You can see the new Westport everywhere.
In line at new favorite spots like Sweetgreen, Cava and Momu.
At Compo and Old Mill Beaches, where families gather for early evening picnics.
And particularly at last month’s Soundview Summer Stroll. Over 3,000 Westporters jammed the beach exit road for the first-ever festival. There was food and music, plus kids’ fun like rock painting, street chalking and balloon art.
Children swarmed those activities. Everywhere I looked, I saw young parents, with young kids. And it seemed that just about every young mother was pregnant.
It was fantastic.

A small part of the large Soundview Stroll crowd. (Photo/Benji Porosoff)
Westport is at an inflection point. A new generation of residents has arrived.
We’ve seen the statistic: Westport had the greatest influx of newcomers during COVID of any town or city in Connecticut.
That’s not per capita. It’s actual numbers.
And they keep coming.
They choose Westport for the right reasons. They’re looking for a place with excellent schools, great amenities, and — equally important — a sense of community.
(Interesting factoid #1: They’re also looking for space. That’s because 99% — or so it seems — come from Manhattan or Brooklyn.)
(Interesting factoid #2: Among the attractions that realtors sell — recreation, education, restaurants, entertainment — they seldom mention the Library. When new residents walk into the building for the first time, they’re blown away by this unexpected, but spectacular, amenity.)

Everyone loves the Westport Library. (Photo/Eve Potts)
In 1956, my parents chose Westport for similar reasons. They wanted my sister and me to have good schools, open space, and beaches. (Longshore came later. So did my other sister.)
They joined a massive post-war exodus to the suburbs. I joined dozens of baby boom friends. We joined sports teams, Scouts and other organizations. We joined each other, playing up and down High Point Road every day until dark.
My mother joined a garden club, and musical groups. My father joined the RTM.
They — and so many of their friends — helped lay the foundation for what this town is today.
Westport was at an inflection point then. I’m sure the people who had lived here for years — “Connecticut Yankees,” Saugatuck tradesmen and town workers, established artists and writers — wondered what was happened to their town.
It was changing rapidly.
There was new spirit, new energy.
Also: more traffic. Higher taxes, to pay for new schools and services (and the purchase of Longshore).

The purchase of Longshore — including this tower (since torn down) near the entrance — in 1960 was a seminal moment in town. (Photo courtesy of Peter Barlow)
There must have been tension. But life went on. Westport changed, evolved.
And prospered.
As everyone at the Soundview Summer Stroll saw — or who watched the endless stream of kids marching in the Memorial Day parade, or waits in line at any place selling pizza, chicken tenders or ice cream — our town is changing again.
I love it.
The new families bring their own new spirit and energy. They make a fresh impact on every aspect of town life: our schools, stores, sports and everywhere else. There’s a buzz in restaurants and downtown we haven’t felt in years.
Some folks grumble. Traffic is worse! The new folks build big homes, and cut down too many trees! They seem entitled!
Perhaps.
But now this is their Westport too.
Long-time residents can be grumpy old folks, yelling “Stay off my lawn!” But it’s so much better to invite the new neighbors’ kids to play on it.
Older residents too can be King Canutes, trying in vain to stop the tide. How much nicer though to wander over to a new family enjoying dinner at the shore, and introduce ourselves to them.
Our town is at an inflection point. Hundreds of new, young residents are here. More come every day.
This is their Westport now.
But along with the excitement, there’s a challenge: It’s their job to make this place even better tomorrow than it is today.
So, decades from now, they can hand it off to a new generation of newcomers.

