some help with your math. The all in cost per student at Staple is closer to $20,000. You need some help with civics as well. I chose to spend whatever I spent on my children. I had no choice when it came to your expenses. See the difference?

        • Richard Lawrence Stein

          Jeff this is where we will always agree to disagree… Both my sisters teach in other school systems… And I have seen been around many other school kids… There is just no comparison… But that is your point of view

          • jeff…I’m not even backing up Staples, but to call it expensive is ridiculous considering you sent 2 of your kids to private school (there are few private schools in CT that I know of that is less than 10k a year).

            I’m not really sure what you are comparing Staples too…the Wilton and Weston public high schools? I’d say they’re about equal although I can’t truly defend it…and no, those dumb CAPT scores do not tell you how good a school actually high schoolers try on those.

    • @Jeff:

      I began visiting Westport in 1966 and after several summer rentals became a full-time resident in 1980. I now live in Weston, but consider myself a Westporter. While I certainly deplore and abhor what has happened to Westport it is still most probably the best major city suburb in America. As for Weston and/or Wilton there is simply no there there in either of those towns.

      As for taxes compare the mill rates. As for town government I think that the current one has done and continues to do a more than the average. And the schools are as good as public schools in this country get (same for Weston and Wilton). One day parents around these 3 towns will understand that in loco parentis does not mean that the schools and teachers are the only ones responsible for the students.

      So Jeffxs why don’t you choose Weston or Wilton? Or do you need to be closer to a train?

      • Moving requires transaction costs, and Westport is closer to my office. Mill rates do not tell the whole story. I have this debate with a former first selectmen and tax assessor. If the value of the house is biased upward in the valuation process, the mill rate is understated. I travel extensively. Everyone thinks that his or her suburb is the best. Whether you are in Denver, or Chicago, or Atlanta, or LA, or San Diego, you will find suburbs full of people who are sure that their burb is just the best in the whole US. As to the quality of Westport’ government, it is pathetic. The rank incompetence would not be that much of an issue if the town fathers/mothers were not such meddlesome fools.

  8. All of the qualities found in people who live in the Wash-NY-Boston corridor that the rest of the country dislikes can be found here: superiority complexes, poor listening skills, narcissism, aggressive driving, a self-involved intensity that colors every action. Returning to Westport after an absence of several weeks, while doing errands the first couple of days back I always am struck by the grim disposition of so many people I encounter around town doing errands. It always reminds me of the time a couple of years ago when I took my son, Jack to hear Ishmael Beah, the author of the book, A Long Way Gone, speak in New York. At the end of the interview Tom Brokaw asked him what surprised him about America, now that he had been here 7 or so years. He said, “Here, everyone has so much and yet everyone is so unhappy.” Having said all this, I nonetheless know from my own experience that there are plenty of genuinely nice and sincere people in this town quietly going about the task of trying to raise decent, well-adjusted, optimistic kids and who also contribute to the community’s well-being in many ways that go unadvertised. There are countless ways in this community to live a meaningful and satisfying life. It’s your mindset that counts. I completely agree with Dick Lowenstein’s comment, too!

  9. As Thomas Wolfe put it, “You Can’t Go Home Again.”

  10. If you don’t need good schools, then East Norwalk south of 136 has some very enjoyable neighborhoods. I lived on Saugatuck Shores twice (4 + 12), and it is still wonderful, but you have to like to be close to salt water – very close, like in your driveway. You may notice that no one has suggested Greenwich, New Canaan, or Darien. I’d add Wilton to your list, and seriously consider Fairfield, as suggested above.
    If you’re moving back to CT for the same reasons we did, then it won’t matter which town you move to – the same bunch of over-achieving, over-involved, smart, funny, and caring people are still all over Fairfield County. Things have changed with the times, but I still call Westport my hometown, with pride.
    PS: We moved to PA for work reasons two years ago, and we miss Westport a lot.

  11. Westport has changed there is no going back. I have lived here for 20 years and there are a lot more snobby residents now than I remember there being 20 years ago. One private road wants a “no right turn” sign at the top of a hill so that there will be less traffic going by their road. By traffic I am talking about going from maybe 3 cars at a time passing to 5 cars. Moving to westport? I would say rent first and see how you like the “new Westport” if you do, then buy and if you don’t well there is npthing perminate so you can move to a place you like better. Good Luck

  12. Anon - Staying in Westport

    We are in Westport for 16 years or so. We were seriously contemplating a move to FFLD this past summer. Our house was on the market and we had a buyer. Surprisingly, the prices in Fairfield were too inflated and we couldn’t find the value we were looking for there. Timing is everything. Prices in FFLD have “normalized” and there are some real good bargains there now. We stayed, as it just doesn’t make sense for us to move now that the kids are starting school in a couple of weeks.

