Everyone’s Westport is different.
Our image of the town — what it is, and should be — is formed by our first experiences here.
Mine dates back to the 1960s, when I was in elementary and junior high school.
Those who arrived later — by birth, as kids or teenagers, or adults — have a different idea of “Westport.”
A woman recently lamented how much has changed. She misses the mom-and-pop shops on Main Street, and the small-town vibe.
She moved here in 2010.
That was a dozen years after the New York Times published a story headlined “Is Heart and Soul Gone From Main Street?”
In 1998, the New York Times had a stand-alone Connecticut section. This Page 1 photo shows Main Street, with Oscar’s Deli (center) and then-closed Remarkable Book Shop (right). The inset is Klein’s.
Nearly 3 decades ago — on December 27, 1998 — Leslie Chess Feller explored the changing nature of our town. She began:
Little shops, once the backbone of Main Street in Westport, have almost disappeared. One of the last is Klein’s, founded by a Hungarian-born entrepreneur named Henry Klein who took pride in greeting every customer by name, which has for 61 years sold books, stationery and office supplies. Mr. Klein worked until the day before his death in 1990, at the age of 90.
But in January the store will be subletting ground-floor retail space to the Banana Republic chain, one of many that have displaced family-owned Mom-and-Pop stores by being willing to pay higher rents.
Spoiler alert: Banana Republic is gone now too. So is Oka, the furniture store that took its place. The upper part of Klein’s — where you could buy office supplies and typewriters (kids: ask your parents what those were) — has been repurposed as Sushi Jin.
Banana Republic replaced Klein’s.
Robert Hertzel — vice president of Klein’s, and president of what was then called the Downtown Merchants Association — said, ‘We have turned into a regional shopping center. But that’s not a bad thing.”
Klein’s, in the 1962 Staples High School yearbook.
The piece continues:
Another holdover is Jack Swezey’s jewelry store, currently run by his son David. ”We opened here in 1956 when everybody knew everybody and each store was one of a kind,” said Mr. Swezey. ”Business is good, but sometimes I feel like a loner,” he added, looking out his shop’s window, now facing Williams-Sonoma, Brooks Brothers and Crabtree & Evelyn. ‘
‘Today’s Main Street has become an outdoor mall,” he said. ”I’m one of the few individual merchants left and that’s because we own the building.”
Swezey — where an enormous model train set entertained passersby every Christmas — is today the site of Brochu Walker.
Swezey Jewelers
Williams-Sonoma is still here, but in a location (Bedford Square) that did not exist in 1998. Brooks Brothers is still here — though next year, Sephora takes over. Crabtree & Evelyn sold its last loofah in 2009.
Plumed Serpent owner Fred Tow talked about his move to Playhouse Square, after 25 years on Main Street. (The bridal gown boutique has since moved again, across the Post Road.)
”When I opened in 1971, Ann Taylor was the only corporate store,” Mr. Tow said, ”and my monthly rent was $325.” By 1996, the chain stores had moved in and his rent jumped to $5,700 a month. Mr. Tow said that customers now have to go to Kent and New Preston for the look of old-fashioned Connecticut.
”In terms of both merchandise and decor,” he said, ”unless they see the sign, shoppers can’t tell whether they’re in J. Crew or the Gap. It all seems the same. There’s this corporate coldness, a lack of personal connection. People don’t realize what’s been lost.”
The 3-story Gap replaced a failed vertical mall — which was built on the site of a furniture store that burned down in the mid-1970s.
The piece continued with reminiscences from Howard Munce. The artist — then 83 years old, who first came to town in 1935 (and died 10 years ago, at 100), remembered Greenberg’s (“where you could buy anything from buttons and thread to underwear and Girl Scout uniforms,”) Charles Market, and the Ben Franklin 5-and-10 (kids: ask your grandparents).
In Howard Munce’s day, Welch’s was one of 3 hardware stores on Main Street. Traffic was 2-way all the way to the Post Road, too.
Feller continue:
In the last three decades, however, Main Street has morphed into a sort of Rodeo Drive East. Dubbed the ”Golden Half Mile” by the newspaper columnist John Capsis, who died in 1997, Main Street’s chain stores and boutiques are staffed by people who commute from other towns. As they talk on cell phones, the drivers of S.U.V.’s, BMW’s, Jeeps and Jaguars fight for parking spots. Tourists clutch shopping bags sporting logos while undercover police officers pursue what they say are organized gangs of shoplifters.
The story continues, bopping down Main Street’s favorite side road, Memory Lane.
Feller writes about the Remarkable Book Shop, which closed in 1994. Remarkably, after Talbots it was replaced by Westport Local Market, now Eleish Van Breems — both local, one of which even had the word in its name.
The Remarkable Book Shop. Too bad this does not show its vibrant pink color.
Leann Enos, an actress and theatrical director who moved to Main Street when she was a child, and whose father owned Walker’s Frame Shop, said, ”To me, it feels as if Main Street has lost its heart and soul. Now everything is about spending money.”
