New Residents Will Change Westport. For Good?

Westport is changing.

Since the start of the pandemic, hundreds of new residents have poured into town.

Some are singles, renting apartments springing up in the past few years on the Post Road and in Saugatuck.

Some are older folks, moving to be closer to their children and grandchildren.

But most are young: men and women in their 30s and early 40s, with kids in elementary school, preschool, day care or utero.

The influx of newcomers has put Westport at an inflection point. The new arrivals will make their mark on our community. Their influence will be felt for decades to come.

It’s happened before. In the 1950s and ’60s — the post-war, baby boom years — thousands of families descended on Westport. They turned a relatively prosperous, somewhat quiet town into a more affluent, very lively one.

The men and women who came here from all parts of the country — many transferred by companies like IBM and Procter & Gamble — jumped into civic activities. They ran for office, ran PTAs, ran Little League teams, ran around making their mark on the town.

They crossed the political spectrum, and often crossed swords. All cared passionately about making this place their home.

With help from the “Connecticut Yankees” and Saugatuck residents who had been here for years they built schools, stores, a synagogue. They bought Longshore. They brought creativity, energy and passion to every project they undertook.

In 1959, a developer wanted to buy the failing Longshore Country Club, and build 180 homes on the land. In just 19 days, the town bought it as a municipal club.

Some left soon, transferred by their company to somewhere else in America. Some stayed. A few are still here.

The newcomers of the 2020s are the same age as those who preceded them, all those years ago. They come now for a different reason: he pandemic. This time, nearly all are from Manhattan and Brooklym.

But they come with the same hopes and dreams my parents had. They want space. They want opportunities for their kids. They want a community, not just a town.

And they want to get involved, to make those dreams come true.

I am excited and energized by this wave of new Westporters. They have chosen this place for the right reasons — even if they can’t always put those reasons into words.

“It feels different than other towns,” they say over and over. “I don’t know — there’s just something about it …”

They appreciate the schools. They admire the beach. They discover the Library, the Levitt, the Playhouse. They explore the nooks and crannies that those of us who have lived here for years take for granted.

Part of the Children’s Playground at the Leonard Schine Preserve — one more often-overlooked jewel in Westport’s crown.

They want to know our history. They want to know how we got to be who and what we are. And they want to take what is here, and make it even better.

There will be battles over what that means, for sure. The Westport that the Connecticut Yankees and tight-knit Saugatuck neighbors loved — in their own, different ways — at times clashed with the changes the newcomers brought.

It will be the same in the years ahead. Our new neighbors look with fresh eyes at everything from downtown and Compo to the way we run meetings, and how we trim trees.

Westport will change. It’s inevitable. It always has, and it always should.

I won’t agree with all the changes. No one ever does.

But hey, this is not “my” town. It’s “our” town.

The next generation is ready to lead. The fathers work from home, at least part of the week; they spend more time in the community than my parents’ and peers did.

Mothers have always been the backbone of our volunteers. They were always intelligent leaders; today’s moms bring the added experience of years in the professional workplace.

I know I have described yesterday and today in broad, simplistic terms. Many other factors will determine the future of Westport — who moves into all the new apartments, for example, and the social and political trends whipsawing our entire nation.

But the bottom line is clear (to me, anyway): A new generation is here. They came for a community, and they’re eager to get involved in it. They’re making their mark already — and will continue to do so — in many important ways.

The future is not in good hands.

It’s in great ones.

Past generations had the Ice Cream Parlor. The current one has Saugatuck Sweets. Memories are made at both places.

(Newcomers and old-timers — and everyone else — are invited to support “06880.” Please click here to contribute.) 

37 responses to “New Residents Will Change Westport. For Good?

  1. Toni Boucher

    Wonderful post Dan

  2. Jack Backiel

    One thing Westport doesn’t have anymore is abundant, local recreation. There was a bowling lanes, a pool room, two golf driving ranges, baseball batting cages, trampolines, a downtown movie theater, three miniature golf courses that were jammed every night. Date night was going out to play miniature golf. Later came Arnie’s Place with games for the kids. Westport residents didn’t have to leave town to have a good time.

  3. Stephanie Bass

    Beautifully done Dan.

    Now where is that playground? My grandkids in Weston (I got lucky and son-in-law from Brooklyn: changes in population in Weston also changing) (my back stories always long and need more . then , ) so they would live to climb that slide.

  4. David Browne

    Beautiful! Welcome newbies!!

  5. Lauri Weiser

    Great article, Dan! I’m excited for this new wave of people to our wonderful community.
    I would like to invite ALL new women to become part of the Westport Woman’s Club – a philanthropic (and fun) institution in our town for the past 115 years! I am the new Membership Chair at the WWC and am happy to answer all questions and welcome all to the Club… Feel free to reach me at the email below.

