Category Archives: Westport life

What Do You Love About Westport?

Posted on September 17, 2026 | 6 comments

Cub Scout leader James Delorey writes:

At this year’s Soundview Stroll, Westport Cub Scout Pack 39 asked strollers: “What do you love about Westport?”

If a stroller took a moment to talk with a Cub Scout or Scouter, we asked them to help us discover the places that make Westport special.

We brought them over to a huge map, from the town’s Engineering Department. It includes every road, street, property lot, park, school and geographic feature in town.

Offering 6 different colored markers, we asked people to share: Green for your favorite place to explore nature. Blue for your favorite place to play. Yellow for your favorite place to eat. Purple for a favorite place to walk, bike, or hike. Orange for a place to have fun with your friends. And draw a red heart over “a place that makes you proud of Westport.”

Cub Scouts and strollers at the Soundview Stroll, with their map.

Soundview Strollers of all ages took a moment to orient themselves on the map. In this age of Waze and GPS navigation, we learned that there are many young Westporters who have never looked at a paper map of their town.

Then there were directionally gifted people who thrilled at their fluency with maps, and the chance to help the lost find their way to their favorite places.

Our map came alive with color – dots and red hearts. Runners and bicyclists drew long purple lines for their regular routes. Students drew hearts over their pre-schools and elementary schools, and orange and blue dots over the playgrounds where they play and have fun with their friends.

The Cub Scout map.

Dots for “favorite place” to eat were hungrily drawn for Old Mill Grocery, Bartaco, Casa Me and the Black Duck (one of the most fun spots to find on the map – tracing the Saugatuck River until you’re just under “Interstate 95”).

Longshore, Old Mill Beach (with dots and hearts going all the way out to the sandbar!), Sherwood Island State Park and Burying Hill Beach – Westporters love to get outside.

Intrepid explorers put green dots on the Caryl & Edna Haskins Preserve and the Children’s Natural Playground at Schine Preserve – a couple of Westport’s hidden gems (great places to explore nature).

On our map, Compo Beach is chaotic with color. Multiple blue dots – favorite place to play – were turned into a smiley face by one clever contributor. Red hearts are all over the place (“A place that makes you proud of Westport”).

The Westport Rotary Club’s lobster — aka Rick Benson — chose Compo Beach as his favorite spot, presumably for LobsterFest. The annual event — a favorite of many residents — takes place Saturday.

Our Soundview Stroll map station was really a bit of intelligence gathering. What lights up people’s faces?

Kids love thinking about the places they play, explore nature, and have fun with their friends. Parents loved seeing the places their kids chose, and how they talked about them. The whole exercise was really about starting a conversation.

And we were listening!

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Tomorrow (Friday, September 18) is “Scouting Day in Westport.” Cub Scouts Pack 39 invites all boys and girls from kindergarten to 5th grade (along with parents and siblings) to join us at Compo’s South Beach (the far end), starting at 5 p.m.

Meet new friends, make s’mores, enjoy a campfire, hunt for crabs.

And, if we’re lucky take in a well-earned sunset!

We’ll try to answer any questions you have about Scouting in Westport. But we want to hear about what you’ve discovered too.

Cub Scout Pack 39 makes s’mores at Compo, last year.

We’ll have our giant town map and our markers. Let’s share what we love about Westport, and the wider world.

Cub Scouts explore nature, play, eat, walk, bike, hike, and have fun with friends. We hope you’ll join us.

(Westport Cub Scout Pack 39 is celebrating its 75th year of Scouting. We welcome all boys and girls, kindergarten through 5th grade. To learn more, click here.

(“06880” regularly covers youth activities in Westport — and all the places mentioned here. If you share our love for this town — and this blog — please click here to support our work. Thank you!)

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Posted in Beach, Children, Environment, Longshore, Restaurants, Westport life

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Help Needed For Family’s Lost Home

Posted on September 16, 2026 | 5 comments

Three days after flood waters receded, many residents are dealing with the aftermath: flooded basements and businesses. Ruined cars. Insurance claims.

One Westport family needs a place to live, and start over.

 A GoFundMe page says: 

If you know Lindsay, you know her as the mom every kid wishes was theirs, the one who is first to say yes to a carpool, and whose house is always open for an impromptu get-together.