Anne Rowlands — a Westport native, and vice president of the Westport Chamber of Commerce — said she could no longer afford to shop on Main Street.
”It’s gotten so expensive and, to be honest, it feels kind of faceless to me,” she explained — not exactly a Chamber of Commerce-type comment. “It’s rare to find someone you know.”
Downtown shopper Linda Stern said, ”At first, I missed the mom-and-pop stores. But now it’s very exciting; there’s an energy to the street.”
Meanwhile, Predrag Vicvara, a Fairfield resident who had lived in Croatia, said, ”You find different nationalities here. It seems a little bit European to me. I like it. It’s nicer than the mall.”
Main Street: a bit of Europe?
Sharon Rosen — who moved to Westport 5 years earlier, and “considers Main Street an asset despite the chain stores” — had the last word.
”It’s convenient,” she said. ”I understand it was very quaint and lovely here once.”
That was the view 28 years ago — near the end of the 20th century.
Folks rued the demise of mom-and-pop stores then. They still do, 30 years later — even if they arrived after 1998, and believe there were plenty of quaint mom-and-pops when they came.
Downtown Westport was evolving 3 decades ago. It was when my parents moved here in 1956. It continues to evolve today.
What’s “your” Westport? When did you come to town? What’s changed? What hasn’t?
And how will your comment look when we look back on it 28 years from now, in 2054?
(“06880” often explores the changing face of Westport. If you enjoy stories like this — or anything else on our hyper-local blog — please click here to support our work. Thanks! PS: See you on Main Street!)
Well there is one hold out! Mitchell’s! Bill and I graduated from Staples in 1961, played football together and have remained friends these many years. My mother bought my first Westport styled clothing when we moved here from rural Western Kentucky in 1958. I had arrived at Staples in Levi’s, a White t-shirt white socks and loafers. The James Dean look. Not for long however! Thanks Dan!
My cousin Susan Parise was in the class of 1961, the first class to complete all three years at the new Staples on North Avenue.I believe Mike Backiel was in the class of’61 as was Bill Burge.Anyone remember them? Also, if you’ve noticed , lately I’ve been quoting previous posts by Dan. I happen to have them memorized- give me a date and I’ll give you some information on that day’s posts.
Let’s not forget Country Gal and Selective Eye (the coolest store on Main Street).
Thank you as always for sharing these fabulous pictures. We moved here in 1996. I was so thrilled to have a movie theater right downtown and the remarkable bookstore in pink put a big smile on my face. Fast forward 30 years times are always changing and moving forward, that’s called progress. The one thing in the picture I loved were all those beautiful awnings. We are blessed to have a no vacancy downtown shopping center filled with design stores, clothing stores and great dining etc. so I will not complain about progress. It is inevitable
Times are always changing and “moving forward”. If things get better, we call it progress. If things get worse, we call it something else, and likely something not suitable for a family friendly blog like 06880.
I’m dizzy with the new downtown. I miss Mr Klein greeting us at the door, the comfort of looking at a book at Remarkable, going to a movie right there. I’m not one to browse and not one to spend money on an unnecessary object. So now I’ve become at Amazon shopper.
Was it Welch’s or Westport Hardware that sponsored our Little League team in the mid 60’s? Gristedes is where my mom would send me on my bike, or maybe I hitchhiked, to pick up groceries. I’d just sign her name and I think they sent a monthly bill! There was a candy store on Post Road near Main Street. Most of the money I made delivering papers, shoveling snow, pumping gas, selling flower seeds, was spent on slices at Westport Pizzeria.
Dan posted a picture once at the corner of the Post Rd. and Main Street. Two horses were drinking water from a water trough and one man riding his horse was wearing a Covid like mask, which put the picture around 1919 when the Spanish flu pandemic hit. The same corner 107 years ago. My grandfather came downtown with a horse and a buckboard too around that time period.
My sisters and I loved coming to Ann Taylor in the late 60s? from Stamford, where we lived. Westport and Main St. seemed so sophisticated and pretty! Fast forward 30ish years when my husband and kids moved to Westport. Those early shopping days really made an impression. But no more Ann Taylor 🙁 (and we moved back to the city).
Dan – Love your opening (and as always, insightful) anecdote regarding the town resident lamenting how much “downtown” Westport has changed – and she first moved here in 2010. That’s what I came to learn when I first became involved in this perennial favorite topic: Main street was so much better in the “old days”; only everyone’s version of when were the old days sure does vary!
Mine is probably set in the Westport of the 1970s – and I can hear my kids saying “OK Boomer” now . . .
Once you get past the “why couldn’t we have ‘kept’ such and such a store or restaurant in Town forever” lament, the ‘mom and pop’ vs. chain stores on Main Street topic is real, and not unique to Westport. Part of the problem, of course, is Main street is a victim of its own success – desireable space Main St means market rate rents now easily exceed what locally-owned businesses can afford. But the town planners have other levers to pull on Main St – like limiting maximum store size, and incentives to bring restuarants to the downtown area to maintain some vibrancy after 5:00 pm after losing movie theaters and the Y. That has paid off.
