The other day, a woman I did not know made idle chatter as we left the Westport Weston Family YMCA.
“This is such a nice place,” she said. “How long have you been a member?”
“Well,” I said, “I learned to swim back in old pool!”
“There was another pool here?” she asked.
“No,” I explained. “When it was downtown.”
“The Y was downtown?!” she replied, surprised.
“For about 90 years,” I said.

The original YMCA, built in 1923 (now Anthropologie). The beautiful trees — along with the Y — are now gone.
She must be one of the new COVID arrivals, I figured.
Nope. She moved here 3 years before that. She’s been a Westporter for nearly a decade.
How could she not know the YMCA was downtown — and that there was a years-long battle to keep it from moving from the old site to its current spot?
Then, I realized: How would she know?
The controversy — to leave what is now Anthropologie; the rejection of possibilities like Baron’s South; fears about traffic on Wilton Road; demolition of the “newer” Y buildings on Church Lane, and construction of Bedford Square — pre-dated her Westport life.

Construction of Bedford Square, 2015. Patagonia (formerly Westport Bank & Trust, soon to be Compass Realty) is in the rear.
To her, the Y was “always” at Mahackeno. There is no way — other than reading an occasional “06880” reference to it it — that she would know otherwise.
Which got me thinking: What else do those of us who have lived here “a while” take for granted, but which no newcomer would ever know?
The Westport Country Playhouse is one example. New-ish arrivals may hear about it — on this blog, through a flyer in the mail, or osmosis.
But unless they are musical theater buffs, how could they have any clue of the role the Playhouse played in American entertainment history?

The original Westport Country Playhouse, before its 2002 renovation. (Photo courtesy of Bill Stanton)
Its origin in 1931, as one of the first “summer theaters” anywhere? The legendary names — from Henry and Jane Fonda, to Olivia de Havilland and James Earl Jones — who have performed there? The roles Paul Newman and Joanne Woodward played in modernizing it, in the early 2000s?
(And, to be brutally honest: How many 30-somethings know any of those names in the paragraph above — including Newman and Woodward?)
The hundreds of new folks who have flooded into town over the past few years were attracted by amenities like Longshore. Realtors proudly showed off the golf course, tennis courts, pool, Inn and restaurant. They mentioned that it’s town-owned — not private — and open to all.
Did those realtors mention the back story: That the town bought it in 1959 for $1.9 million, to keep it out of the hands of a developer? And that if those leaders had not acted quickly, 180 homes would now be there instead?

The town’s purchase of the failing Longshore Country Club kept it out of the hands of developers.
Speaking of government: I’ve spoken recently with residents who mentioned our “mayor” and “town council.”
Maybe in New Jersey, Florida or Arizona. But here in Westport, our New England heritage includes a “first selectman” (currently, “selectwoman”) and “Representative Town Meeting.”
The RTM can be a mystery — particularly when only the initials are used. What does it do? Who is on it?
A
gain: How would any newcomer know the answers? Even those motivated by a particular issue — Long Lots School, say, or bike paths — may have only a vague notion of the RTM’s role in our town.
Nor may they know they’re eligible to serve on it. (Though not until 2027 — the deadline to run in this election has passed.)
There is so much more that older/longer Westporters know, but comes as a complete surprise to those who have been here even 6, 8 or 10 years.
Like: Staples High School was originally on Riverside Avenue. (And that before it was Saugatuck Elementary School, the building was also known as Bedford Junior High, and Bedford Middle School. The “new” Staples — opened on North Avenue in 1958 — has its own intriguing, tangled stories of renovations, starting with 9 separate buildings more suited to California than Connecticut.)
Or that the “Bedford” name refers to a fabulously wealthy family, with ties to John D. Rockefeller’s Standard Oil Company. And that their generosity can still be felt in many areas around town, including — let’s complete the circle — the YMCA.
Once upon a time, newcomers would learn all this, and more — The town of Westport bought Cockenoe Island in the 1960s to prevent it from becoming a nuclear power plant! — through stories in the local newspaper.