  6. You have given an excellent perspective here.

    The one thing I would add is that I imagine Westport is far more affluent and that the price of housing is far less affordable than when we were growing up—and that, as a consequence, the town is far less diverse economically than during our baby-boomer days.

    I would be curious to see what the median house price in Westport was in 1963—the year my family moved in—and what the median income was in the NYC metro area at that time. My guess would be that the gap between the two is much larger now.

    I do know that the price my parents paid for our house in 1963 (which was in move-in condition being only 7 years old) was the equivalent of roughly $315,000 in today’s dollars. It was an 1800-1900 sq ft 3BR, 2Bth ranch house on just over an acre.

    Wishing all the best to all the newcomers and hope you and your families experience the same kind of happiness that Dan’s family and mine did.

    • Fred, I can tell you some properties we bought/sold and the prices. 1) 1910, 4.2 acres on Old Road for $600 dollars. 2) In 1917, seven acres on the Post Rd. for one dollar down and a $5,000 dollar ten year mortgage at 5% Interest. 3) Around 1964, a cape on 1 acre on North Maple Avenue for $24,000. 4) In 1961, 114 So. Morningside Drive built for $45,000 without the price of the land included in this price. I have the original paperwork for the 1910 and 1917 purchases, which my son has framed, in his office, but the other two are from my memory. I hope that helps? Prices soared after the Connecticut Turnpike was built around 1958.

    • Carl Addison Swanson, '66

      Fred: My father bought our house off Cross Highway for 48K in 1952, the houses on my current street, all split levels, were going for 32K in 1962 with the Marty Greenberg project. All but 3 of the 12 homes still stand, the rest tear downs. Value: 1 million.

  7. Thank you for this post. It does put into words some of what I have been feeling as a newcomer to Westport. We have been here one year as of next week and loving this beautiful community.

  8. Well said.

  9. Excellent essay. It highlights many of the interesting aspects we are discovering about this community, and it is a community, in part, because of your blog.

  10. Larry Weisman

    The salient point of this excellent piece is that’s change is inevitable and that we must keep that in mind as we plan for the future. It is our responsibility to elect to boards and commissions people who are prepared to respond to changing circumstances and to recognize the needs and aspirations of the new additions to our community whom Dan has so deftly identified at the same time as we provide for the elderly among us and for those whose financial wherewithal is less than others.
    The tip of the spear is often the P&Z which is responsible for the Plan of Conservation and Development which charts a path for the decade following its adoption. That’s why the Coalition for Westport has been emphasizing the need for new, creative approaches to land use regulation, many of which, I am pleased to say, have been implemented by the current P&Z.
    But there is another lesson in what Dan has to say, which is that because new arrivals bring new energy and new ideas, it is incumbent upon us to widen the net and broaden the scope of our welcome to new residents of varied socio-economic backgrounds by continuing to emphasize affordable housing, not because we have to but because it is the right thing to do for Westport.

  11. Jack J Whittle

    “Westport will change. It’s inevitable. It always has, and it always should.

    I won’t agree with all the changes. No one ever does.

    But hey, this is not “my” town. It’s “our” town.”

    Truth – well put Dan.

  12. Jack Backiel

    I’d like to make one more comment. Can a Westport fire fighter, with a wife and four children, own a house in Westport, and live in Westport? They could in the 1960s!


    Exuberance is exciting until the tax bill arrives

  14. Don Willmott

    In those vibrant post-war years, thousands of moms, including mine, arrived in Westport and quickly got busy getting amazing things done all around town, in part because relatively few of them were in the workplace. The percentage of working women has jumped from 38% to 73% in the past 60 years, according to a very quick bit of research. Do today’s moms have the time that my mom had to help make Westport special?

    • Westport is unique in that we have a 100% women-led Board of Selectpersons (Tooker, More, and Savin). The majority of our elected Boards are chaired by women, including the Board of Education (Goldstein), the Board of Finance (Gordon), and Parking and Zoning (Dobin). Further, women hold the majority of seats on many of our most crucial boards, including the Board of Education. So, in answer to your question, women indeed continue to do the vital work that makes our town special.

  15. Well said, Dan.

  16. Carl Addison Swanson, '66

    It is a bustling suburb not a town anymore. The Wonder Years of Westport’s big transformation in the late 1950’s-1960’s is long in the rear view mirror and Herb Baldwin, who did not want this town to be for the very rich, is turning in his grave.