    My advice? If I were you, I’d move to Fairfield. I love Westport but I think the schools are way way over rated (sorry Dan, nothing to do with you) and if you have a special needs kid, OMG, don’t come here! They are just plain mean to special needs kids (and parents) here! And Fairfield has much of what Westport has with slightly less of the “over the top” culture. Not too much less, mind you, but just slightly less.

  13. Let me just preface this by saying that there is good and bad about every town on the map. There are truly wonderful things about Westport that tell me I should urge you to move back. But there are also not such good things that often have me contemplating leaving. I grew up here in Westport, too, and moved back about ten years ago when my children were young. I have mixed feelings about Westport. I didn’t really plan to move back here, it just kind of happened. We looked at real estate in neighboring towns and we happened to find “the one” in Westport. It was a comfort, too, to still have my parents here. They have since moved away, so I no longer have the old homestead to return to for family gatherings which was part of what made our return here so welcoming. Westport is not what it once was. Many of its gems still exist: Compo Beach, Longshore, the stunning drive along the Gold Coast, the picturesque Nyala Farms well, sledding at Winslow park, a sandwich at Oscars, the friendly staff at the Sherwood Diner, the colorful flags on the bridge, the fireworks on the Fourth of July, the Levitt Pavilion. I could go on, but if you grew up here you know what I mean. But yes, much has changed. I am constantly astonished by the entitlement so many people demonstrate here. The blowing off of stop signs, the running of red lights, pulling around from behind a stopped school bus as the kids cross the street to board. And those are just the drivers. I could take up much room in this little box just writing about them. I am not a millionaire, but here they are a-plenty. And they flaunt it. It’s hard keeping up with the Joneses. It is reported that a newly crowned sixteen year old boy received a red Ferrari for his birthday and drives it to Staples daily. Porsche convertibles and Hummers will run you down to get that parking space right in front of Starbucks, or, they’ll just invent a space and leave the car idling while they just run in to get their tall iced coffee in a grande cup with extra ice, three pumps hazelnut, two pumps classic, an inch of non-fat milk, with a dome lid and a venti straw. If you have a child with special needs, be prepared to fight the school system for support. If your child excels in just about everything, which seems to be the goal of many parents here, then he or she will probably be just fine, but will undoubtedly be inventing parking spaces, too, the very day he or she gets his or her license.

    However…. please know that while I complain about these things, I also believe, as I said earlier, that this is likely the case in many communities here in Fairfield County. Life in general ain’t what it used to be. Westport has so much to offer and if you take advantage of all of that and you appreciate it then you will enjoy being here again. I DO enjoy living here again, but it is a different experience than what I remember as a child. Of course, as a child, I knew nothing about the Joneses or red Ferraris. Starbucks didn’t exist. I just enjoyed riding my bike to the beach and helping my mom choose the best ears of corn at Rippes. I agree with Jennifer, above, who said that we need you! We need people who can help Westport maintain some of its old charm. Jennifer, can I come for tea, too?

  14. I have not lived here long, but I find Westport to be an amazing town in many ways. I’ve never seen such thorough planning or sincere efforts toward diversity in a small, wealthy town. People do put their money where their mouth is, and want input from all of the residents.

    The facilities and experiences available are excellent, but it is difficult to meet people here. There is a definite snobbishness in general, and it is accepted that minorities will do all of the work for everyone; perhaps not quite so much personal work now that the recession has made folks give up some of their luxury help

    From day one the most disturbing thing is the DRIVERS in Westport. The rudest I have EVER encountered, bearing down on you in their shiny giants and honking if you are not twenty miles over the speed limit or if you dare tap your break or hesitate for one second at a light. Obnoxious to the point of flipping out if you don’t quickly turn right where it says “No Right Turn” Awful.

    The schools are great but the Do Good Cliques of parents are doing bad things and making it uncomfortable to get involved in their fascist world overthrow, on either side.

    Unfortunately, it is true that most Westporters look very unhappy. Maybe it’s the loss of nannies and weekly beauty sessions, pared down time at the club or being forced to eat at four-star restaurants since the economy collapsed.

    I personally think that the men are stressed by money and their status, and the women are starving and having to decide whether their allowance goes to fix their wrinkles or buy new designer duds. Everyone looks good from the back, and then you see the weight of the world on their tense faces with mouths pulled down at the sides.

    Teens can’t wait to get out of here and maybe that’s what’s upsetting the adults. All they do is for these pampered pets, and what is the thanks they get? Another formidable dose of angst: What in the world will the spouse and I talk about when the kids aren’t here to distract us? The answer is more tiny dogs.

    Most people here have tiny dogs. You see huge men walking tiny dogs on Soundview. Without dogs or smartphones, people might feel they have to acknowledge eachother. This is a modern-era phenomenon, but it’s already hard to make friends here and this does not help. Granted, I go to bed too early to partake of the classes and sport groups, etc., so it’s partly my problem I haven’t acclimated too well. But it’s definitely difficult for an outsider.