Most of all, Lindsay is the mom who always puts her two sons, Myles (13) and Charlie (11), first, no matter what.

Today, after Westport’s worst flood in over 200 years, Lindsay and her boys are facing an unimaginable and catastrophic loss. In the last 24 hours, the home that had become a source of comfort and stability for their family became unlivable, their contents and keepsakes were destroyed, and they also lost their car. After everything this family has already been through, this disaster has turned their world upside down once again.

Myles and Charlie, in 8th and 6th grade at Bedford Middle School, are deeply loved in this community, and so is their mom. So many people know how much this home meant to them as a safe place to heal and rebuild, which makes this loss even more heartbreaking.

Myles, Charlie and Lindsay.

This fundraiser will help Lindsay, Myles, and Charlie get through the aftermath of the flood by covering immediate needs and expenses as they figure out next steps.

Right now, they need the support of the community around them as they work to get back on their feet and try to regain a sense of normalcy. If you are able to give, please consider helping Lindsay and her boys through this devastating time.

Every donation, no matter the size, and every share of this fundraiser will help remind them that they are not facing this alone. Westport, we know how to do this. Please come together with compassion, love, and support for Lindsay, Myles, and Charlie.

As of this morning, nearly $50,000 had been raised. The goal is $75,000. Click here to contribute. 

(Hat tip: Ann Craig)

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Posted in Weather, Westport life

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Division Of Labor

Posted on September 7, 2026 | 6 comments

To many Westporters, Labor Day is a nice holiday.

We can grill, go to the beach, enjoy a relaxing Monday.

But those are perks many of us already enjoy.

Most residents here are not “labor.”

We’re management. Business owners.  CEOs, COOs, CFOs, CTOs, CIOs.

We’re entrepreneurs. Consultants. Freelancers. Bloggers.

We work hard. Many of us put in far more than 40 hours a week. Many of us work on weekends (and holidays).

For some Westporters, this is a day at the office.

Yet still, our time is largely our own.

We don’t have a set schedule. We don’t “clock in,” or fill out time sheets.

Importantly, we’re not limited to 2 weeks’ vacation a year (plus holidays).

If we want to spend an afternoon at a charity golf tournament, leave on Friday for our kid’s soccer tournament, or take a morning yoga class at the Y, we do it.

Like many Americans, we have family responsibilities — caring for an elderly parent, picking up a sick child at school, taking the dog to the vet — along with our own eye exams, root canals and therapist appointments.

It’s not easy. Balancing all the demands of modern life makes us feel like the guy in the circus spinning plates.

But for many of us, privileged enough to live in Westport or Weston, we do all those things without worrying about how it will affect our jobs.

Or whether our boss, manager or company policy will not let us do it at all.

So today — Labor Day — let’s be grateful for all the opportunities we have, in the “labor force.”

Let’s honor all those who do unpaid labor — the moms and dads who, thanks to a high-earning spouse, have the good fortune to spend time at home with their kids as they grow.

Let’s think too about all the men and women in Westport, and far beyond, for whom Labor Day is a much-needed day off.

And let’s think especially about those who are working right now, on this holiday honoring workers. From supermarkets and drug stores, to hospitals and Police, Fire and EMS departments — and so many more — we need you.

We see you.

And we thank you.

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11 Hours Left For “Day In The Life Of Westport”

Posted on September 6, 2026 | 1 comment

Submissions are pouring in for today’s “Day in the Life of Westport” project.

From midnight through 11:59 p.m. today — and only today — residents are encouraged to take, and submit, up to 3 photos, showcasing anything at all about this Sunday in our town.

People, places, events, homes, yards, sports, work, parties, streets, woods, beaches — whatever you’re doing or seeing today can be part of this community endeavor.

The first photo submitted today was this sunrise. (Photo/Elisa Martin)

They’ll become part of an online community archive and digital image library (and featured on “06880”).

Organizers also plan to create a large photographic mosaic incorporating every submission, with selected images potentially featured in a public exhibition, commemorative book, and other America 250 legacy projects celebrating Westport’s history and community spirit.