Kids are everywhere. They join groups like Scouts. They participate in the Memorial Day parade. Their parents are getting involved in town affairs. It’s a fun, exciting time. (Photo/Stephanie Tang)
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Hat’s off to you Dan Woog for your part in bringing Westport together !
Ahhhhhhhhh…..Change is Constant! Great article Dan!
great article. Be kind and tolerant to all.
Dan you’re the best. Yes yes all of the above and more our town offers it all … We moved here in 1996 🩷👍🌈 Best move for our family🌊… we are still very close friends with our initial group of friends from an organization, called “New Neighbors” … Although a lot of them have moved we are all still in touch … and they are subscribers to 06880 ✍️. With many thanks to you keeping us all in the know. ❤️
I’m so excited! And I just can’t hide it!!! I’m about to lose control and I think I like it!!!!
But one major change in many places—and especially a town such as Westport—is how much less affordable housing has become since you and I were growing up (and even since the time Debbie and I bought a home as 40+ adults roughly 30 years ago).
In 1963 my parents bought an 1800-sq-ft home on an acre in the Coleytown section for an amount that equaled roughly $330,000 in today’s dollars.
In 1995 Debbie and I bought an 1100-sq-ft home on a 1/4 acre in a fabulous location near the beach, the train, etc for an amount that equaled roughly $443,000 in today’s dollars.
It would seem that the newcomers’ children will be going to local schools where there is far less economic diversity than years ago.
My perception is that the population of Westport has been 27,414 since the first time I looked it up around 1970. What is the actual population today?
No way, Don, that pop was 27,000 in 1970…was about 22-23,000 back then and is 26,000+ today.
And, of course so many of those newcomers are returning residents (perhaps more than ever?), such as myself. Surely, this is a testament to the wonderful childhood experiences many of us had here and our confidence in the community’s ability to provide the same opportunities for our children, the next generation.
Of course, that “community” is now us, my generation; thank you Dan for the kind reminder that we now inherit and share in this collective responsibility.
I’ve liked and appreciated the tenor of both yesterday’s and today’s blogs … love our town and her changes.
But it is also appropriate to voice concern about the potentially negative impact of changes that happen too quickly, all at once, without being prepared.
Traffic IS a big problem. Cutting down mature trees to build a bigger house or a better restaurant IS disturbing.
I spent my summers at Compo Beach as a child/pre-teen in the 60s. When I moved here permanently 18 years ago, I was delighted by how much everything had remained the same. Sure, there were lots of changes, some growth, definitely a less bohemian population – but it mostly looked and felt the same.
Then about 8 or 9 years ago POW! there was an enormous shift.
Not all for the better.
Change does and should take place – incrementally. If there can’t be forethought, there needs to be mitigation.
There will always be a new, younger influx of residents here in Westport. After all, the “older, long time residents” were once new and younger! (smiling) That’s a good thing.
My point is this:
There’s room for being welcoming, accepting AND prudent.
I am part of the group of people who lived in Westport before 1950. While my families’ roots in Connecticut go back to the 1600’s on my mother’s side and the late 1700’s on my father’s side both families were back in Connecticut and specifically Westport in the early 1930’s. Both of my parents attended Staples High school….the old, old building om Riverside. The proximity to New York City was one factor but the beauty of the area and the schools were another. As an adult looking back, I think that the most attractive element was the people. My Father’s family lost everything in the financial crash of the 1930’s and never recovered financially. My mother’s family was more fortunate, but a nasty divorce left her mother as a single woman with four children.
The wealthy, well educated, exceptionally talented people did not set themselves apart or above those less fortunate. As a child I can say that Lucy Bedford Cunningham Warren would come and visit my mother volunteering at Norwalk Hospital, often with me in tow. Artist Bob Lougheed gave my Grandparents a painting before he left town in thanks for their friendship. Mrs. Roman (Gertrude) Heyn befriended my grandmother after her divorce.
There is a long and wonderful story there. You just might run into Paul Newman in one of the diners. Betty Roberts, wife of First Selectman took me under her wing and made a huge impact in my life. And let’s not forget the natural area, brooks, the beach, Ford Road and pretending the Red Coats are coming riding our bikes everywhere. I could go on and on. Roots are very important and sustain the tree, give it food and stability. The roots in Westport go back to the very beginning of our country. Good roots sustain a strong tree. Westport’s roots are strong, and I am so pleased to hear that the atmosphere in Westport hasn’t changed and continues to nurture its residents of all ages.
Well said, Dan!
My family and I are “new” as well, although we arrived just slightly pre-pandemic. Our almost-five years here have been amazing, and it’s funny to think that we are able to talk about how much has changed since WE moved here! Haha!
This is such a great blog/site, Dan, thank you for providing it. I am a happy subscriber, and if you’re reading this and you’re not a subscriber, you should be!
Dan, Thank you for your generous article (and all that you have ever written) praising the energy, creativity, compassion and extraordinary support citizens of Westport have toward the town, its storied history, its young and old, the wealthy and less wealthy, and for neighbors close at hand and those further away who have benefitted through the generational generativity of this community.
When we moved to Westport, my father just got a job in Manhattan. He got home every night at around 7 PM, tired. On weekends he played golf at the Patterson Club (before the town owned Longshore). He had no involvement in Westport.
Dan, such an excellent article to read! To know you and having spent 24 years at Oscar’s Deli your words bring back the best some of the best memories of my life!