    Since you are not an outsider, you will probably do fine. You will strike up conversations with other “natives” and be allowed into the bubble once again. I’m sure of that. You just may LOVE it and I will sincerely be happy for you if you do. Best of luck!

  15. FAIRFIELD!!!!!!!!

  16. I still have plenty of people questioning my sanity for moving from California to the New York area aka New Canaan and then Westport. My response: “There are pluses and minuses no matter where you live”

    Sure there are the crazy drivers, self involved people who can make you nuts, weather that is either wonderful or horrible, crime, shopping, great or not so great schools, but isn’t this why you become part of a community?

    I happen to really like living in a town where there is so much happening and people who care, even if I don’t always agree with everything they say.

  17. The issue comes down to whether you have school-aged children. If so, then prepared to meet many of the “new” Westporters whom you have read about. If not, then welcome back to a town that you can fashion into your own.

    I, too, suggest that you rent for a year and come to your own conclusion. Good luck, and hope to see you soon.

  18. Dennis Jackson

    As a former Westporter since 1949 and now a Wiltonian since 1981, my observation is that Westport is all the things you describe. There seems to be a large core of down to earth people, and it is still a great town, a vibrant, active, creative hotbed.

    As ever, its reputation precedes it, making it an address to have. So there is also a substantial contingent of nouveau riche, many (but not all) of whom participated in big money or dot com deals and got their piece, which made them oodles of money, but unfortunately not always class. Their aggressiveness plays out in their choices of (huge, expensive) cars, “me first” driving habits, and other forms of pushiness, self-indulgence, and show-offiness. In the old days, the money was generally more modest, and might have been earned by being creative on Madison Ave rather than being tough on Wall St. Of course, if one has a chance to know these people as individuals, they often turn out to be very nice.

    Westport can also get crowded. Traffic can be heavy, so patience is a virtue required for the maintenance of sanity. Compo gets filled up, parking is hard to find downtown, etc. Our solution was to move to the woods of north Wilton where we have 2 acre zoning, superb schools, and still use wells and septic systems, and then visit Westport. But its heavily corporate and Republican and has no access to LI Sound. Weston might be a nice compromise.

  19. Wow. I opened this up curious to see what good things my fellow residents had to say about Westport. Instead, they urged a move to Fairfield (where the property taxes are even higher than they are in Westport, by the way).

    So, let me take a dissenting point of view. Westport has surely grown and certainly changed over time. Every town in Fairfield County has. Sure, there is a higher percentage of affluent residents in Westport now. So what? Are you all implying that people who earn more money are bad neighbors because of it? I reject that notion.

    Come back to Westport and see how great all of the micro-communities are. They are significant and filled with caring people. See how wonderful the soccer communities are, the tennis teams, the people playing golf and paddle tennis, the churches and synagogues, the volunteer organizations. The town is vibrant. The people care and are kind to each other. They associate, often, in these micro-communities of like minded people who come together over similar interests. Take them together and they form a passionate and nice group.

    We love Westport.

    And as for the bad driving — it is everywhere. My wife and I blame the cell phones and the multiplicity of other electronic devices. It is no worse in Westport than anywhere else.

    Come on back. You’ll enjoy it even if it is not the Westport of your youth.

  20. Wow. As the Jeremy d. Said I thought I would see all the wonderful things people said. We’re been here nearly 20 years, have two kids that have gone thru/currently in the school system. Any town is what you make it. There are dozens of groups that do great things for this town and would welcome you. No one mentioned the library or the Levitt. Hopefully a new direction is coming for downtown. We have great friends that we’ve met here and are children can’t imagine living anywhere else. One problem, everyone loves tocomplain on websites and blogs

  21. westport is no different from any other suburban upper-middle class american town; you’ll attract what complements you and your family, and won’t/shouldn’t even notice what doesn’t.

  22. The Rude and Smooth

    Westport by far. I grew up here and moved to Texas to attend law school and live there for 30 years. I returned five years ago and I disagree with Thomas Wolfe and my former teacher, Karl Decker, one can go home again. Matter of fact, it is quite nostalgic and refreshing. Certainly the town has gone Corporate with downtown all chains of big outfits and the traffic is horrendous in comparison, but I find Westport to be a mixture of those who deem themselves privledged and those common folks who work hard, want the best for the children and love the community. Plus, no place is as beautiful as this town in full fall, spring or fall (my Texas thin blood has still not adapted to the winters). I love it here but I think if you have to ask, perhaps it is not the place for you.
    P.S. I think we had this same dialogue some 8 months ago with a gal from Minnesota??????

  23. Westport Realtor

    I don’t think your realtor should be pitting one town against the other. In this crazy market, you should be looking for the best buy for your dollar and long term investment. And I totally agree with the “Rude and Smooth” comment above: “If you have to ask, perhaps it is not the place for you” especially since you lived here at one time.