Celia Campbell-Mohn sent in this selfie, with friends.

To submit up to 3 photos, click here. Questions? Email Westportphoto2026@gmail.com.

(“A Day in the Life of Westport” is a collaboration between the Artists Collective of Westport, the League of Women Voters Westport, the David T. Langrock Foundation, and “06880.”)

Miggs Burroughs captured these flags, at Compo Beach.

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Today’s The Day: “A Day In The Life”

Posted on September 6, 2026 | Leave a comment

Get your camera ready!

Smartphones, point-and-shoots, huge ones with lenses the size of howitzers — everyone’s got at least one camera.

Today, use yours. All across town, folks will shoot images. Together, we’ll immortalize September 6 forever.

All day long, every Westporter is invited to help create a one-of-a-kind portrait of our town. We’ll do it by taking a photograph that captures one real moment from our day.

Whether it’s a sunrise at Compo Beach, breakfast with family, volunteering at a community event, working (yeah, even on a Sunday), walking the dog, cheering from the sidelines or enjoying a quiet moment at home, every image will become part of a collective portrait of Westport.

“A Day in the Life of Westport” is a collaboration between the Artists Collective of Westport, the League of Women Voters Westport, the David T. Langrock Foundation, and “06880.”

As part of Westport’s America 250 celebration, the project will document our town in its everyday rhythms, creating a lasting record of who we are as a community in this semiquincentennial year.

Inspired by the classic Life magazine photo essays documenting “A Day in the Life of America,” the project invites residents of every age to photograph one moment today. Then submit it online, with a brief caption describing what the image means to you.

Collectively, the photographs will become a real-time portrait of Westport, preserving both extraordinary moments and ordinary ones that define daily life.

Miggs Burroughs, a founding member of the Artists Collective, says, “Every individual photograph tells a story. Together, hundreds — perhaps thousands — of photographs become something entirely different: a portrait of Westport itself. The finished mosaic will reveal not only the beauty of our town, but the connections that make us a community.”

Early September will still be warm enough for a sunrise swim … (Photo/Jimmy Izzo)

LWV secretary James Delorey notes, “Westport has always been a community that shows up. Whether it’s volunteering, voting, supporting neighbors or celebrating together, people here take part. ‘A Day in the Life of Westport’ is another opportunity for everyone to help tell the story of this remarkable town.”

League member Andrea Moore adds, “Westport’s story is written by our whole community. ‘A Day in the Life’ invites everyone to share a special moment or a favorite scene from their day. Each photograph captures a part of who we are today, and creates a record that future generations will be able to look back on.”

You can photograph every aspect of community life, including all generations, neighborhoods, occupations, traditions, celebrations, acts of service, family life, recreation, arts, faith, work, and the countless moments that make Westport unique.

,,, and photographers can also capture random kids having moments of fun. (Photo/Dan Woog)

The final collection will reflect the full diversity of the community, and the many different ways people experience the same day.

Photos must be taken today — Sunday, September 6 — and submitted by midnight at dayinthelife2026.artcall.org. The submission website will accept photographs only today!

Each participant may submit up to 3 shots, accompanied by a brief caption describing the moment.

Submitted photographs will become part of an online community archive and digital image library (and featured on “06880”).

Organizers also plan to create a large photographic mosaic incorporating every submission, with selected images potentially featured in a public exhibition, commemorative book, and other America 250 legacy projects celebrating Westport’s history and community spirit.

.For more information and submission details, click here or email Westportphoto2026@gmail.com.

(“06880” is proud to partner with Westport organizations on this project — and to be your hyper-local blog. We rely on reader support. Please click here to help. Thanks for all you do for us!)

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Hey, Westport: Do We Really Even Need A Dog Park?

Posted on September 1, 2026 | 16 comments

Few topics get our readers’ tongues wagging more than dog stories.

Recent coverage of a text amendment to allow fenced-in areas at town parks drew dozens of comments. We won’t rehash them here.

But one came in after all the others. Most readers missed it.

It was not about whether a dog run is a good idea or not. Nor did it concern safety, aggressive dogs, location or anything else.

