Should This Woman Move To Westport?

You won’t believe the stuff that pops into my inbox.

The other day, a very cool-sounding woman emailed me. Long story short: She’s a native Californian who spent the last 7 years in Greenwich Village. She’s a freelance graphic designer, with a great portfolio.

Greenwich Village... (Photo/Loolie)

Now she, her husband and 2-year-old girl (who really has no say in the matter) are thinking of moving to the ‘burbs. They’re looking at a couple of places: Westport and Darien.

She searched the interwebs for “writers or passionate Westporters who could enlighten me on what to look forward to, or what I’ve been missing.”

Ta-da:  “06880”!

I could talk all day about Westport: the good, the bad and the truly bizarre.

...or the village of Westport?

But she was looking for Westporters — plural — so let’s open it up to “06880” readers. You guys never lack for opinions.

Just click “Comments,” and let the fun begin. Should this arts-oriented woman — and her husband and little kid — abandon New York City for Westport?

What will she find here? What will she love, or loathe? If you had it to do over again, would you?

And on and on.

Be truthful. Be real. But please, be fair.

140 responses to “Should This Woman Move To Westport?

  1. She couldn’t do any better. End of story.

    • The Dude Abides

      Wreckers v. The Blue Wave
      Bedford Middle v. Middlesex (!!!!)
      Compo Beach v. Weed Beach & Peach Tree Rock Fest
      Sherwood Diner v. Sugar Bowl
      Longshore ($) v. Weeburn, Woodway & Darien Country Club ($$$$$$$$$)
      Westport University Library v. Darien Hole in Wall
      Downtown on the water v. Underneath the RR Trussel
      No movie theatre v. 1945 Edition.
      Downtown YMCA v. . . . . . forget that comparison
      Compassion v. Snobbery
      Man in the Grey Flannel Suit v. Gentleman’s Agreement!!!

      • The golf is definitely better in Darien, I would leave that and the Y comparison out.

      • First landed in Westport 4/6/77

        Dude, if you’re not willing to take a trip to the Darien Library, you might consider editing your comparison. You’re driving with an old map on this one. Both libraries are excellent, and Darien’s is newer, built with funds raised before the 2008 collapse.

      • The Dude Abides

        Weeburn is $250,000 up front versus $70.00 for a golf pass at Longshore. And how many Brian Claar’s does Darien have/had on the PGA tour??? I rest my case.

        • Richard Lawrence Stein

          I’m with you Dude!!! The golf is a ridiculous comparison…. Big fat 0 for public use… but they have a great library it is pretty dam awesome…

          • The Dude Abides

            I have done extensive research projects in both libraries. Westport is, by far, the better. With libraries, it is not just the bricks/mortar.

            • Do people still do reasearch in libraries? It seems like a very inefficient method for gathering data.

              • The Dude Abides

                I am the model of ineffciency. But not everything is on the internet. Old newspapers for one.

        • With the new $300,000 hot dog stand Longshore will have facilities second to none; if you don’t count the driving range.

          • The Dude Abides

            And we can enjoy the facilities even more now that it will take 5 hours to play a round, including 1 hour for lunch at the 9.5 stand. Do you think they got the name from the price of the dog? $9.50?

          • your driving range sucks horribly.

  2. Outstanding school system, Compo Beach, Winslow Park, the Westport Country Playhouse, Levitt Pavilion, LeFarm, The Dressing Room, Sherwood Island, Wakeman Town Farm, Westport Farmers’ Market, Earthplace, etc. The list is endless. And you can farm your land, raise chickens, do the whole “homesteader” thing. Westport knocks Darien right out of the park.

  3. Ever watch the show suburgatory?? Stay in NYC unless you are looking for a “group think” mentality from mothers who don’t work. Not saying Darien is better, as they come, WESTPORT IS A TOP NOTCH BURB, but don’t kid yourself… It isn’t NYC.

    • Advocate of public education

      wish I agree that the school system was outstanding. 2 to 3 years ago, i would have said this was the case. Budget cuts have taken their toll. Ask any teacher or child what its like to be in class-room of 24/25 kids!!! Buyer Beware!! In terms of everything else.. Agree fully. A truly great town to live in.

      • Except that Staples HS was just ranked #1 in the state of Connecticut, Coleytown Middle the #1 middle school. Did you notice that the median home selling price went down from 2010 to 2011 in every Fairfield County town except for Westport? One reason: the schools. Kids get the equivalent of a topnotch private school education that would cost big bucks in NYC, for only the cost of one annual real estate tax bill. So those of us who no longer have kids in school, or those who never did – still get great value from the exceptional quality of our schools. PS After my 3 sons graduated and went on to college, they all found the academics easy their freshman year, compared to Staples.

        • You don’t want to push that too far; Staples is good but not as good as a topnotch private school. Moreover, US News does not rate it as the top HS in Connecticut. A visit to the schools in each town under consideration, might be the best way to get a sense of how each school sytem might fit your needs.

          • Another anonymous...

            Knowing what I know now, If I could afford it, i would send my kids to private school. Kids who are high achievers do well at Staples. Staples has something for everyone– if you are talented– regardless of the talent. But if you are an average kid, or a kid who struggles– you don’t get the attention or focus you would in a private school.

            • Couldn’t agree more, Another. And it’s not just about talent. If you’re a kid who doesn’t enjoy competition on all fronts, from academic to physical to social, Westport schools are a challenge.

              • Richard Lawrence Stein

                You better have your child live the rest of their life in the cave bunker you are creating for them….Life has competition all the way through it…. Are you going to hover and kiss their boboos in college…are you going to interview for them after words…or for their internship…oh sorry thatr is a competiotion too…. come on now….. Staples and College and anything in the world in many cases is WHAT YOU PUT INTO IT< IS WHAT YOU WILL GET OUT OF IT….. FOR THE REST OF YOU YOU ARE RIGHT STASPLES IS NOT A PRIVATE SCHOOL!!!! YOU WILL NOT GET A 40K BILL!!!! BUT YOU WILL HAVEW SOME AMAZING OPPORTUNITIES…. IN MANY MANY AREAS BY SOME AMAZING TEACHERS AND EDUCATORS….