  24. Terry Brannigan


    Dear former Wesporter…I grew up in Westport right along the strip you can recall so clearly with your eyes closed. I bounced around like many but settled back in Westport about 6 years ago with my wife and 3 boys. Much of what has been written is accurate, but unfair to ascribe solely to Westport. The negative comments could be applied to a generation vs. a town. Fairfield will never be Westport, but it shouldn’t, each has its own personality and bio-rhythms. It’s great to see Fairfield on the upswing, but simply put, it just isn’t Westport. Nor is Darien. Unlike Westport, neither has a true “Main St”. The fact that Westport has a bonna fide Main St, gives it a heart and soul. Fairfield and Darien have the Post Rd. It’s just a different vibe. I miss the diversity that used to exist in Westport, the demographic has become extremely predictable but there is still plenty to love about the place…including this blog and Woog’s World! Don’t indict the town, indict the generation.
    Conspicuous consumption, entitlement, a belief that others exist to serve and that ultimately their good fortune is solely the result of talent and DNA and not equal parts luck and timing is a generational affliction not a Westport phenomenon. ST Paul’s School is a treasure, so is the staff at Long Lots, we have the Playhouse, Long Shore, Old Mill Beach, Saugatuck and plenty of artists within our sub text. Cowboy up and move to Westport, sounds like you’d be an asset. PS: You never hear Westport claiming to be as good as Farified!

  25. Cranky Old Man

    We don’t want you! We have enough mindless judgmental idiots looking to compare everything before they buy anything. Go to New Canaan. You will fit right in there.

  26. Bobbie Herman

    I have to put in my tuppence.

    Having lived in Westport for 18 years (and my husband for 30), we moved to Fairfield in 2001 because we wanted to downsize and couldn’t find a smaller house in Westport. The builders tore them down before they were even listed!

    We moved about 1/2 mile away from our former house, which was on the Westport/Fairfield line. This was very traumatic for me as I was very involved in Westport activities, such as the Democratic Town Committee and the ZBA. We tried to get involved in Fairfield, but for some reason never felt comfortable. We still do many things in Westport — shopping, library, Westport Woman’s Club, Y’s Men and Women, etc. etc. In fact we do practically everything but vote (and sleep).

    But there is a difference. For one thing, it’s really much prettier where we live — more trees, winding roads, and much quieter. We do go to Fairfield quite often — there are many more restaurants, especially “moderately priced” ones, and movies, of course. There are quiet beaches, as well as crowded ones — you have a choice of five.

    Not having school age children, I can’t comment on that aspect. As far as property taxes go, the mill rate is higher, yes, but the houses cost less, so your taxes will be lower.

    My husband says we have the best of both worlds.

    If you are planning to move back, I would suggest looking at both towns. Fairfield is definitely less expensive for similar properties, and the schools are good. The population is twice as many as Westport has, and I don’t get the sense of community we had. There are definite trade-offs — you have to decide whice are important to you.

    Good luck!

  27. I wasn’t going to reply. Enough has been said. But I didn’t want “Cranky Old Man” (tongue in cheek?) to be the last one to comment. So here goes: I grew up here. Graduated from Staples in ’72. Moved back in ’95 to be near my mom after my dad died. Yup, it’s a different place. The McMansions don’t thrill me. The entitlement-vibe of the rich newbies embarrasses me as well. That’s all been said. But as has also been said, the taxes are lower here than in Fairfield. Plus, the town has many jewels. There’s Dan. 🙂 There’s Julie Belaga. There’s…well, you get the idea. Not to mention, the beaches, the Playhouse, the Senior Center, the wonderful library, the Levitt Pavillion–I could go on and on. You might not be able to go home again–the story of our lives is played forward, not on rewind–but, for me, this sure ain’t a bad place to come home to now.

  28. Westport is an amazing place. I also grew up in Westport and have seen many changes. My children attended Westport schools. Now that they are grown I have a new appreciation of the Town. I play tennis at Longshore and have met many nice ladies by joining the Westport Tennis Association. My husband and I love our weekly dinners at Compo Beach watching the sunset. Westport REALLY does have a lot to offer.