It was much more basic. Why, the writer asked, do we need a dog park of any kind? He said:

More than 90% of Westport dwelling units are single family homes. With yards. In all our time there, across 3 homes, all with dogs, not once did we take our dog to the park. We would take our Golden to the beach off season so she could jump in the waves, otherwise they were each pretty happy in their own yards and going on the occasional neighborhood walk.

Winslow Park

Then he doubled down, tossing another town amenity into the mix:

I’ll admit I also don’t understand the draw of the community garden. Each of our 3 homes had gardens, some more successful than others based on the quality of the fencing.

I live on the Upper West Side now so I get the allure of dog parks and community gardens where none of us have yards, but in the 06880 where 90%+ can do this all at home, what’s the need for dedicated public space?

Inadvertently, he answered his own question. A dog park and garden are important for basset hounds and tomatoes, sure.

But they are also about people. About society. About — and the word is right there, in the name of the garden — “community.”

Gardening can be a satisfying, solitary endeavor. But the gardeners formed a real community at Long Lots.

They educated and learned from each other. They admired each other’s plots. They shared the “fruits” of their labors (and vegetables and flowers), socializing together and watching birds and sunsets. They cheered each other’s milestones, and supported each other through personal struggles.

Westport Community Garden (Photo/Lou Weinberg)

Similarly, Winslow Park is a place where dog owners and dogs can gather together.

Humans and canines need companionship (and not just of their own kind — dogs meet other people, and vice versa).

As with the community garden, friendships form across generations. And if you want to be alone — but not feel alone — there’s a place for you.

Some people think a downside of suburbia is that people keep to themselves too much, in their own homes and yards. Community gardens and parks are antidotes to that.

But those are not the only spaces we gather, even if we don’t have to.

Many Westporters have backyard pools. All of us have access to Long Island Sound. Yet we swim at the YMCA and Longshore — sharing lanes and locker rooms.

Aquafit class, at the Westport Weston Family YMCA.

We exercise our bodies, of course. But we also exercise our social muscles.

We can all read or study alone. So why do it at the Westport Library? There is comfort in being surrounded by others — even if we don’t know who they are.

It doesn’t hurt either that — although we can make our own coffee — we can also take a break in the Library Café.

Two of the most popular events “06880” sponsors are the downtown winter and Soundview Avenue summer strolls.

What propels someone to leave a warm home in December, or a backyard pool in July, to walk up and down the street?

Music and food, yes. But the real attraction is other people.

Outdoor dining: more social than eating at home.

I could go on and on. We can worship at home, but we go to a church, synagogue or mosque.

We can eat at home, but we take pride in our many restaurants. And the buzz and vibe that is different — but present — in each.

You — and hopefully the “06880” commenter — get the point.

The question is not whether we “need” a dog park or community garden.

It’s what kind of town, or people, would we be without them?

(“06880” covers every aspect of Westport life — from every angle too. If you enjoy stories like this — or any other feature on this hyper-local blog — please click here to support our work. Thanks!)

 

 

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Posted in Categories, Environment, Library, religion, Westport life, YMCA

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Wandering Through A Rite Of Passage: The Empty Nest

Posted on August 31, 2026 | 24 comments

It’s a rite of passage: Young people go off to college.

As the last one does, their parents have their own milestone: They become empty nesters.

Do they celebrate? Mourn? Do both?

“06880” culture correspondent Robin Moyer Chung is one of Westport’s newest empty nesters. She writes:

Last Thursday, I moved my youngest child to the University of Utah, roughly 11 hours door-to-door when factoring in flight delays.

To keep myself occupied, and because misery loves company, I threw myself into an unscientific research project: What is it like to be an empty nester?

Robin Moyer Chung and True Chung at the University of Utah.

Personally, I’m freaked out by the prospect of rattling around my home of 20 years by myself. I rummage through drawers, pulling out kids’ games that haven’t been opened in 12 years and plastic bags full of broken seashells with their names scrawled in black marker.

Everything hits hard now that it’s over.

Unlike so many other life transitions — graduations, birthdays, funerals — there is no ceremony or celebration, no group therapy or organization. It’s just walking into your home and realizing your family is no longer there, a sort of “The most important part of your life is over” meets “Welcome to your twilight years.”