                • @ Mr. Stein, Yeah, that’s what I used to think: Public schools prepare kids for life. But if youngsters are thrown into the deep end of the pool too young, many will struggle (or sink). My eldest, for example, thrived at Staples. My youngest…not so much. Why? Because, contrary to what some of us want to think, not all kids are above average. Not sure how old your kids are, but the level of alcohol abuse, pot use, cutting, computer/game addiction, anorexia, and CHEATING — among both underperforming and high-achieving Staples students — is astounding. And that’s before counting the number who are on psychotropic drugs or in therapy. A little competition may be healthy. Too much of it too early is not.

                • Whatevever competition exists at Staples; it is akin to the minor leagues when compared to the typical boarding school in the Northeast.

                • Richard Lawrence Stein

                  Myself and mysiblings all graduated from staples all those things have existed back in the day

                  • My point is that Staples is the icing on the competitive cake. For my second child, the debilitating social pressures started in second grade. Shame and academic insecurity in fifth. By seventh grade, he got the threats/dire warnings about how tough things would be in high school. I don’t mean to say it’s the “fault” of the schools, or that it’s not just as bad, or even worse, in other places. Only that “great schools” is a double-edged sword if your kid’s not an early and enthusiastic bloomer.

                    • The Dude Abides

                      Well it is not just for the youngin’s. Check out the faces of a lot of Staples juniors who have just gotten their SAT scores back and realize for the first time in their life that they ain’t going to Dartmouth like Mommy/Daddy. I gotta tell you it is downright sad. And that is where I find fault with the school system. It just furthers the over-expectations of the parents. Some kids thrive, the majority do not meet those high goals.

        • Advocate of public education

          Jessica– get current!!! the schools your sons attended have changed. Not across the board– I have to say on the whole they are excellent, The teachers are devoted and passionate, everyone tries. However– budget cuts took their toll. If teacher/student ratio was restored prior to severe cuts school had (had no choice, I realize that) then– i would say– this is the best place to live. But– I hear Staples parents complain about large class sizes too– its an issue.

          • “Severe cuts” when, where, be specific. When has the budget been cut by as much as 1%? Expenditures have not been cut.

        • I don’t think you are in a position to comment accurately about Staples today. The climate in general is alienating and cutthroat. A group is hoping to organizing to speak to Dodig about this but he just wants to promote and see the positives and not the ugly side of this school. Many kids that the we have spoken to feel pressured from the culture there as well as from teachers and coaches and, of course, colleges and parents. It’s nowhere near a perfect school. The only reason the schools here rank high is from scores. That is what is judged. The teachers teach to the test Coley Middle is academically abysmal. The teachers are burnt to a crisp and the principle, psychologist and guidance staff is mediocre at best. There could not be a less inspiring curriculum than the entire Westport School district’s. I have tried to change and give ideas to no avail. They want to teach to the test for real estate revenues.

          So, to the COOL WOMAN who wants to move here, if you want a creative community for yourself, you will be disappointed with the mothers devoted to their bodies, not their minds. And you will have to supplement your kids education with numerous trips to the city and beyond. YOU will have to teach them to think critically. The schools will fail you on that. And make sure you thicken their skin and raise ther self esteem sky high so that by the time they get to Staples they do not get beaten down and sucked into the culture of thinking they are not good enough if they are not ____________(fill in the blank: the smartest, most athletic, good looking/ pretty).

          • Richard Lawrence Stein

            Realist? Really!!! Are you at the school… I am there enough and around many different students and you could not paint a picture so more wrongly.

            • In answer to your question – yes. my kids are there and i am involved closely with them and several other students. we have an ongoing dialogue about their experiences. all are unique to the individuals but there are central themes.

              Retract your claws – i was responding to Jessica Bram whose kids have since graduated.

  4. Please…Tell the lady to provide a photo and bio of her family. DOB and where in California she’s a native. Need hubby info too. I’m a trifle concerned about anyone who puts Westport and Darien in the same league as a town to live in. Soon as I get more info I’ll be able to advise her.

  5. Darien is the better choice by far; great schools, less acrimony, good clubs if you want to play golf, closer to NYC. Westport is a poor man’s version of the Upper Westside. If she want that ambiance, move to NYC.

  6. Richard Lawrence Stein

    First and foremost nothing is NYC!!! And even more so nothing is Greenwich Village/NYC!!! There is not 24hr delivery of food, their are no sidewalks to go wandering for days, weeks, months, or years… It is in comparison not remotely close for the diversity or constant stimulation mentally, physically, or emotionally.

    With that said, I have lived in Westport for several decades and have participated in most every aspect that can be offered to one at each age… Plenty of sports, arts, culture, and other involvements… You have many fun things to do between Compo and Longshore… We also have Earthplace… And yes the schools, the downtown, the easy access to get back into the city, or explore the rest of lovely New England.

    In regards of Darien I have and had spent much time working there over the last 12 years. The beaches are small.. The parks are small… There is no public golf course…. The downtown area is a nightmare on a good day… Let’s just say the residents are nice and pleasant but extremely cookie cutter in appearance…

    Your background is design and art? You could not honor the history or designers more so then coming to Westport.