Westport owns Cockenoe Island. The town bought it when a utility company planned to build a nuclear power plant there. Pro tip: It’s pronounced “Kuh-KEE-nee.”
Westport had a newspaper?
Not one — several. The Town Crier. Fairpress. The Minuteman. The Westport News.
In fact, the Westport News still exists. Sort of.
It’s online (behind a Hearst paywall): http://www.ctinsider.com/westport.
There’s even a print edition, which seems to be sold nowhere in town, but may be available for home delivery if you are persistent enough with their hard-to-reach customer service people.

Which reminds me: Most new residents do not know — how could they? — that “06880” began in 2009, as an outgrowth of my long-running Westport News “Woog’s World” column.
Or that I began writing for the paper when I was a Staples student, way back in the day.
Just a few years after I learned to swim, at the downtown YMCA.

The original YMCA Brophy pool. It was used for Staples swim meets, before the high school pool opened in 1981.
(Another fun fact: “06880” is a non-profit, supported by donations from readers like you. If you enjoy your new — or old — town’s hyper-local blog, please click here to contribute. Thank you!)

I spent a lot of time at the Y downtown
Dan my family moved to Westport from Brooklyn NY I. 1960 after other extended family members to join a family owned real estate development business Pace Buildwea/Carol Construction in Westport. The Wisser family remember all of those memories you mentioned and many more.
I love reading 06880 every morning.
as a 1972 graduate of Staples, having attended Coleytown Elemenrary, ColeytownJunior High I love reading about families we all grew up with and community events that we all share.
Thos particular post warms my heart.
With Gratitude
Ilise Gold, LPC
formerly Ronni Wisser
Love 06880! Brings back moving to Westport in August of 1958, Working on the Bedford Estate in high school and college summers, Miss Ruth Bedford, her love of her dogs, the Old downtown Y where my Downshifters, VSC ( Volunteer Service Club), Hi Y met weekly. Camp Mahackeno summers as a counselor in training, Vince Perry. Great memories Dan! Thank you!
Some people might not know that the building that is now Town Hall was once Bedford Elementary school. Whenever I go in there (which I don’t pay my mom’s taxes on visits from California), I ask the guy at the front if he’s subbing for Mrs Mailins (who was the school secretary in 1964 when I started there, and sat I. Roughly the same place. He walkways looks at me a little funny…
Not knowing that the Compo playground was litigated, or that Players’ Tavern existed, bespeaks a lack of curiosity. But not knowing your form of government evinces willful blindness.
One other tidbit: The Brophy Pool earned that moniker after the Brophy family, most notably brothers Joe and Jim, both Staples Swim Team captains in the 1960’s, donated family money to convert the original Y pool, from its configuration of 20 yards, to 17 yards, in order to make room for the sleek and modern Stauffer Pool which was opened to swimmers in 1978, the year I became Aquatics Director for the Y.
Wait, What? The Y is no longer downtown? Are you going to tell me the fire department has left Church Lane too?
My grandparents, who lived on Old Rd, had eight children, one being my father, and all were born in the farmhouse, Not many people can say my whole family was born in Westport. The first child born around 1906 or 1907, died when only a couple of years old, and no one knows where he’s buried.
I have to correct my previous comment. Everyone was born in Westport , but the farmhouse wasn’t built until 1910, so the only ones who were born in the farmhouse were born from 1911 to 1918.
Well…when my family moved to Westport in 1963, the Welcome Wagon presented to my mom “A HANDBOOK FOR WESTPORTERS” published by the Westport League of Women Voters.
It was inscribed at the top of the front cover “Mrs. Sidney Cantor, 23 Easton Road” and the woman who gave it to my mom also wrote her phone number on the front cover: “CA7-5229.”
There was a ton of information in it. So that was Indeed helpful back in the day.
Nice history lesson!
Thank you, thank you Dan. We all love you. When we moved here in 96 the Westport news and Minuteman news were my first connection to town. Thank you for being our continuation of being in the know …. Always keeping us up-to-date with the real news You are the best 🩷👩🎨Dorothy