  29. Suzanne Taylor

    Wow! What a question… I have been here since I was a junior in High School. I really don’t want to live anywhere else. I would say there still is a balance like any place else. I have to say it is a caring town, lots of organizations to help people, animals, etc. I think you can find what you want to. If you are looking to elite, stuck up, entitled people, you certainly will find them… lots of places. lol, but i think there are a lot of other kinds of people here too. there are even poor people… lolol me included. I always tell people who are impressed with me being from Westport that I am one to the 10 poor people here. lolol. Anyway, the beach is still wonderful, the schools are top notch, and I’m sure you could find a nitch. SKT

  30. J. in Minneapolis

    Like the original questioner, I too am thinking of returning to the east coast and am eager to hear current Westporter’s impressions. You’ve all given me a fascinating kaleidoscope, which taken as a whole adds up to an “honest” answer. Yes, of course some of the same things could be said of how most upper middle class towns in this country have changed in the last 40 years — such as Scarsdale, NY where I grew up. But I found those willing to focus on specific characteristics of Westport and the comparisons to surrounding areas informative and enlightening. What was not useful was the truly snobbish idea that “If you have to ask, then maybe you shouldn’t move here.” That defeats the whole purpose of communicating on a blog in the firs place. By the way, I was actually colder living on the Upper West Side of Manhattan for 21 years, with that raw wind coming off the Hudson river, than any of my 5 winters here in Minnesota.

    • Richard Lawrence Stein

      J you are correct as a former Upper Westside guy and still a current visitor the windvthat howls off the Hudson is brutal to severe at it’s best

    • Rude and Smooth

      No, actually you are mistaken. Communicating on the blog is to make one THINK. It is not “Dear Heloise” And it remains my belief that if you grew up here and have to ask whether or not to move back, then you are not thinking. Westport is a very special place but because it has senior centers, soup kitchens and homeless shelters. If you didn’t get that the first time around, maybe you should look to New Canaan or Darien. And I spent a winter in Farmington, MN. The temperature never got above 10 degrees. And last time I looked, we, in Westport, are off the Sound not the Hudson.
      There is no comparison in winters.

  31. And the comments keep coming. This is awesome. What a diversity of opinion – which, in the end, is what Westport is all about, right?!

  32. Rude and Smooth

    Diversity of opinion, yes. Diversity of ethnicity, no. And this is one reason why Jeffxs (above) is correct in his supposition that Staples is overrated. Guys, the world ain’t 93% honkey. Bus in a few hundred Blacks and Latinos from Bridgeport this Wednesday and then maybe we are talking Blue Ribbon.

    • Diversity is a two edged sword. If a school population is as diverse as the population in general, then it is average. In addition, there are components of the overall population that most of us would like to see underrepresented; criminals among them. The Westport school system is full of students who rank far above the population averages in most metrics of intelligence and socialization. It should not be surprising then that the graduates of the school system are similarly highly ranked in those dimensions. The real issue is how much difference did this particular schools system make. The same situation exists in many areas populated by residents who are drawn from the upper reaches of the income distribution. Are Westport schools particularly adept at producing well qualified graduates? I don’t think the schools here are any better than the schools in Weston, or Scarsdale, or La Jolla, or Ridgewood, or any similar town. The raw materials in each case, the students, are the true drivers of superiority, not the schools.

  33. Thomas Wolfe said it best in the opening lines to “Look Homeward Angel”

    “…a stone, a leaf, an unfound door; of a stone, a leaf, a door. And of all the forgotten faces.
    Naked and alone we came into exile. In her dark womb we did not know our mother’s face; from the prison of her flesh have we come into the unspeakable and incommunicable prison of this earth.
    Which of us has known his brother? Which of has looked into his father’s heart? Which of us has not remained forever prison-pent? Which of us is not forever a stranger and alone?
    O waste of loss, in the hot mazes, lost, among bright stars on this most weary unbright cinder, lost! Remembering speechlessly we seek the great forgotten language, the lost lane-end into heaven, a stone, a leaf an unfound door. Where? When?
    O lost, and by the wind grieved, ghost, come back again.”

    In other words, “You can’t go home again.” That is also the title of a posthumously published book by Thomas Wolfe!

  34. You’re right that Staples is not diverse ethnically or racially.

    Neither is Ffield, Weston, Wilton, NC, Darien, etc. The only really racially or ethnically diverse towns in the lower county are norwalk, bridgeport and stamford. So unless the woman is considering those 3 cities, the racial/ethnic diversity issue is not one we should discuss really…

  35. Try Weston, lower Weston….all the conviences of Westport without the drawbacks of Westport.

  36. Wendy Crowther

    I’ve lived in Westport for 38 years – graduated from Staples. My family moved here from LI and I never looked back. You’ve heard a lot about what NOT to like. Here’s a sampling of my Westport life this weekend. It may give you a different perspective.

    On Friday, on a break between work appointments, I stopped at Dunkin’ Donuts to pick up a cup of coffee, then planned to head to Burying Hill Beach for 45-minutes of peace and quiet. The coffee-jockey at DDs said, “Small, just milk, honey?” and I said, “Yes, please.” How does she remember my usual order in an endless stream of patron-requests (and I’m there only about once a week)? That always fees nice.

    As I left DDs to head to my car, I noticed a woman in the parking lot wearing a Westport Town Farm t-shirt (the new town farm at Wakeman). I commented about her great t-shirt. She and I struck up an impromptu conversation about the project, about GVI (Green Village Initiative), and the great things they are doing in town. It was a nice neighborly chat with a total stranger. It’s not common in Westport, but it often happens when I decide to start the conversation.