  7. Elisabeth Rose

    Unless you’re single, there is a lot to offer in Westport, not the least of which is its location on the Sound, as well as its proximity to so many areas for outdoor activities where you can kayak, row, hike, ski, etc. and still only being an hour from NYC. For someone who is an artist, there is the Westport Art Center, Silvermine Art Center in nearby Silvermine (Norwalk) and other places nearby to take art classes or see art. There are many places to go with or without children: the beach, park, lakes, downtown, the library, Longshore, restaurants, gyms, all sorts of exercise centers (swim, row, sail, play golf, climb walls, play tennis, do yoga, dance), theaters, places to take classes. There are tons of places that are geared to kids of all ages, such as the kids’ areas of Compo Beach (jungle gym, etc. for little kids; skateboard park for older ones), Earthplace (the nature center), the Y, dance places, art classes, theater and choral groups for kids, and the list goes on and on. In nearby towns there are others: the Maritime Aquarium in Norwalk, Stepping Stones Museum and Beardsely Zoo in Bridgeport, the New Canaan Nature Center, the Bartlett Arboretum, and Silverman’s in Easton (great for apple-picking and hayrides.) I’m sure I’m only skimming the surface of places for kids…

    To people coming from NYC there will definitely be some adjustments. Having lived in the city for almost 18 years, the drawbacks for me have always been Westport’s homogeneity and the fact that there is almost no nightlife. (While these are things I dislike, someone else might like them…) Also, there is limited public transportation. (Unless you’re on the commuter van at rush hour, you will only see the occasional inter-town buses.) Few people walk, because things are farther apart, and unless they are joggers, most of the folks who walk are the hired “help” or migrant workers who may not even own a car. (This clear distinction of class and race is always something that has rankled me… Often the only people of color one sees in Westport, w/ few exceptions, are those waiting for a bus, working for others and/or bagging groceries somewhere..) In terms of getting to know people, you need to be more proactive, since you aren’t bumping into your neighbors every day as you’re more likely to in the city. Also, one of the features I used to love about Westport is gone, and that is Main Street, which used to have individually owned stores, a movie theater, cafes but is now an “outdoor mall,” like so many other town centers in the U.S. Although NYC itself is suffering from the same chain store takeover disease, fortunately it still retains mostly individually operated businesses.

    Westport is so different from NYC, it’s hard to compare. No place has the wonderful energy the city has, but if you’re looking for a nice place to live that is less preppy and a little more artsy than, say, New Canaan and Greenwich, with more citizen involvement than many of the small coastal towns, this is it.

  8. Elisabeth Rose

    Some more positive things: Great schools in Westport and yes, growing awareness and activity around the need for fresh food, with a burgeoning community garden and many farmer’s markets.
    More negatives: A pervasive sense of entitlement from many (which is also in Darien, New Canaan (in spades) and many other similar suburban towns outside of NY.) And often it is hard to see between the cookie-cutter suburbanites w/ their green chemical lawns (A weed? God forbid), their McMansions and (for women) French-manicured hands w/ huge rocks to find some of the more individual artistic types who used to dominate Westport before it was indundated w/ “new money” twenty-thirty years ago.

    Just a thought: If you (the people thinking of moving here) have the money to move here mostly because you want a bit more space and green grass, why not look into a Brownstone in Brooklyn or the Bronx? You can be in the city with all it has to offer and at the same time have a yard and be farther out if you want to go away… Other options might be Chappaqua, Katonah, Irvington or other little towns that are closer to NYC and not as “suburban” in feeling.. (although they have less to offer than Wstpt in other ways)

    • Richard Lawrence Stein

      You are missing a monster component in this arena… TAXES!!!! A home of equal value in NYS is going to have a tax bill that two to three times more than it’s CT counterpart. Also insurance rates!!! Just putting it out there!!!

  9. Oh please, don’t make her feel unwelcome.

    • Elisabeth Rose

      No one is making her feel unwelcome. She asked Dan to get our opinions. Actually, I selfishly would LOVE to see more artists up here. But the woman asked for our feedback…

      Every place has its pros and cons, and those of us who have had the wonderful experience of living in NYC as well as Westport can at least offer some comparisons.

  10. I like the way this woman does her homework! Finding Dan Woog to help in this decision is brilliant and creative. Brava.

    I do think, though, that the decision to leave NYC is a very personal one. There are so many little details about living in the suburbs that I love and there are times when I miss living in NYC so intensely. Since the above posts have already covered a lot of ground really well, here are just a few little details that I’ve noticed that make me miss NYC:

    – Driving everywhere, especially in the winter. Getting into a cold car, worrying about whether the snow will impede your ability to get to work, sometimes driving somewhere just to take a walk.

    – My subway commute. I used to like the little walk to the subway and seeing a wide variety of people — people of all colors, backgrounds.

    – Wintertime darkness. When I lived in NYC, I don’t recall really caring about how dark it got in the winter. But out here, I really feel that in the winter it is more difficult to motivate myself to get in the car after 5 PM to go out to dinner, run an errand, etc.

    And what I love, in addition to the many great things that have been named by others here, is living in a smaller community where on a daily basis I can run into people I know. I like the ease of living here, the space, and the beauty.

    • Excellent points all, I would concur as someone who lived 13 years in NYC but has lived almost all the time since he left there (?? years) living in the suburbs.

  11. What? Are we really trying to defend where we live for someone doing an internet search as to what town they and their family will move to?

    There are pluses and minuses in every area of the world, otherwise I would still live in LA. Since we are only 1 hour away, it is time for them to hit our streets and find out for themselves what we treasure and disdain for themselves.Hang out at the beach playground, watering holes or coffee shops or attend a town meeting to get a glimpse of the true character of your future home.

    • Hi Mary Ann:

      Sorry if I didn’t make it clear, but this woman has spent a great deal of time looking around Westport (and Darien). Her request to me, and my post, was to solicit even more information for her. It’s great to visit a town, but it’s also nice to hear a variety of viewpoints from people who live there.

  12. Anyone who needs help figuring out which is better, Westport or Darien is already a lost cause.

    • Elisabeth Rose

      Why? Most of us, before we settle in the area, have any idea about differences w/in these little suburban towns, even if collectively they feel quite different than the towns on the Hudson or in upper Westchester..

      • Darien’s “differences” are well known to those who are sensitive to that sort of thing – you know, like, non-white, non-christian people. Not to say that Westport is some mecca to inclusive diversity, but bigotry is not as much in our DNA as it is in Darien – and they like it that way.

        • We are only bigoted towards people who live in Darien.

