“43 Questions To Ask” Before Moving To Westport

If you’re a Westporter, something got you here.

Maybe it was a town you once visited, and wanted to live in ever since. Maybe it was recommended by a friend. Maybe you methodically researched every place within an x-mile radius of y. Maybe you’re here because your parents lived here. Maybe even your grandparents.

The longer you’re here, though, the more you realize this town is different from every other.

And the more you realize it’s the same. Because, after all, every town is really just the sum of its shared values.

Yesterday’s New York Times “Your Money” column provided a fascinating look into that subject. In “43 Questions to Ask Before Picking a New Town,” Ron Lieber writes that a “values audit” is a good way of finding the best place to live — better, in fact, than school test scores, short commute or most house for the money.

According to the NY Times, checking out the library is a good way to learn about a town.

According to the NY Times, checking out the library is a good way to learn about a town.

Lieber’s advice is solid. Of course, he got help from experts — like former Westporter Alison Bernstein. (She runs Suburban Jungle, “guiding people to the places within commuting distance of New York City that suit them best.”)

Among the ways to scout out a new town:

Online forums. Check newspaper websites — and local versions of “06880” — to see what’s important in each town. And what are the comments like?

In-person reconnaissance. Bernstein advises parking in front of the nursery school at drop-off time to see who goes in and out: Nannies? Dads? Working moms? And how are they dressed? “If it’s chicks in yoga pants and you want that, great,” Bernstein says. “Just know what you’re getting into.”

Check out the high school to see whether students leave campus after school for team practice or to smoke cigarettes.

It's one thing to look at a school building. It's another thing entirely to see what goes on in and around it.

It’s one thing to look at a school building. It’s another thing entirely to see what goes on in and around it.

Eavesdrop on the sideline of sports games. “What dominates the conversation?” Bernstein asks. “Politics? Work? SoulCycle? Babysitters?”

Caregivers. If you’re a stay-at-home dad, will you feel at home? Will your babysitter need a car, and if so do most people have 3rd cars?

Mental health. “Are the local children garden-variety pot smokers who have a little sex and a bit of angst at a reasonable age, or is something more troubling going on?” Lieber writes, in one of my favorite Times sentences ever.

How do you find out? “Buy an hour of time” from the town’s leading child psychologist.

Summer. Is this a town-pool or a country club place? Does the town empty every summer because most people have 2nd homes?

Potential home buyers should watch a Compo sunset -- but also talk to folks on the beach.

Potential home buyers should watch a Compo sunset — but also talk to folks on the beach.

There are other suggestions too, like looking at the town library’s shelves, and writing the mayor.

I wonder what potential home-buyers will think about Westport, when they follow Lieber and Bernstein’s advice.

Will they read “06880,” and think this is a place filled with rude drivers, and where every old home is a teardown? Or will they think it’s a place that adores its beach, cherishes its beauty, and whose citizens speak passionately on every issue?

What will they think when they see the enormous variety of people dropping off their pre-schoolers? Can they tell by watching that we have a huge population of stay-at-home moms (and dads), and another huge population that rushes off to high-powered jobs?

Will they realize that many of the folks who are here in summer are not the same people who live here year-round — but many are? Will they know exactly who is grilling on South Beach on Tuesday evenings? What will they make of the many languages they will hear on the boardwalk, in Joey’s, at the playground?

Another place to learn a lot about Westport.

Another place to learn a lot about Westport.

Those are fascinating questions. There are probably as many answers as there are Westporters. Click “Comments” (and please use your real, full name.) The “06880” community would love to hear your thoughts.

So would all those other people in the Suburban Jungle, wondering if — and why — they should buy a home here.