    When I arrived at Burying Hill, the sweet retired guy who has manned the entry gate for the last few years (at least) greeted me with his usual earnestness to check my sticker, and to let me know there was no swimming that day (storm-water run-off into the Sound had spiked up bacteria counts). That was okay, I wasn’t planning on swimming.

    As I sat in my car sipping my coffee, I melted into the view and the serenity. I was the only one there. An osprey flew over the marsh, fishing boats trawled offshore, the sun sparkled on the waves, a breeze blew through the windows. Gorgeous. As I sat there, two walkers approached and paused briefly. One told the other about the scenery and stately homes that can be seen from the beach. As they departed, the apparent guest said, “This is such a beautiful place to walk.”

    On Saturday evening, I met friends at Compo Beach for a picnic dinner. It was a stunning night and the beach was packed with people doing the same. The sunset was amazing, and by 9:00 pm, the moon was rising off the tip of Sherwood Island – a huge orange ball. We all said out loud to one another as we sat on the beach that night, “We are so lucky to live here, and to have scenes like these at our disposal.”

    Sunday I went to Westport’s Farmer’s Market. Tomatoes were exploding out of Belta’s farm stand (one of the only farms left in Westport), and their zinnias were beautiful. I bought some fresh food and talked to Chef Tor Sporre who offered cooking and food advice.

    I then went to Westport Hardware (near Ed Mitchell’s) to pick up a small item. The folks who run the place are so incredibly nice and helpful. They’d practically sold me a new grill before I’d left the place.

    My next stop was going to be Stew Leonard’s but I got stuck on the Westport Bridge as traffic was held so that thousands of motorcyclists, who were raising money for a cause, passed through the Post Road intersection on their fund-raising loop. I did a “yew-y” and headed home. Sure, I was inconvenienced, but it was for a good cause. I hit Stewy’s later in the day via a nearly deserted Post Road. It turned out to be the better plan.

    Yeah, I have my days when the “new Westport” bugs the hell out of me. But then I have days, like those described above, when I feel so fortunate to live here. Some of those days come along when I am volunteering on a town committee or commission and I am out there walking the talk to help make this town a better place. And that’s where I often find some terrific Westporters doing the same. Other good days come along, just because…well, because they do.

    Westport has it’s problems – you’ve heard about most of them in the comments thus far. You’ll also find some great things here, but you’ll have to create them, and notice them, and pause long enough to appreciate them. There are good people to be found here, and you’ll find them when you say things like please, and thank-you, and hi, and is there something I can do to help. Those who don’t answer, and rush past you to their next errand, job, or appointment, are the people you can skip.

    Westport will be what you make of it, and what you bring to it. Remember that no matter where you go, you will always bring yourself. You’ll make your own good times here if you look for them.

    I hope you find what you’re looking for.

  37. Jim Goodrich


    You live in the Westport I’ve lived in for the past 30 years!

  38. Dan interviewed me on this exact subject for his Westport News column, “Woog’s World,” in 2000 at a time when Martha Stewart was leaving town, and I was returning to Westport after my wife and I sold our apartment in NYC. Dan, if you have that in a version that can be posted online, please feel free to do that; I don’t have the article.

    To try to put things in perspective, I wanted to convey something I told Dan for his article. I was talking to a woman in the administrative offices at Yale who learned I was from Westport. She told me that she had lived there and what a beautiful town it was. But she said that, unfortunately, the town had been built up too much and there was too much traffic, so she decided to move. I asked her when that happened; she said she moved out around 1954. By the way, this conversation took place my freshman year of college, in 1971.

    So, the more things change……

  39. Dick Lowenstein

    One subject that has not been discussed is town government. It’s honest, open, and accessible…some say too accessible. Take two Westporters dicussing a subject and you’re likely to have three opinions.

    • That was a joke right? The town government is a bad joke. The town is run by the employees. Elected officials are grossly incompetent. BTW I did mention the town government in an earlier post.

      • Dick Lowenstein

        Thank you for the “compliment” …..if you think we are incompetent, run for local office and become part of the solution. Or follow your own advice, and move and see if the grass is really greener elsewhere.

        • There is clear evidence of incompetence, and the “if you don’t like it move” ploy went out in the 1970’s. As for running for local office, the residents of Westport have revealed their preferences and they prefer incompetence. They prefer a local government that bans plastic bags but can’t control spending and rolls over for all manner of exorbitant compensation demands on the part of town employees. As I posted earlier, local government provides an endless source of amusement.