          • I see what you did there… acknowledging well documented bigotry makes one a bigot … it almost makes the word meaningless. Almost. Why do you think the artists came to Westport?

            • The people of Westport are no more or less bigoted than the people of any other town in Fairfield County. We think our bigotry is justified because we have all truth and justice on our side, and those other guys don’t.

              • Not necessarily true, anonymous (blue). Westport was a welcoming community in the 50’s when many Jews moved here from the city or Long Island. Not true with Darien. They didn’t set “Gentleman’s Agreement” in Darien for nothing. People of color have had diffculty finding a place here or anywhere in Fairfield County because of the cost of living. But in 1964, there was Staples class President who was Black and that has never happened in Darien.

                • The cost of living is in a part a function of zoning requirements. Here in Westport we love our zoning requirements. We don’t like sewers because with sewers comes the possibilityof increased density and,lower priced housing; it is of a piece. We pretend to be without bigotry, but we are not.

                  • The Dude Abides

                    No zoning in Houston but tougher deed restrictions as to color of your house, upkeep of yard, etc. etc. than here. I still maintain that while bigotryis alive and well here, it is cloaked somewhat in acts of compassion. I don’t see any such pretense in Darien.

                    • Some guy in Darien a few years ago asked me, “What is a Christian woman like you doing in a Jewish town like Westport?” I was horrified, and I know that in one school in Darien we visited, only TWO 2nd graders knew anything about Hebrew and the teacher said that there were only three Jewish children in the entire elementary school. I’m afraid that “Gentleman’s Agreement” is still alive and thriving in Darien, IMHO.

  13. jackie gordon

    I would be more that happy to show them houses in Westport –
    jackie gordon

    • Lamplight JD

      I like that……..a realtor who takes advantage of every opportunity!
      Cudos to you!
      I bet you do very well…………..!

      Good luck with this chance to obtain a new client!

  14. Fun posting, Dan. A quibble with your parenthetical aside: The couples’ two-year-old may well have a say in the matter, even if largely non-verbal — especially if they take her to the kids’ playground at Compo Beach, or to the WPL’s Kids Library (and sample a “Rhythm and Rhyme” class there), or visit the Family Y for a parent-child dip in the warm Brophy Pool or a Toddler Adventure Gym class in the Gymnastics Center, or — since they’re an arty family, sampled a toddler art class over at Westport Arts Center. In fact, I’d be surprised if their child’s best interests don’t play a big part in where they ultimately decide to move. Hard to beat Westport on that front…

  15. Since the wife is an artist, I thought I would share the following: I have a very good friend from college who has raised his family–three daughters–in Darien. The kids all seem to have had a happy childhood there and have gone on–or are about to go on–to excellent colleges (Ivies or Littlle Three. And all three are superb athletes who played on state title teams at Darien.)

    My wife and I attended the high school graduation ceremony for the oldest daughter. This took place roughly six years ago.

    One of the senior class speakers was a musician who I recall being part of the school orchestra and/or band. She said something along the lines of she wished students in music/arts activities received the same kind of attention from the community that student-athletes did. It wasn’t the focus of her remarks but, still, it really struck me, because I don’t believe a student speaker at Staples would ever make the same comment.

    I played soccer at Staples over 40 years ago; we attracted great crowds, and so did the Staples Players, the Candlelight Concerts, etc. The bottom line is, Staples was not a jock-oriented school in terms of extracurricular activities back then. I think the same kind of enthusiastic following for the arts at Staples is true today, but I suppose it would be more appropriate for others with kids in the school system to speak to that.

    One more thing–I have friends from my class who became graphic designers and still rave about the art courses they took at Staples back in the day. Again, I think the same kind of devotion to excellence in the classroom to art can be found today, but it would probably be best to speak to parents of current students.

    • Staples music dept gets little publicity other than Candlelight Concert. It’s a major complaint from music students here. Of course there’s lots of weekly news on all the sports teams, wins, etc! Have you read anything lately about the Staples kids who won auditions for Regional Band/Orch/Choir in the fall or All-State ensembles in the winter? Or about the Staples jazz band’s recent jazz festival win in Greenwich? Or anything about the art dept?

      • I don’t look at the local Westport newspapers that often anymore because the local coverage overall has shrunk. But are you saying that crowds do not turn out for concerts or plays? I was to a Staples Players production a year ago and it seemed to be almost a capacity crowd. Admittedly that was just one performance, but the place was packed and there seemed to be a broad age range in the audience, including current students.

  16. If even one of them is going to be still working in NYC I would stay in NYC because the 3 hour + commute will take time away from their relationship, time that they probably now take for granted.

  17. Having grown up in Westport and moved away, never to come back, I wonder why she doesn’t pick somewhere that is not so inundated with New Yorkers? Maybe that’s what she is looking for? The Westport of now is nothing like the Westport of the ’50s and ’60s. All the ‘chain’ stores of NY have moved in and wrecked the ambience of a small town with family-run stores and restaurants. Westport is but a shadow of its former self with all the tear-downs and building of McMansions that are ugly and don’t fit the lots they’re built on. The expense of living in Westport would deter me from ever coming back (all of CT actually). If I had to move back to CT, I would probably choose somewhere further from the city. If she wants somewhere that is still accessible to NY by train, etc. I would probably choose somewhere like Redding, Bethel, or even Westchester County, somewhere on a train line. I just don’t think of Westport as a ‘move to’ kind of place anymore. Our family moved there to make commuting to NY easier in the ’50s. It was different then. Also, there is a sense of ‘entitlement’ that is pretty pervasive. I had a very hard time there as a child, because of kids that considered themselves better than I was – their parents were richer or they were better-looking than I was. I have never again felt ostracized like I was in Westport. Don’t get me wrong, I made friends, but it was generally very hard growing up a shy, sensitive child. Just some thoughts to keep in mind before moving there.

    • I think the new, the revitalization of Saugatuck Area is bringing that area of Westport back to the ambiance that gave Westport it’s former status as a country retreat from NYC. Also, if anyone from NYC does have to move to Westport but still has to commute back to the city, the ability to live in that area and walk to the train, walk to restuarants, walk to banks, etc., is an enormous attribute.