Thanks to Dan for chronicling the changing face of our vital community. My family (the Remarkable Sid & Esther Kramer) arrived in Westport in 1950 from the heart of Brooklyn. I grew up at RTM meetings, in a front row seat to a local functioning democracy. I benefited from the outcomes of these many struggles. Each of the changes/developments mentioned above engendered discussion, debate and controversy. They provided lessons for a lifetime, templates for today. I’m very much in touch with my fellow 1960 Staples graduates. Each of us marvels at how lucky we were to have come of age in such a unique place.
Thanks Dan. Considering the rich history of Westport and the fact we all have an expiration date, have you ever thought of writing a book on Westport history? I assume you have a treasure trove of background material. From its beginnings as an arts colony to its marketing heritage, its unmatched contribution to the arts and entertainment, its famous residents both past and present who chose Westport for the chance to be out of the spotlight (yes, some actually like that). When we moved here we were told in no uncertain terms that the unwritten rule in Westport was NOT to be a “fan” and create a fuss over any celebrities you might come across. Say hello, wave, maybe a comment of appreciation but keep Westport a safe haven for quiet living. Can’t tell you how many times we walked past Paul Newman in jeans and a t-shirt enjoying an ice cream in town. A pleasant hello exchanged and continue with our activity. A favorite recollection as long time members of the Playhouse was sitting next to Mr. & Mrs. Newman and upon the lights dimming and the play starting, hearing the unmistakable sound of a little hard candy being unwrapped……..by Joanne Woodward! Now, anyone who isn’t a play-goer doesn’t get why that is so funny and ironic. I guess my favorite bit of history was finding out that the Wakeman Town Farm & Wakeman Field was once a Nike Ballistic Missile site with its control tower a mile away at the now observatory. A great friend of ours, who was a Westport resident for over 50 years told of breaking into the decommissioned site and playing in the missile silos! Having passed away a few years back I only wish I had suggested he write a book to capture these memories. So maybe consider it Dan. I’m sure your readers would be happy to contribute material, photos and other exhibits.
Hey Phillip!!!
I agree and would like to propose a title for the history of Westport: How about “Westport IS History!!!!”
Thanks, Phil. Much appreciated. Great memories, and insights.
I thought you were pulling my leg with the “decommissioned missile site” story. I too played in those silos, as a little kid. Hard to believe now, but true.
As for a book on Westport: that would be quite an undertaking. I’m not sure — with the 8 or so hours a day I spend on “06880” — that I have the bandwidth to do it. (In fact, I know I don’t.) But I appreciate the suggestion.
And just to complete the circle: I did write a book (400 pages!) on the history of Staples. Published in 2005, it’s called “Staples High School: 120 Years of A+ Education.” It covered everything from Horace Staples’ desire for a school in his home town, to the growth of public education in America, to the school’s innovative leadership nationally in the 1950s to ’70s, on through the construction of the “new” building. It’s out of print now, though the Westport Library has a copy, and it occasionally pops up at the Westport Book Shop.
I have a copy of all of Dan’s books and will loan them out free of charge (it’s my way of “giving back.”)
My family arrived in 1930. It was downhill from there. Somebody needs to talk to the “Y” about the sewage they’re dumping into Lee’s Pond (as reported faithfully/accurately by Dan (Woog, not Katz). One thing I’m sure of: When the “Y” was downtown they knew how to go #2 without making a mess.
Just wait until people find out that at one time we had FIVE movie theaters in town….
An addendum to the Brophy Pool. As young boys, we used to swim in that pool in the nude. No girls allowed when we did. And, as your story suggests, it was also used for swim meets. One morning, an unsuspecting adult came out of the shower room in the buff, stepped onto the diving board and took flight, before realizing that the gallery was filled with swim team parents waiting for the meet to start. Needless to say, that ended nude swimming in the Brophy Pool.