Gail, Kate and John Coykendall at Southern Methodist University.

For a few, it’s sweet liberty. “I embrace it all,” notes one mom. “I think I’m the only one who loved it!” adds another.

For many, however, it’s heartbreaking.

One mom summed it up: “I did not realize how much grief I would feel when my son left for college. We prepare them for this day, but I don’t think moms are prepared enough.”

While seasoned “parentes relicti” assure us the flown will fly back, the biggest question is: Who will they be when they do? Will the kid alighting on the perch be the same one who left?

Well, no.

Mattias and Christina Basler at the US Military Academy.

“The hardest part for me isn’t that they left for college, but knowing the chapter with them ‘growing up’ and living full-time at home has closed,” one mom explains.

While their childhood chapter closes, a lousy chapter often opens for the parents: loneliness.

The kids are gone, along with their social infrastructure. No more seeing parents and kids at soccer games and tournaments, no more grouping with other adults to build sets for musicals, no more raising money for choir concert tours. Happily or not, you’re expunged from the public-school email lists.

Parents celebrate their kids, before prom.

Lisa Stretton started a Facebook group last year, “Westport Moms: Embracingthe Empty Nest,” as a resource for those newly initiated into the fray. “We’re not old enough for the Senior center, there’s really no place for us,” she says. Her page offers entertainment and connection — a welcome diversion from an empty home.

While it stings for almost everyone, stay-at-home moms and single parents seem to feel it more acutely.

A widower admits, “I lost my wife, then my kids went to college. Now I have to reinvent myself.”

A single mother writes of her daughter: “All those years of having her to care for, and then nothing. My purpose was gone. I had a little bit of a breakdown and wanted to die a bit.”

Lila Greifenberger and her roommate, at Indiana University.

Alison Dorfman, founder of The College & Dorm Corner, recently posted a message that went viral: “College drop-off season: when fully functioning adults start crying in completely inappropriate places.”

As for me, a single and, more or less, stay-at-home mom, I feel anxious and untethered. But writing this article has helped keep me busy and focused on something other than my kids.

Which, of course, is the point.

(Your kids may be gone. But “06880” is here for you, 24/7/365. If you appreciate stories like this — or anything else on our hyper-local blog — please click here to support our work. Thank you!)

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25 Years Later, Westport Will Remember 9/11

Posted on August 28, 2026 | 1 comment

On September 11, 2001 Westport — and the nation —  changed forever.

The 9/11 terrorists did more than kill nearly 3,000 people (including several with local ties.) They changed our culture, politics, and sense of ourselves.

On a strikingly clear day, we saw smoke from the Twin Towers. Sherwood Island State Park was readied as a staging area that, tragically, was never needed.

The iconic 9/11 photo was taken by Staples High School graduate Spencer Platt. He lived near the Twin Towers on that awful morning.

Westporters — first responders, and others who just wanted to help in any way possible — spent time in the rubble, and nearby.

Sherwood Island is now the site of Connecticut’s 9/11 memorial. Scholarships honor the memories of friends and neighbors we lost.

Sherwood Island State Park 9/11 Memorial (Photo/David Squires)

Next month, our town will remember both the lives lost, and the extraordinary acts of kindness and unity that followed, in a special way. Officials have planned 4 days of service, to neighbors and the community.

Residents, families, businesses, schools, non-profits and community organizations are invited to gather, serve and honor together.

The 4-day observance — September 8 through 11 — will recognize the courage and sacrifices of first responders, military members and public servants, while strengthening our community through service, compassion and generosity.

Among the activities:

  • A ceremony on September 8, with a call to serve throughout the week
  • Volunteering with a participating Westport non-profit
  • Donating food, supplies or funds to a non-profit
  • Performing independent acts of kindness or community service
  • Thanking first responders, veterans, healthcare professionals, teachers, and others who serve our town

A special page on the town website (click here) includes information about volunteer opportunities, donations, and other ways to get involved.

9/11 Memorial & Museum (Photo/Andrew Colabella)

There is also an “Online Tribute Wall.” Residents are invited to share:

  • A memory of September 11, 2001
  • A tribute to someone who was lost
  • A story of service or kindness
  • Recognition of a first responder, veteran, healthcare worker, teacher, volunteer or community member
  • A message of gratitude
  • A photograph and the story behind it
  • A reflection on what September 11 means to you today.