    • A shy sensitive child has a tough time anywhere, don’t you think?

      • I think you’re correct Mary Gai, I possibly could have done better in another town, but who knows? I just know I never felt like I ‘belonged’ in Westport. Never have felt that anywhere else.

        • I wish there was some sort of meter that measures sensitivity. Would solve a lot of problems. As parents as teachers, and as classmates, we’d be much better equipped to handled sensitive kids if we knew. I don’t think people understand it.

  18. With a positive outlook and an upbeat spirit, you will find any town a great place to live.

  19. A word of caution: Hopefully she is not expecting her income as an artist/graphic designer to support living in Westport. Those days of Westport as an artists’ colony are long gone….

  20. 26 years in Westport, went through the entire school system, now putting my kids through, there is only one thing I regret …. eating at Angelina’s! That place needs to close down, it is ruining this town!

    • The, albeit less than a dozen times, I have eaten at Angelinas, it’s always been lovely. The staff is considerate, and the food is homemade, fresh Italian. I can’t imagine anyone having anything to complain about there.

    • John McCarthy

      Wow, congrats if that is your only regret.
      We like Angelina’s, and Westport Pizzeria….

    • I love Angelina’s — the people are super nice, they have tons of regulars, and I suggest the chicken francese and the cavatelli with broccoli. And the funny thing is my children are older now, but when my husband was a hard working finance guy, I, along with my 3 kids less than 2 years apart ate there every Friday night before 6pm (so I wouldn’t have to do the dishes) for years. The staff complimented me on how well behaved my young children were!

  21. Why does one poster always have a hard on for Angelina’s? I haven’t eaten there in 30 or so years but its an innocuous place is it not? Ruining the town? Evidence please.

    • Seth, thanks for pointing out that it’s probably the same “Anonymous” who bashed Angelina’s recently. The only good news is that “any publicity is good publicity” and I hope this will send people to Angelina’s to decide for themselves. I haven’t read any evidence yet from this poster.

  22. Ridgefield!

  23. First landed in Westport 4/6/77

    Darien’s coast can be exceptionally serene when compared with other gold coast towns, but the best parts are far more privately accessed than Westport’s. Westport’s legacy energy and residents have greater eccentricity and ethnicity than those of Darien. Both towns have exceptional four-season natural beauty, abundant commercial offerings, and active educational & cultural lives within the identified limitations and caveats associated with monied, family-oriented suburbia.

  24. Two words: Art’s Deli! That alone should close the deal over Westport v Darien.

    • Lamplight JD

      If that would seal the deal for you, food must be the driving force in your life!


  25. Westport has a plenty of DISKs (Dual Income Solo Kid).

  26. The Dude Abides

    I believe the last gal who wanted to move here and prompted all sorts of comments was from Minnesota. I am with Veteran, I want a complete DNA & criminal background investigation before I advise her either way. But I married into a family from Darien, ARE YOU SERIOUS??? They still have a gentleman’s agreement going on in that snotty suburb and for no good reason. Westport is Westport. For an artist, end of discussion.

  27. Between NYC and a CT-suburb there is also a difference in the intimacy that you share with your neighbors. In NYC, the people who stay there tend to be well acquainted with their neighbors over at least a few generations whereas it seems to me that in the suburbs most people tend to come and go as their children graduate highschool. In NYC you have children walking to school together, older people walking to museums, lincoln center, other theaters, and grocery stores together, everyone of all generations congregating in the parks together. The City offers much less privacy and down-time, and that is just what you gain in Westport, Darien, etc.

  28. Ridgefield, Fairfield, Redding

  29. Mike Pettee

    Dear Greenwich Village residents: I have logged 54 years in Westport and my 6 children had 78 years in its school system. Furthermore, I’m staying here (No “Westport North” aka MeadowRidge). Over the years,I have enjoyed almost all the the positive benefits of a Westport resident cited above and I can still enjoy many of them – obviously @ 80 + I am out of range for many of them. And yes, Elizabeth Rose, I’m single now (although I would rather not be). If Wee Burn is your thing, one of my children is a member and he does not live in Darien. I have a Westport tie from the Darien Sport Shop and I wear it proudly.

  30. I don’t think the comments here are making a good case for Westport.

  31. In all honesty, on this particular site, you are not going to get an objective reaction. Westport will definitely come out more favorable because it is “06880”! Don’t know if there is a comparable blog for Darien.

  32. Old and Grey

    Who cares whether this person comes to Westport. Just gives some of the crowd here another opportunity for displaying their snarkiness.

  33. Old and Grey

    But it is entertaining….that’s why I keep coming back.

  34. Westportmom

    From the comment stream alone, they will be brave to move to Westport. There are a lot of opinionated people here. There is something for everyone in Westport and in the Westport Schools. Try to live near the beach. Check the public schools. The private schools are fairly small-minded.

  35. Talk about ironic. Today I spoke with a DAD from Darien who just joined the Westport YMCA because they did away with their squash courts in Darien and his son loves to play the game.

  36. Welcome to Westport

    Dear Freelance Graphic Designer,

    Elisabeth Rose’s “cookie cutter” and snarky McMansion post is not reflective of the newer Westporters that have been here less than 30 years (at least the ones that I know). If you move here, you’ll probably meets tons of people via your child (or other activities you may become involved in here). Yes, most of the other parents will be newer to the town, and some may live in newer, expensive homes. Some may have really nice lawns (a comment on that later). I’m not sure which type of house you will be in, but that doesn’t really matter because the vast majority of the newer Westporters won’t really care and will accept you for who you are and not what kind of house you live in or what kind of lawn you have. So don’t worry, you won’t have to ask Rose or anyone else what kind of house, lawn, clothes, jewelry, car, etc. is acceptable.