John, you don’t remember me but you were my counselor along with Charlie and Ann Taylor (the sweetheart looker not the women’s wear store). All three of you were superstars of SHS ‘61. We called it skinny dipping back then but since few of us are skinny now we call it swimming in the raw. Hope you’re well.
When I started working at Max’s Art Supplies in 1985 I remember the following,
The YMCA across the street, Shaeffer’s Sporting Goods next to Max’s, Westport Smoke Shop and then it became the candy store with the best hot dogs right in the front window and Beverly and the other woman who ran it, Ship’s on the corner with the best Lobster bisque that you can eat at the bar, Fine Arts 1 and 2 movie theaters right next to Max’s on the left and Fine Arts 3 in the back of the building and Fine Arts 4 where Angelina’s Trattoria is now near BigY, the Town Squire diner where Starbucks is now and the son of the artist Robert Lambdin (Robert’s murals are on the walls in the Patagonia building which used to be the Westport Bank and Trust) , Gristedes supermarket on the right on Main street right up from the intersection of the Post Road, The Chinese restaurant on the corner of Main street and the Post Road, Westport Bank and Trust, The Gallery next to the left of Max’s where George had a huge collection of Al Hirschfeld drawings and original carousel horses in the front window, The old Westport Playhouse (where Toquet Hall is) and the dressing rooms under the old stage that Max’s used for storage and Shaeffer’s Sporting Goods used for storage in the large main room (where a worker from Max’s and I witnessed some paranormal activity as did a girl named Lisa who worked at Shaeffer’s), a few doors down from Max’s were the studios upstairs where Stan Drake, Leonard Starr, John Prentice and Bill Sienkiewicz (who I did some modeling for Bill’s EPMD Business As Usual album cover and as Jimi Hendrix’s manager in the book VooDoo Child, the Illustrated Legend of Jimi Hendrix) did their incredible artwork and famous cartoon strips, the pink Remarkable Book Store, Sally’s Music store on upper Main Street where she had almost every record and if she didn’t have it could get ANY record you wanted within a short time, the old Town Hall building next to Max’s where later when it was being renovated inside I found an old Coleman lantern (dated May 1949) in the dumpster that they threw out, that is now my favorite in my lantern collection. I also remember Art’s Deli across the river where they had pre-made grinders and subs and when you ordered something special they gave you a roll that seemed about 16 inches long with about 5 pounds of deli meat and extras.
I’m sure there are many other businesses and places that I forgot to mention but Westport sure has changed a lot in the 40 years that I have worked in town. This sure was a memory jogger!
Great recall Mr. Cimbak..The only change I would make is that Fine Arts 4 was actually in the complex where Baskin Robbins was (Rt. 1 and Bay) and Post Cinema was in the complex where Angelinas is. I also remember Lisa from Schaefers!
Loved reading this and Dan’s piece today. I’ll play, too. I moved here in 1976. There were 2 pharmacies on Main St (Dorain’s and Achorn) and both delivered. Welch’s hardware. Gristede’s. Oscar’s. Klein’s. All of the movie theaters as you and Dave pointed out. Mechanics and Farmers Bank, which was the only bank around who would give me a mortgage back in 1983 as a newly divorced working mother with a toddler (nope, People’s turned me down but offered the ex a mortgage). Downtown was a true destination then. I haven’t shopped downtown in perhaps ten years now. I’ve driven down Main Street just to look (and fought the silly traffic on the street). Spending a lot of taxpayer money to redo the parking because someone thinks that walking along the river there will be a destination is probably pretty misguided.
Dan, you forgot to mention Woody Klein’s book “Westport Connecticut: The Story of a New England Town’s Rise to Prominence” not sure when this book came out 70s or80s?
2000.
For sure,All these comments here bring back the old memories!!..:-)
Thanks,Dan!!