  17. Michael Nayor

    It is heartening to witness newcomers giving Westport a shot in the arm. Yes, change is inevitable. Newbies will be a driving force but not the only one. Our own P&Z Commission understands that we can’t stand still. The times require that we anticipate what is necessary to service our residents and make this a first class community. The Coalition for Westport has been a moving force for the last ten years in recognizing these needs and advocating for enlightened change.

    Preservation is important. Nostalgia is important. Dan Woog is nostalgia personified. Yet he is an enlightened soul who is capable of putting needs and choices in perspective. Hurray to you Dan for writing an article that reflects needed maturity and wisdom on this subject.

  18. Jack Backiel

    The new Westport residents should know that this was a small town, even though the following people, at one time, lived in Westport: Marilyn Monroe, Bette Davis, Kirk Douglas, Elizabeth Taylor, Paul Newman, Robert Redford, Zsa Zsa Gabor, Erica Jong, Charles Lindbergh, George Gershwin, James Thurber, Harry Reasoner, J.D. Salinger and many, many more. Yet, at the same time these people lived in Westport, Westport firemen and policemen lived in town. Farmers, like my family, lived in town. In 1958, I went trick or treating at Elizabeth Taylor’s house and she handed out candy bars.

    • Jack, great point. Let’s not forget our other famous Westport residents; Harvey Weinstein, Martha Stewart, and Jim Nantz.

      • Carl Addison Swanson, '66

        Michael Douglas (on my Little League team in ’58) lived here with his Mom and Step-father. Kirk did not live here. Zsa Gabor married a Westport cop for about ten minutes, Thurber lived in Weston and Salinger wrote “Catcher in the Rye” in a rental house off Old Road in ’52. What many do not realize in the bravado about these famous residents, is that they lived here because nobody bothered them. Now, the ones who are left, are in Weston or upstate.

        • Jack Backiel

          Carl, Kirk Douglas took Michael to California, and Joel stayed. I’ll give you a few more though: Harry Reasoner, Mike Todd, Rod Serling, Dan Woog, Mia Farrow, Linda Blair, Jason Robards, June Havoc, Robert Ludlum, and Martha Raye. One of my relatives worked for Helen Keller, but technically, she may not have lived in Westport proper. And here’s another we’ll known name- Fiorello LaGuardia. I do think you’re correct when you point out that these people could live in Westport, blend in, and not be hassled. If anyone can add to this list, please do.

          • Carl Addison Swanson, '66

            Max Shulman, Rodney Dangerfield, Marilyn Chambers. Beg to differ Jack, but Michael was closer to his step father growing up than Kirk. I know he spent his summers here and went to Choate for high school. Still bump into him in Bermuda.

  19. Jo Ann Miller

    Westport used to be super cool with a variety of unique individuals including the celebrities Mr. Backiel mentions. We also had some economic diversity. Now? Financial folks. Yawn.

  20. Jack Backiel

    Yes, we did have a lot of economic diversity! Also, Dick, please don’t get me started on Martha Stewart! I don’t like posting negative comments.

  21. Surprised that to date there has not been a way to find how to put to work the most underutilized and underachieving piece of real estate in the town. Most communities with sophisticated and creative, talented people find a way to maximize resources and designate highest and best use to what they have. To dedicate a the most prime chunk of square footage in the town to a parking lot is consistently absurd and a huge failure of our politicians and ultimately our residents. Downtown along the river, to our great loss is the home of parked cars, not of restaurants, parks, cafes and even a small amphitheater or whatever. Huge waste. To the newcomers with energy; fix it.

  22. So happy you said history is involved. It can’t be removed like the new woke generation says it can. I’m happy people want decent lives for their children with history!

  23. Where’s my comment

  24. Jeffrey Lampert

    Hi Dan,
    Great article as you are always on the pulse of the town and whats going on and happening. We appreciate all the updates and thanks for keeping us residents in the loop!


    Wonderful article

  26. Moved to town in ’68, left in the mid 90’s. Frank Gorshin, Ashford & Simpson, F. Scott & Zelda? So many more.

  27. Christine Maraia

    Wonderful article!

  28. As postwar immigrants and newly arrived from their 1st stop in Brooklyn my father and mother bought our Long Lots Road house (little red house next to the Hunt Club, still standing) for $5500.00… they stretched and couldn’t come up with the Realtors commission so he said ‘pay me when you can’ they paid the next month and were lifelong friends. A few years later they built an addition on to the house and became great friends with the builder. Dad was driven home safely by a well-known WPD Sergeant a few times for reasons we won’t talk about. They raised 3 kids, commuted to NYC daily (Dad screamed when the monthly pass went over $50). We all had a wonderful, creative and fulfilling life in Westport… and they thought they had hit the lottery when they sold the house for almost $80k in 1970!