    Unfortunately, it’s not always easy for people who don’t have something causing them to interact to meet each other. I think if Rose had the opportunity to meet some of the “cookie cutter” people she talks about, she’d really like them, and they would become unique, interesting people to her. To me, many of the old timers in Westport seem alike on the outside, but they certainly aren’t on the inside where it counts.

    As for the entitlement aspect, it’s a bit overblown. To people like Rose, when a Westporter in a BMW runs a stop sign: they are “entitled”, when someone from NYC runs one here: they are a jerk; when a contractor in a truck runs one: they are a bully; when someone from Bridgeport runs one: they are a punk; but when an old timer runs one: they must have had a good reason or just made an honest mistake.

    There are bad eggs in every town. I’ve lived in much poorer and even some wealthier towns/neighborhoods than Westport, and the bad eggs here are much more tolerable than the bad eggs in pretty much every other place I’ve been. For me, the place with the least worst bad eggs is a good place for me because along the lines, of Lambie’s post: you can find beautiful people everywhere.

    Now, as for a comment on well-manicured lawns. In most of the places I grew up, having a nice lawn was a sign of pride in home ownership and respect for your neighbors. I’m not saying that people without well-manicured lawns in Westport don’t have the same pride and respect. I’d merely like to point out that you shouldn’t be so quick to judge others who very well may have good intentions/hearts.

    • Elisabeth Rose

      Wow, I’m almost afraid to say anything else and kind of wish I’d used a pseudonym for my comments, but I suppose this kind of dialogue is one of the good things about Westport: everyone has an opinion and puts it out there!

      First of all, I mentioned the “cookie cutter,” McMansion stuff only because it has been quite a surprise to me to see the changes, having often come here to visit my grandmother back when it was a more artsy town. I think that for the woman who inquired, coming from the Village, it will also seem a bit weird. I did not mean to imply that people who wore big expensive rings and lived in McMansions w/ perfectly manicured lawns couldn’t be wonderful people; I simply meant that in this town there seems to be more of a great need to “keep up with the Jones family” than there used to be, and that more folks seem to be like sheep than trying to be more individual.
      My comment about the lawns is partly because I know what the vast amount of chemicals poured into lawns every year does to the environment (…a whole other discussion…) and it just seems funny that everyone is so focused on them.

      Your illustration about entitlement made me laugh, because I’d say anyone who runs a stop sign or a red light is an asshole, whether rich or poor, from Westport or Bridgeport or whatever. It is careless and dangerous (my friend’s son died that way) and people should be careful!

      The entitlement I’m talking about is not restricted to Westport: it is that attitude of letting doors slam in people’s faces, acting better than others by acting superior, etc. But yes, you can find that all over. And sure, there are “bad eggs” and “good eggs” everywhere. I would just say that there are some things that are not so great.

      But Westport has tons going for it. If I didn’t like it at all, I would have moved years ago…!

      • “First of all, I mentioned the “cookie cutter,” McMansion stuff only because it has been quite a surprise to me to see the changes, having often come here to visit my grandmother back when it was a more artsy town. I think that for the woman who inquired, coming from the Village, it will also seem a bit weird”

        Did you really think a woman from California who has been living in NYC would think it’s odd that the Westport of today doesn’t look like the Westport of 30-50 years ago? Do you really think that this woman doesn’t realize that Westport and Darien aren’t Greenwich Village?

        ” I did not mean to imply that people who wore big expensive rings and lived in McMansions w/ perfectly manicured lawns couldn’t be wonderful people”

        You sure fooled me.

        • Elisabeth Rose

          Some people who don’t know this area may not realize how much it’s changed, particularly because there are other nearby towns which still retain some of their original stores, have fewer chain stores and haven’t experienced the boom of development, w/ the sprawling McMansions, as Westport. But perhaps not being able to compare is a good thing if an “outdoor mall” doesn’t bother you. I wish I didn’t know how Westport used to be so I wouldn’t be comparing it to the days when you could go to The Remarkable Bookstore, Klein’s, or the Movie Theater…

          My observations were that there is more wealth and showing off of it than there is in other places (and less than others, obviously). In some ways it would be like living on the Upper East Side after having lived in the Village. Like the woman we are trying to help, I too came from having lived in more “artsy” places with a very different vibe. I thought this whole thing was directed towards her, no?

          By saying that there is a greater showing of wealth, I was only trying to say I didn’t like the aspect of “keeping up w/ the Jones” and the sense of entitlement, and that sometimes, if you don’t want to run in those circles, it’s hard to find people who are not like that right away. You know, I’m sure, what I’m talking about. (Or maybe not… Is that why you’re the only one who has disagreed with me in such a sarcastic way?) Of course there are people like that who are also nice. Just because I’m describing some negative qualities about people doesn’t mean there aren’t positive ones.

          For someone who is defending Westport so much, your comments back seem awfully sardonic. We were asked to give our opinions, so I gave mine. Perhaps you didn’t read the positive things I said about Westport…

          If you’re so sure of yourself and feel like you can critize other people’s comments, why don’t you use your real name when you write in?

          • Stand your ground!
            How about:
            Rosie Riviter
            Tizzy Lizzy
            Wise Liz
            Makes it much easier to deal with the riff raff. 🙂

            • I’m in total agreement with you Elisabeth. Westport in the ’50s was pretty idyllic and we used to complain about all the NY’ers that would show up for the summer. But, Westport to me was hard because of the ‘expectation’ of wealth, keeping up with Joneses and being beautiful outwardly, not just inwardly. Luckily, I wasn’t brought up to accept any entitlement and took people for who they were, not who they pretended to be. And, yes, whoever said it, I find a lot of pretentiousness in the ‘new’ Westport. I am very thankful they haven’t torn down the beautiful house I grew up in, though they have torn down every house around it. The thing that protects it is that it’s on almost 1 acre of land very close to downtown and the McMansions aren’t really encroaching yet, burt I feel sorry for people who are trying to save their nice little (as in under 4000-sq.-ft.) heritage houses and being surrounded by these monstrosities on small lots. But that’s just me and a big reason why I’ll never live there again.