But no place is frozen in time like some kind of snow globe . . . now then, let’s talk about how much better Downtwon was in the [my] old days – Ships, Soups On, Bill’s Smoke Shop, Sport Mart, Schaefers Sporting Goods, Kleins, Baskin Robbins, 4 movies theaters . . . 🙂
“I understand it was very quaint and lovely here once.”
That about sums it all up.
I recall there were 4 Fine Arts theaters in town and the single “the post cinema” on the post road.
I’ve been in Greens Farms since 1995 – not nearly as long as a lot of people. I think the beginning of the end of me thinking about trips downtown (as a broad destination) was when the movie theaters closed. We could plan for dinner and a movie – and go early to shop. The hassle of traffic and parking was a comparatively small part of the trip. Now it is the same hassle with less to do.
After that, I would still shop there /maybe/ two or three times a year – not spend a day shopping, but specifically heading to one retailer. Post-pandemic, I don’t think I’ve stopped in a downtown retailer even once annually. (I confess that one of the current businesses you named didn’t even slightly ring a bell.)
I don’t speak for anyone else in this part of Town, but I think of my community being much more Greens Farms/Southport/Greenfield Hills and the west side of Fairfield. Outside of when the tax bill comes due, town limits are kind of incidental to my activities.
Yes, inevitable. But I love to read about the “old days.” We moved to Westport in 1954. Of course all those Main Street stores remain in memory. Dorain Drug (with the two phone booths in back) and Klein’s; both were stores where you’d be greeted by name and would just “charge it.” The dry cleaner and other stores with entrance/exit back and front. Greenberg’s and Trudy Gary. Charles Market with the sawdust on the floor. It was a lovely town and I probably didn’t appreciate it as much as I might have!
My current New England home town is experiencing the same change/nostalgia. Thanks as ever for memories Dan.
Like you Dan my Westport memories are primarily tied to the 60’s & 70’s. I’m a Gen 3 Westporter and even had a couple of teachers who had my parents as students.
My dad owned the hardware store in Bridge Square so my sister and I spent a lot of time in Saugatuck and have fond recollections of the stores and restaurants in the area; getting a snack at Peter’s Bridge Market or Frannie’s. Getting a haircut on Riverside Ave. or fishing off the bridge and behind the firehouse, also occasional dinner’s out at Mario’s, Manero’s or The Arrow.
Downtown, Klein’s was the go-to place for so many things a kid would want. They had a great toy department in the back and later as teens picking up a new album or paperback (not to mention Cliff’s Notes). I used to get my tennis racquets strung at Sport Mart or Schaeffer’s, and who back then didn’t love having three movie theaters to choose from? I was a regular customer of Ed Mitchell’s as a high schooler (though the place was never the same once they moved into their new building) and I remember going with my dad and sister to buy gifts for our mother at The Little Shop and Country Gal to name a few.
Nothing stays the same and it’s puzzling to me why people from the city who move to Westport drawn by its many charms then want to turn it into Tribeca or SoHo. Nonetheless it will always be home to me and I wouldn’t trade having growing up in Westport for anything.
Well, I go waaaaay back but lots of the memories mentioned here I remember. I am Staples 1958. The last Riverside class. I was trying to remember earlier the name of the drugstore and the Barber shop. I thought I remember Wheelan’s for the drugstore, but I could be wrong. We could get the city bus in front of Asension Church to take us home but frequently walked to Wheelan’s or? It was a social time, and a boy just might offer to buy a girl a coke. Just up the street before the Fine Arts Theater was, and here I hope my memory of the name is correct: Jimmy DeMaria’s Barber Shop. He always said that we had a connection because his son’s plane went down during WWII the same night my brother was born. Just up Main Street was Bill’s Smoke shop that had lots of Penny Candy! Don’t forget the YMCA with its indoor pool where you could go to take lifesaving classes and also dress up and take Ball Room Dancing lessons from Miss Comer. Yes, those were the days my friends and they did evolve and change even though we remember them fondly. Back in the day the rich and the famous did mingle with the working class. Everyone was friends and helpful. One of these days I am going to send something to Dan about on particular Westport resident that did so much do quietly for so many people.
Thanks, Mary. I think the drugstore was Colgan’s.
And sure, send the story along!
My family moved to Westport when my parents got divorced from Sands Point, LI. In 1965. I started 8th grade at Long Lots Jr High (your class and home room, Dan) that year.
I can talk forever about what’s come and gone so here’s my input to this story.
From Memorial Day – Labor Day there were “Summer People”.
Summer traffic consisting of trailers, boats, and much traffic.
Folks were different – not so friendly and you’re not as likely to run into people you know as much.
I watched over the years as summer people became year round. Summer homes eventually knocked down made way for year round colonials and split levels, Raised ranch homes, then those coming down replaced by the McMansions in the 90’s….you all know the rest!