          • John McCarthy

            Black/White, Good/Evil, Incompetent/Competent, Perfect/Imperfect……I like to think I left that type of all or nothing thinking back in my youth, although it can creep back in. While we may not always get everything right, the vast majority if not all, of those volunteers who are in elected or appointed positions in town are diligent and do what they think is best for the town. I echo Dick; If you don’t like how things are being done, run for office or ask to be appointed to a board or commission.

        • No thank you. I would rather be trapped in a burning building. I have participated in the governing process in Westport. It is foolishness from top to bottom. Are the costs of running Westport under control, reasonable? Are town employees virtually ungoverned? The town did spend $10 million or so for a dog toilet. The geniuses who run the schools shut down schools and then spent tens of millions of dollars to reopen them. We do have a ban on plastic bags, and the town has eliminated courses in physics and math so a course on mural painting can be added to the Staples curriculum. ( A first rate school system indeed!!!) It is good to see that the dim lights who lead us have their eyes on the ball.

          • So why haven’t you moved out of this town yet? And what do you like about Westport?

          • Its clear the town has different priorities then you…it seems as though you don’t like anything the town does, so why keep complaining? Either stop criticizing everything about Westport (the schools, the government, our plastic bag ban), do something about it, or leave. As a student, I’m pretty sure our physics and math classes are still here, and why can’t art be just as important as these classes? Our students strive in almost every possible academic field I can think of, so if someone wants another art class, why not? I believe a first rate school system should have a wide range of different classes. If you want to do something about it, then try joining the board. It seems like you have all the answers, so go for it.

          • Red and Blotchy

            Stick to your guns, Jeffxs. Actually I find this entire dialogue rather silly and pretentious. Do we really need 70 or so blog entries on how wonderful this town is??? To me, it is truly a remarkable place but not for most of reasons specified above. As the immortal Paul Newman once said: “It is a privledge to live in Westport.” And it is so, not because of the wealth, macmansions, “super” (sic) school system or any of the other aforementioned fluffy showey transparent things that affluence brings to a town but for the compassion of its residents. The people make Westport. Not the other way around.

    • The sophomoric responses to my criticisms are to be expected; the emperor’s new clothes and all. Westport is no better and no worse than any number of towns in the New York SMSA. It is amusing to see that not one of those who claim to be part of the governing elite have taken issue with my specific criticisms; the town budget is out of control, the employees run the town, the schools are no better than those in many similar communities, and yet the costs of the schools rise beyond reason. The citizens are pretty typical of those in many other nearby communities. Why move? BTW I would suggest that anyone who has not read Alexis de Tocqueville’s “Democracy in America” do so. He explains why the best and the brightest in America do not seek out public service. Westport’s office holders are what is to be expected.

      I am in the process of of obtaining a Florida residency for the time when my wife and I retire. I don’t see why any sane person with an estate or income would want to be a CT resident unless necessary for employment purposes. On a larger scale,perhaps the ruling caste can explain why CT ranks near the very bottom in private sector job creation and population growth for the alst 20 years.

      • The Dude Abides

        Agreed on the analysis. Westport is not “special” but a pretty dang nice place to live and grow up. We are basically semi-retired and wrangle every year whether to get out or not. I note that the cost factor was/is never brought up in the comments hereto. It is expensive to live here in comparison to other parts of the country, especially for our lass from Minnesota where it is probably 1/3 of our overhead. But Florida?? Jeez, can’t even get an election right. Upper outer banks and east Maryland are places we are looking. Just as pretty views with 1/2 the cost of living. Keep up the good fight. Those sophmoric responses are based on pride, fear, “going with the flow” and many times, just being argumentative. You bring a fresh voice to this blog which scares people.

        • My question was: Why haven’t you moved?

          I didn’t give him a sophomoric response in anyway. I don’t agree with everything he says but I am smart enough to know that Westport is no where near perfect..

          I have gotten to agree with lots that the Dude has said lately though

  40. Having been born in Norwalk, raised in Westport ( with two family businesses on Main St.), graduated college in Bridgeport and lived and raised a family in lower Weston, I believe I know a fair amount about Fairfield County. I can add little to the diverse opinions above, but if you’ve been away for awhile the reurn can be a little jarring. The Main St. of small, friendly family owned stores has morphed into BananaRepublicGap for the Entitled. The local soda fountain has been replaced by Starbucks. The Fine Arts theatres have all gone. The Playhouse has lost its charm but is more user friendly. Westport’s “other” wonderful live theatre, WCT (Westport Community Thratre) is excellent and thriving. The tempo is faster, too many folks tense and unfriendly. But the same can certainly be written about all the so called
    “affluent” towns along the Commuter Coast. I found lower Weston the better choice. Shop and dine in Westport, live more leisurly with friendlier neighbors. And it’s only an extra 3 or 4 minutes to the train. Good luck.

  41. I grew up in Westport at 28 Hillspoint Rd. I went to Hillspoint, Long Lots and Staples. My two daughters went to Greensfarms. We all went to Saugatuck Nursery school. I would have to say I spent a total of 34-35 of my 41 years in Westport. Been a child there and had children there.