            • The Dude Abides

              If you are stoned, VET, does it really matter where you are???

  37. Well,
    I would do it all over again!!! I love Westport and I love Weston!!! The schools are awesome! The whole area is awesome! I wish I could come back home and stay. Westport & Weston will always be home to me!!!
    Good luck :0)
    Cyndi Antonio Crabbe

  38. If anyone in the family would be commuting, I would recommend renting a place in Westport or your town of choicetkg for a month or so as a trial. Pretend you have no other home and see how you feel about the commute. I.e., if Metro North cancels your train home some evening, you can’t just run home to your place in the Village. You have to pretend you only have “the one home” in Westport. This worked for me before I moved here ten years ago. I’m glad I moved here but even happier that I’m no longer commuting. E.g., one of the places I worked in Manhattan was a two hour commute door to door even though the train time was only 60-70 minutes. Four hours a day can be a chunk of your life.

    The next biggest adjustment for me in moving out of the city, (besides becoming a commuter) was losing the insanely wide variety of great restaurants that deliver at almost any time of day or night in Manhattan. (working in a creative field can mean unpredictable hours…) But then, no place can compare with New York in that department so it really isn’t fair. The good thing is that our restaurant options are constantly expanding.

    You just have to know yourself and whether you’re a city mouse or a country mouse. I’m a creative country mouse and I’d recommend Westport. Even though there are not so many like Lucy & Ricky, or Rob & Laura Petrie around, there are still lots of creative people here. And the native Westporters (here for a generation or more) that I know are all fabulous. So seek them out, and just ignore any Gordon Gekkos or Stepford Wives you may encounter.

    • Elisabeth Rose

      Gelatogirl has a great idea. Rent a place if you can, for a month or a few months, and see what you think, maybe when the weather gets warmer. Westport has some great stuff going on in the summer (although obviously the shore area is more crowded…), and you can go to free outdoor concerts at the Levitt Pavilion, behind the library or several of the area outdoor crafts fairs. In the warm late spring and summer months, people are out and about, so you’d get to meet more folks. And if you get hot, you can go for a dip either at the Longshore pool or in the Sound.

  39. Also in Westport we don’t give the middle finger, we shake our cell phones at the culprit.

  40. I moved to Westport a year ago and underwent a very similar analysis as this young family…

    Long Island and NJ weren’t in the running…. So it was down to CT or Westchester. Honestly, Northern Westchester was my first choice because it is more woodsy, quiet, rural feeling… and the train from towns like Katonah to the city is still around an hour. Spend an afternoon in sleepy Katonah or Bedford and you’ll see what I mean.

    What stopped us were the taxes. For houses in our price range, the taxes were 3X that of Fairfield County. That means I’d have to buy a significantly cheaper house just to have the same monthly payment- and pay those taxes for as long as we own the home rather than paying that money towards equity for the loan term. CT became the front runner… It didn’t hurt that I grew up in northern Connecticut.

    We looked in Greenwich, New Canaan, Darien and Westport. Greenwich is an animal unto itself- not the social scene we wanted or the environment for our kids. In New Canaan you don’t get the beach, the commute is harder and there are basically no houses under $1M. Darien was a front runner and if we had found a house we loved we might have ended up there. But the selection under $1M is still slim, the beaches aren’t that great, downtown isn’t as nice, the activities for kids (while still good) seemed less than Westport, etc. And the way the trains run, though Darien is geographically closer to New York City, you only save 10 minutes at the most on the commute. One other note if you plan to commute to New York- it is far more important to live close to the station than to have a station close to New York. Your commute will be much more pleasant if you live a short walk from the Greens Farms station than if you live in northern Greenwich- a 25 minute drive to the nearest station. Due both to the parking hassle and that extra drive at the beginning and end of your day.

    Growing up in CT, I had a lot of friends from Greenwich, New Canaan and Darien- all fantastic people. However these towns do have a reputation for pretentiousness- even my friends agreed with this assessment. Most people from other areas of Connecticut consider Fairfield County more a part of New York than Connecticut- especially Greenwich. Having said that, I’d definitely consider Westport in a different category than these other towns. Sure it’s still a very wealthy town with huge houses and range rovers and audis seemingly standard issue. But compared to similar towns in Fairfield County it does have a more relaxed, welcoming, diverse and somewhat less pretentious vibe. You’re not living in Boulder or Vermont here, but compared to the other towns in Fairfield County it does come out ahead.

    We were also swayed by the beautiful beaches in town, Longshore (basically a free country club), the sailing school, Earthplace, Levitt Pavilion (and all the activities for kids), Wakeman Farm and even the ability to paddle out to the town owned Cockenoe Island for a picnic. And I don’t know your budget, and Westport certainly isn’t cheap, but your dollar does go further in Westport than in Darien and New Canaan, especially under $1M.

    One last note I can mention… Take the train from Grand Central and look out the window and watch how the view changes. Though I wouldn’t call Westport “rural” by any means, the view certainly changes when you get to town. The mill pond and Sherwood Island are a welcome sight after traveling through Stamford and Norwalk’s urban landscape and even Darien. It’s representative of Westport’s public access to the Sound, something you just don’t get in other towns.

  41. Michael McGovern

    I have no basis of comparison vs. Darien but I have found Westport to be an extraordinarily generous community, where people give passionately their time, skills, energy and yes, money, to a wide variety of worthy causes. In my opinion, it is our “secret sauce”.

  42. Dear Would-be Westport Family,

    Growing up in the eastern part of Connecticut, I do remember those in my hometown who thought Fairfield County was most likely located somewhere in Manhattan. No surprise then that I moved here in the mid-1970s to be closer to the City. So I’ve been here a while. New Yorkers tend to think of us as “Green Acres,” but really it’s not as rural as all that!

    You’ve read about our schools, the cultural benefits, Longshore, Wakeman, Compo Beach, and (despite the feisty nature of some of our bloggers) the caring nature of those who live and work here, so here is something a bit different: a short piece written not long after we moved “north” from the beach. It’s about the particular little corner of Westport where I live now. Perhaps you’ll find it helpful.