13 responses to ““43 Questions To Ask” Before Moving To Westport

  1. Rich Stein

    Dudiligence, homework, “peeling the layers of an onion,” and reconnaissance are all thoughts that popped in my head while reading this blog today…. Observe observe observe…. Sit at the different coffee stops and or popular watering holes and ask questions of the locals… When on a vacation ask a bartender where he would eat for the true flavor of his home town and you find some gems

  2. Alison J. B. Patton

    Thanks, Dan. I appreciate the invitation to look further than test scores and ‘top ten’ reports to get to know a town. Some of Lieber’s questions are helpful. Some a little troubling (and could say more about our assumptions than about the town in question): how exactly does one know who’s a parent and who’s a nanny by watching from the parking lot? In the end, I do wonder whether the only way to really learn about a community is to become a part of it. There’s no such thing as a ‘perfect town:’ Every town has its strengths, quirts and struggles. What’s powerful is when a town becomes ‘my town,’ quirks and all. Scoping out the values and culture of a place may be a part of getting ready to move, but I suspect that moving in means choosing to love, learn from, contribute to and give back to the place you live, wherever you plant your feet.

    • GREAT thoughts, Alison. I hope your experience here so far has been a good one. Welcome to Westport!

    • Tracy Flood

      Alison- I thought for sure you’d suggest checking out a couple of houses of worship!!!!!

      • Alison J. B. Patton

        Excellent point, Tracy! Yes: Find a community of faith and explore what matters to the the folks there. How are they building community, engaged in the town, nurturing/challenging participants and making a difference? These are questions i would ask. I wonder what others look for?

  3. Mary Ann West

    One of the most glaring tip offs I notice, be it a specific town or area, not just for moving-in but long term relationship potential would be the perceived strength of the local planning & zoning requirements as evidenced by housing and building stock. Does there seem to be forethought of preservation of historical buildings. or is this an area of newer buildings or a mishmash of low end development?

    Having lived in Southern California, home to the “Valley” while driving, can you tell when you’ve entered into a new town, or is there no differentiation in character except for the change of town signs, in-between the strip malls, if even that?

    Do I want to live in or even patronize a town where any and every building can and does get built? Is there signage control etc… Are there comfortable streetscapes that I will want to see often or is this an area that is a drive-by on the way to somewhere else?

    The political wind at a local level is also as important to me, as is the quality of the schools and community involvement. Sure I can do a lot by internet searching, when traveling, I always try to pick up the local papers, they are a strong indicator of what is of interest to the area and a wealth of information within a few pages.

    Admit it, do you checkout the house listings & ads to see what houses go for there compared to here? I do… all the time.

  4. Rindy Higgins

    From my standpoint, one indicator of a healthy town is its respect for the natural environment. How does it handle its garbage/recycling/waste water, its P&Z and Conservation codes, preservation of and access to natural areas ? Westport does a good job at most of these. Its multiple parks, including its beaches, Saugatuck River and Long Island Sound access, its Wakeman Farm and Earthplace, the oft forgotten Sherwood Island State Park with its seasonal Nature Center, and provide many “no person left inside” opportunities.

  5. Nancy Hunter Wilson

    Simple stuff suits. Are kids playing outside? Do passersby greet each other with “good morning”? Do neighbours know their neighbours?
    Looking at the town library shelves is an interesting thought (to make sure “Hop on Pop” isn’t banned).

  6. Russ Brenneman

    Is this a place that welcomes and provides safe places for folks to walk and use vehicles other than cars? Is there ample and convenient public transit? Is there enough convenient parking at the train station for those who depend on trains?

  7. Nancy Hunter Wilson

    A wheelchair accessible transit system?

  8. brian faucher

    “Bernstein advises parking in front of the nursery school at drop-off time to see who goes in and out” …..sounds a little creepy to me. Just don’t do it from a windowless van, otherwise you might find out more about the town’s police force than you want to! 🙂

    • Elizabeth Thibault

      Everyone would just assume the van belonged to a contractor, since it seems that we’re in the perpetual state of a remodel somewhere!
      Can we amend the bit on being in yoga pants, because many of us now work from home a significant portion of time… and let’s be honest, there’s more to these pants than just saving on the dry cleaning!

  9. Jo Ann Davidson

    Last Sat we took the tour of the Water Treatment Plant. Like our Library, it is a State of the Art facility, and reflects Westport values. We protect our environment and get what we pay for, and it’s another reason this town is such a good place to live.
    Jo Ann Davidson