    Westport has changed. It is not like it was in the 60’s and 70’s. Not even the 80’s. I remember Big Top, Bonanza, the Remarkable Book Store, the A&P, Arnie’s, the bowling alley, seeing The Yellow Submarine at the Westport Playhouse when I was 5, seeing Star Wars 30 times at the theater where Restoration Hardware is now, my first job was sorting books at the library before it was Starbucks, the farm stand where the Lexus dealer and the condos are now, the Stew’s milk machine down near the Saugatuck train station, hanging out at the DQ, Allen’s Clam House, when the water was clear at the beach….

    Back in the 70’s and 80’s there were more homes that average joe’s could live in. And there were average joe’s. Not everyone drove a Range Rover or a Beamer. I didn’t have a TV in my room or a laptop or a cell phone. I didn’t have my own car. There wasn’t as much flaunting of wealth as there is now.

    Last year I went into foreclosure. (it sold a week prior to auction!!) Single mom with two eelementary school age kids. I tried. But the more I thought about it I came to see it as a blessing and a release from the endless cycle of spending. My folks have an Inn in Maine on Mount Desert Island. They suggested I move up there and help them run the . So that’s what I did and that is where I am right now. And I can say with no reservation it is the BEST move I ever made.

    The pace here is slower and the people say hello and smile and wave every day. There aren’t endless stores to throw your money at to distract from the things that are of real value. Like spending time outside and with your friends and family.

    My advice is to not even move to CT. Maine is great! NY state is nice too, as well as VT and NH. If you have to move to FF County or that area I would suggest look in the Redding, Bethel area. If it has to be around Westport I’d say Stratford.

    The stress level and the hyper energy in that area is high. There is no way around it. And the people are about money. I wanted my kids to liuve outside the biubble like most people do. I think it serves them better in the long run. Up here my daughter is skipping a grade and won a Maine writing contest. She has 13 kids in her grade. Yes, garde. And all the kids get Aplle lap tops through school. State law. There are other places where people are real and don’t all own IPods. I don’t have one and I don’t miss it.

    Hope that helps! Good luck.

    • Red and Blotchy

      Effie: Nice sentiments and I as well grew up here in the 50-60’s when everyone did not have to show off their money. Sorry for your downturn but I think you overrate the wealth around here. I bet many are upside down on their mortgages, credit card balances up the ying yang and jobs in jeopardy. A guy down the street lost his job and his kid was driving a Lexus to Staples. A lot of show and not much dough, I am afraid. The American way. Many of the “old school” still around and make the town a joy to me still.

  42. Well sounds like your in my boat only I just moved back a month ago after 13 years away. Plain and simple it has changed a lot. I grew up here for 28 years and it still has some of the charm in places. But I am not liking all the McMansions. As far as the influx of newer people well they seem to have a little less common sense and a little more self entitlement but not a super difference from back in the 70’s/80’s. But really when it comes down to it every opinion will vary and yours is the only one that counts! Good luck on your decision.

  43. Here’s a link to a post by a blogger from 2007 entitled “Changing Westport: a 21 Year Old’s Perspective” which is still receiving some comments. It’s interesting that many on the list have come and gone yet again during the past 3 years alone.

  44. Funny how so many of the comments echo my mother (a 55-year resident): “The cars are too big!” Yes, but how big were the cars in the ’50s? And how big were those Ford and Chevy station wagons that every mom drove back in the ’70s? Most cars are SMALLER today!

  45. We moved here for Longshore and the beach (PUBLIC facilities), the schools, and the library. I haven’t been disappointed on any of those measures. Longshore and the beach are a pleasure year round, the schools have been great for our four kids, and the library is the place in town to find any book and any movie, meet up with friends, have a coffee, or just hang out reading. We’ve made great friends, we love the green vistas when driving, and we stay civil in our cars, at all times — no matter who we might encounter on the road. I just wish it were closer to NYC….

  46. Max Stampa-Brown

    It ain’t half bad, beautiful to say the least.

  47. I love Westport…We have lived here for 43 years on Saugatuck Island…maybe that is why that is why it has been great although we are in the process of getting sewers (finally& great news) & have rough roads…but WHAT WE DO HAVE IS: Over 105 private residence families living just over the one lane bridge; we have are own beaches both north & south, a boat launching facility, have a 4th of July Parade & Pool party, which I still lead although on a convertible, ….our own Saugatuck Island Resident directory & a December holiday party & an park at the entrance, thanks to one of our members. There is a fabulous mixture of the young & old…& there are homes for sale, so come join us…it is a paradise for raising a young family & there is nothing like looking out to the Long Island sound toward cockenoe island any moment of the day….That is just where we live…but the town has everything…amazing…. A very grateful Betty Lou Cummins