    Watch the river otter frolic in the pond, the turtles sunning, and listen for the call of the kingfisher as he swoops down to catch a late afternoon fish. And “Daisy” and “Donald” Duck (as the neighbors told us they have been called for years) will proudly show off their baby ducks — they have three this year. It is not unusual to see a great heron perched in the highest reaches of one of the maples above the small stream and there is a surprising parade of other interesting wildlife—turkeys, a fox, mama deer and her fawn, and a glorious array of dragonflies, hummingbirds, cardinals, and more.

    We worried that with all the water that the property would be inundated with mosquitoes, but the lullaby of the frogs is happily the death knell for bugs—and evening swims in the summer under the stars are a splash of heaven on earth. The dragonflies are also prodigious “skeeter eaters” and they love the scented lavender that grows by the pool.

    One can see why Morehouse Coley sited his house as he did back in the early 1800s: It wasn’t just the ample water sources, or the fact that this land lies west of the great glacial boulders that dominate the nature preserve across the road. In the lee of Charcoal Hill, a nasty Nor’easter is barely a breeze here. It is a wondrous spot to make a home, as Mr. Coley thought, too, so long ago.

  43. There are many “wondrous spots” to make a home here. Perhaps you will decide to find one, and make it your own.

  44. Dan, you’re our own renowned hero
    A masterful conscience for 0688zero.
    So, gosh, thanks for that praise!
    I’ll now lounge on my chaise,
    and with this lyrical best —
    On my laurels I rest.

  45. Late Night Rita

    Stay put in Greenwich Village. Value of your home is increasing faster than it is here and do you really want to be a Stepford Mama????????????

  46. I’m a native. I have seen the changes and mostly I embrace them. Westport is an interesting place. If you’re in the art world here, you’re at the pinnacle. If you’re into social status.. you can climb if you want or hang with the locals. You can also be a loner here.. . bottom line, no matter what you’re into, it’s here. If you come here.. and feel like no one asking you over for dinner….call me. It’s true people move here when they’re at the top of their game.. but it gets lonely at the top, too. I can help you find a place too. 🙂

  47. People who live in and complain about Westport would likely do so wherever they lived.

    I have only been here for 40 years so I will defer to those who say that it is not the same as it was in 1950’s, but change is inevitable and, frankly, I think Westport has changed rather gracefully. Granted, I would like to see downtown buzzing more in the evening, and I think we are on the verge of witnessing such. Sure there are a lot more big houses than there used to be, but in comparison to other towns of a similar ilk in the county, we probably have a better share of smaller, more reasonably-sized homes. And like everywhere, some people are charmers…others are losers. But, overall, I like Westporters.

    Our girls got a great education, made friends they still stay in touch with, took part in the many forms of recreation available and still consider it home, even though only one has had the chance to move back…so far.

    Just recently while on one of our many walks around town, my wife commented “I really like it here” to which I heartily agreed. Maybe I will feel differently if i stay here another 20 years. I sure hope I get the chance.

    • Westport changed for the better and this has always been and will continue to be a refuge from the faster paced metropoli as well as a Mecca for the creative and accomplished, food and beach lovers. The more involved you are in the community the more you’ll love it.

  48. go for it. get the house in westport, the condo at okemo or stratton. join cedar point or shorehaven or rolling hills. your husband can ride the 6:07 bar car if he’s lucky.

  49. Westport..big houses with no furniture.

    • LOL

      In some cases, I find it both funny and sad that there are huge houses and lawns with no kids at living there… I wish all the kids who need homes could fill those places!

  50. Look at the facts, the only town that has a positive growth in population is Fairfield and I believe Darien. Westport is old news, it is struggling to keep up with the surge of Fairfield and Darien and that’s that. Tough for you guys to accept obviously.

  51. I want to meet some of you people!! Dan, should we form a fan club, a walking club, a pizza night.. something? 🙂

  52. I am a native New Yorker. Born and bred. Even stayed for college and grad school.

    About a year ago, I realized NYC was too expensive for me anymore (and I am in finance and make a very good living). And I am not talking about Manhattan, I got priced out of there long ago. Here’s some news: Brooklyn–the parts most people on this board would consider living in (slope, the hills, Carroll gardens, even fort Greene and parts of billyburg) can be as expensive as Westport, Darien, and New Canaan. When my wife ( who also works in finance and makes a very good living) realized we could sell our brownstone and for about half the sale price move into a really,really nice house in a top-suburb in Connecticut, we were shocked.

    Add in that the private schools (my daughter was in a very prestigious one) are inordinately expensive and exceptionally competitive (NYC private schools are averaging about a suicide a year), we thought we would swap for the highly rated schools up here.

    Our choices were New Canaan and Westport. Similar to cool woman. We rented a house in New Canaan for two reasons: we like modern houses ( (you cant find Breuers in westport) and someone honked me in downtown Westport. I had had enough of that in Brooklyn. It was a stupid call. One we should have researched more thoroughly.

    My daughter, a middle schooler, complains about the lack of diversity and anti-semitism at her school. She gets teased for being Jewish a lot, despite being blonde, blue-eyed, the fact her mom’s family is as WASPY as you can get (they came over pre-mayflower and we are totally non-religious (At the risk of sounding Woody Allenish i think the persons comment about westport = upper west side is a veiled reference to there are Jews in Westport).

    We considered moving back to the city. A friend from Westport reached out. Invited us to events at the school. Showed us around. Introduced our daughter to some kids. We like it a lot. We are buying a place in Westport

    I cant comment on the schools and I am sure that Westport, like everyplace, has its issues. But compared to Darien and New Canaan it is positively diverse and progressive. Guessing that if cool woman lives in Greenwich Village, where I grew up, she probably shares those views. I would also guess Westport would be the easier transition.

    • for a cool realtor. There’s a reason why Westport has a large Jewish population and it’s a great story. When I take you around showing your houses, I’ll tell you the story. 🙂