Submissions may include a name, or be posted anonymously.

View from the Sherwood Island 9/11 Memorial. (Photo/John Kantor)

After the 4 Days of Service and Remembrance, the town will publish highlights of volunteer participation, acts of service, charitable giving, and stories of remembrance.

For now, put September 8 to 11 on your calendar.

That time of year is always busy. School, and many programs, start up again. Organizations swing back in action. Everyone kicks into fall mode.

But 9/11 is special.

Whether you were here that day or not — or were alive or not yet born — it’s time to pause.

Reflect.

And then — as Americans did, a quarter century ago — take action, in whatever way you can.

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From Germany To Westport: “My Amazing Westport Summer”

Posted on August 27, 2026 | 7 comments

It’s easy to get caught up in negative Westport noise: Too much traffic! Not enough parking! We need a dogport! No, we don’t need a dogport!

It’s easy — but why?

It’s so much better — and healthier and more fun — to count our blessings.

If we can’t do it ourselves, Paula can help.

She is 11 years old, and lives in Germany. Her godparents live in Westport. Paula visited them this summer. She had such a great time — in so many ways — she decided to write about it for “06880.”

So sit down. Relax. Read Paula’s thoughtful, insightful words.

Then realize: An 11-year-old German girl nailed it.

So the next time you’re consumed with anger, outrage or any other negative emotion, about traffic or parking or a dogport – look at Westport through Paula’s eyes.

She sure opens ours.

One of my favorite things this summer was going for walks on Soundview Drive with dogs named Teo, Lola and Bobo. Walking all 3 of them (with help!) at the same time was a little bit chaotic, but it was also one of the best parts of my whole trip.

The view is beautiful, and I loved looking out at the water while the dogs pulled me in 3 different directions. But it allowed me to met a lot of Westport people.

Paula walks down Soundview Drive, after the rain.

I also got to swim in the ocean, which is something I do not get to do very often in Germany. The water was a little cold at first, but once I got used to it, it was so much fun. I jumped over the waves and floated on my back and looked up at the sky.

Paula, doing one thing that every Westport kid does.

This summer I made friends with 3 girls almost the same age who live close by. It is good to have friends my own age around. I hope we can stay in touch and play together again next time I come back.

Something really special happened this summer: the local Westport police made me an honorary Junior Officer! They gave me a little badge, and I felt so proud. The officers were so kind and let me ask them all kinds of questions about their job. I will keep my Junior Officer badge as a memory of my summer in Westport.

Paula and Westport Police Officer Brian Quick.

I went to golf camp for a few days, and even though I am not the best golfer yet, it was really fun to learn. My swing definitely needs some more practice, but the counselors were patient and nice, and I got a little better every single day.

The birds right on Soundview were very cool to watch. Catching fish right out of the water is really special, and I loved watching them fly around and fight for the oysters. I had never seen anything like it before, and it made me appreciate how much wildlife there is around Westport.

Checking out the tidal gates at Sherwood Pond. I thought it was fascinating to see how the water moves in and out and how the gates work. It felt like a fun little science lesson mixed with an outdoor adventure.

One of the most magical evenings of the summer was when we drove our camper right up next to Compo Beach. We climbed up into the roof tent and ate pizza while watching the most amazing sunset over the water. The sky turned all these incredible colors, and it felt like the perfect way to end a day in Westport.

Camping at Compo.

Westport also has some amazing restaurants, and I got to try a lot of them this summer. I ate at Casa Me, and the food there was so good. I also went to the Lobster Shack, and it turned out to be delicious too. I also loved going to Little Barn, and Romanacci (and OMG) where we had pizza and it became my favorite spot. Of course, the bagels from PopUp Bagels were amazing to have on Sunday mornings. It made it easier being away from the amazing pretzels we have back at home.

Paula, a bagel and a schmear.

Even though all of these adventures were amazing, my favorite part of the summer was spending time with my godparents. We talked, we played card games, we laughed, we cooked together, and they made me feel so at home even though I live so far away.

