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!)
Empty Nesters Do Not Sell Your Westport Home.
As a Y’s Men, we have seen it too often…a Westport couple sells their “empty nester” Westport home and move across the country to be closer to their children and grandchildren. Their family are too busy with jobs, school, sports, etc. to spend time with them. The Westport couple misses Westport and their friends, so they move back. The problem is that they sold their home for under a million dollars and now it cost over a million for a Westport condo. A better plan is to rent your Westport home and use the income to rent a home near the family. That way all options are open to you and your family. Including giving your Westport home to your family when they want to move back. Turn, Turn, Turn
Agree.
I would not come back to Westport under any circumstances. My time in Westport was from 1947 to 1993. I have heard from people I knew in the late 1950s who told me the town has been fading for decades. I remember Dan had a post a while ago whereby there were 60 “For Sale “ and “ For Rent” signs on the Post Road. That’s not just a vacancy issue , that’s an outright collapse! Westport’s heyday is long gone. Those who were around 60 years ago know exactly what I’m talking about.
Jack, there is way too much here to answer in a brief reply. I’ll just say: I think you are 10,000% wrong. Westport is far from fading. It’s vibrant, exciting, alive and fun.
It’s not the Westport you lived in. Nor should it be. Towns change. They evolve. They grow.
Sure, your bowling alley, mini-golf and driving range are gone. Those — and the movie theaters — are real losses.
We’ve added so much, though. The Levitt Pavilion. As astonishingly upgraded and very cool library; upgrades too to the YMCA, Compo Beach and Longshore. A very interesting restaurant scene (with outdoor dining that is a very fun scene). The Artists Collective of Westport and Museum of Contemporary Art are both thriving. Earthplace, Wakeman Town Farm and Sustainable Westport offer programs and education for a variety of ages and interests. Even the VFW — formerly a small, overlooked and underfunded club — now is filled with jazz, rock bands, comedy, and an always-welcoming community spirit.
We are more diverse in terms of race and (especially) geographic background than in the past. (We are less diverse socio-economically, which is a loss).
We have a fantastic entrepreneurial culture, exemplified by Start-Up Westport. Men and women are working from home; they’re around during the day, not commuting, and are able to add to civic life.
The many young families that have moved here love this community. They are adding energy and excitement to it. There are also more apartments, which draw young singles and keep older empty nesters here.
There are many ways to describe Westport. “Fading” is not one of them. It’s fine to remember the past fondly. But the past is no place to live. The Westport of today is as exciting as the one you remember. Some of it’s the same; some is different. I’m sorry you can’t embrace it for what it is.
Dan,
There are pessimists and there are optimists. No one remembers the pessimists but no one will ever forget you. Many of us “old Westporters” remember you fondly and you just keep getting better. I’m proud to consider you a good friend.
Dan, I agree with you 10,000%
Jack – I don’t know you but from reading your negative comments over the years I think we are lucky you are not here.
For the rest of us who love our little town- we have been here 29 years – it is a hard act to follow, so snipe away from whichever part of the country you now reside in but, if you have nothing nice to say then why bother…
Dan, 60” For Sale” or “ For Rent “ signs on one street really says a lot about a small town of 28,000. I feel sorry for people who have businesses in Westport who don’t own the property! Also, we pay $30,000 per second in Interest on our debt in the United States. A 1929 financial collapse is coming soon.
Jack,
Won’t happen. At least before the midterms.
Westport’s certainly not the cheapest place in the US to retire, but there’s something to be said about not worrying too much about brush fires, landslides, earthquakes, biblical floods, crippling drought, tornadoes and anything more violent than the occasional hurricane leftover. Keep your house in the family, your great-grandchildren will be thankful to grow up in the lush tropical palm-tree covered Westport paradise!
👍🌴🌴🌴🌴😺😎
If you look back at my comments about the new, improved library, they were very positive. I have also made other positive comments. However, I’m entitled to my opinions without receiving insults! Westport was a quieter shoreline farming community before 1958. The town changed dramatically due to the opening of the Connecticut Turnpike. I knew a fireman who lived in Westport with his family of 5 in the 1960s, and that’s not possible now. People who grew up in Westport in the 1950s through maybe the late 1980s know exactly what I’m talking about. I’m entitled to my opinions without being insulted with words like “ leave us alone” or being rudely criticized. Paying $30,000 a second in Interest on our debt is alarming, and it’s going to dramatically increase. By the time it took me write this response, we paid $210,000 dollars in Interest on the debt.
No one is asking for an economic briefing from you, what don’t you get?
JHarte,
Be Kind.
If you can’t Be Kind.
Be Careful.
THANK YOU Dan, JHarte and Adrian .
I’ll leave it at that !!!!
This ↑↑↑.
Thank you Patricia!
As a third generation Westporter it will always be home to me. I enjoy coming back to see what has changed and what hasn’t. What is clear to me is I will never reside there again when I see properties in my old neighborhood selling for over $1.5M. As far as those who move to NYC after having lived in Westport, I don’t get the appeal of moving to the city at all. To each their own though.
I thought I just read not to have personal back and forth conversation. Doesn’t seem to be what I’m reading
Linda,
Spot on!!!
I am spending way too much time trying to monitor comments. I’m thinking of shutting all comments off, permanently. Way too many people taking advantage of this privilege.
Dan, Don’t do that. I won’t comment anymore except for Friday Flashback. I’m a bit tired anyway of the constant attacks and insults. You have my word, only Fridays.
Thank you. All I ask is that people please follow the rules!
This may be one person’s experience, but I don’t see it as universal. One of the great things about Westport is that it attracts plenty of people who don’t have kids, and retains lots of people after their kids graduate from high school. That’s because we have amenities that appeal to people regardless of their family situation — beaches, restaurants, shopping, nature, and even good, high-paying jobs in finance and many other industries.
That distinguishes Westport from towns like Darien and New Canaan, true bedroom communities that offer almost nothing beyond “good” schools (which really just means socioeconomically segregated schools).
The more Westport continues to be a vibrant hub for people of all ages and family types by allowing a diverse mix of housing and encouraging economic development and infrastructure improvements, the better for everyone.