My godparents also have 3 children, who are all in their 20s now, so they are much older than me, but that never stopped us from having so much fun together. They always joined in and played with me too, and it never felt like there was any age difference at all.

Every time I visit, it feels like coming back to a whole second family, and that is such a special feeling. They all took me on these adventures and made every single day feel special. I already look forward to coming back and seeing everyone again.

I had a chance to meet so many friendly people who were always kind, curious and welcoming to me in Westport, thank you for an unforgettable summer.

I already cannot wait to come back next year!

Until then, auf Wiedersehen, and see you soon!
Paula

(Hat tip: Sunil Hirani)

See you soon! (All photos/Georg Scholz)

(If it happens in Westport — or it involves anyone in town — you’ll read about it on “06880.” We rely on reader support to do it all. Please click here to support our work. Thank you!)

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Posted in Beach, Children, Restaurants, Westport life

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Turn Turn Turn: The Seasons Of Westport Real Estate

Posted on August 12, 2026 | 24 comments

Ecclesiastes (and Pete Seeger) weare right: To everything there is a season.

A time to be born. A time to die. A time to plant. A time to reap.

A time to move to Westport. A time to move away.

And a time to move back again.

David Loffredo lived here as a child. He went to the Nature Center pre-school, Riverview kindergarten and 3 elementary schools.

He was a Westport YMCA Water Rat, and caught the final out in the 1976 Little League Cap League championship game. He rode the Minnybus everywhere, and saw “Star Wars” at the Fine Arts Theater.

A remnant of David Loffredo’s Westport youth.

He returned as an adult, with a wife and toddler. Over 2 stints totaling 27 years, the family grew and thrived. He works in private equity. His wife — an obstetrician/gynecologist — is at Columbia University.

A couple of years ago, the Loffredos relocated New York’s Upper West Side. But David remains connected to Westport, through “06880.”

His journey is not unique. In fact it mirrors the arcs of many lives. I’ve often thought about families’ movements in and out of town — what brings them here, and what pushes (or pulls) them away.

But the other day, David articulated it far better than I could. He describes the various seasons of Westport life this way:

A family moves here. (“It’s the rare childless couple who moves before kids,” he notes. “We came with a 3 year old, then added 2 more.”)

The family “spends 20+ years doing all the 06880 stuff. The kids grow up, go to college, hopefully don’t move home, and ideally move to New York so you can still see them.” All 3 of theirs did.

The parents “suddenly feel old, disconnected from long time friends who either retire somewhere or fade away because the kids as glue are gone.” With their children not planning to return for at least a decade — if at all — the parents sell. David says, “I exchanged my property tax bill for an entertainment budget.”

With kids gone, empty nesters often look for a smaller place. There are many in New York City. (Photo/Dave Matlow)

With everyone in New York — David’s family is scattered across 4 apartments — there is time and space for “family dinners, concerts, plays, movies, etc. This makes all that parenting worth it.”

As time passes, “kids become adults.” They exchange roommates for “partners.” That’s where David and his wife are now, with 1 child.

As the young couple matures, “they get a French bulldog. Eventually they create a human (one of the only free activities in New York). As that human grows, they realize how intimidating it is to raise a kid in the city.”

The new family moves back to Westport “to recreate their upbringing, because how do you top it?” Hopefully, David adds, “they don’t have to commute full-time like their parent(s) most likely did.”

Meanwhile, their parents — former Westporters — “realize how much fun it is to be around their new grandchild.” So they  ditch Manhattan and retake Westport — either in “a fancy condo” or less expensive rental apartment.

Residences like The Mill attract former residents back to Westport.

David and his wife are partway through the process. But they’ve seen friends go all the way through it. He’s sure they’ll eventually do the same.

Of course, this is just one scenario. It’s not for everyone. Everyone’s life, lifestyle and life circumstances vary.

But to everything there is a season.

A time to kill. A time to heal.

A time to laugh. A time to weep.

A time to cash out, and a time to buy or rent again — keeping the Westport real estate market turning.

(“06880” regularly covers Westport real estate, Westport life — and the lives of people who live here. If you enjoy stories like this, please click here to support our work. Thank you!)

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