Restaurant Churn? Not These!

A recent “06880” photo of the Compo Beach palm tree got an alert — and hungry — reader thinking about lobster rolls.

That reminded her of clam chowder, which made her think of Westfair Fish & Chips. She’s been a fan ever since she was a student at Staples High School, back in the mid-1980s.

The small, unassuming takeout-or-eat-in spot behind the strip mall opposite Stop & Shop has been a Westport favorite for over 30 years. And that got the “06880” reader wondering about other restaurants that have stood the test of time.

Three decades is a great achievement for many things: a career, a marriage. But it’s particularly remarkable in the constant churn that is Westport’s restaurant scene.

She and I came up with a list of places we think have been here for at least 3 decades. They include:

Gold’s. The anchor of Compo Shopping Center since it opened in the late 1950s, and the anchor 6 decades later for anyone who loves a quintessential deli.

Viva Zapata. Probably the oldest continually operating restaurant in town, especially when you consider its predecessor, at the entrance to what is now Playhouse Square.

Westport Pizzeria. Opened in 1968 on Main Street, where it stood proud and unchanging for over 45 years, “Westport Pizza” moved around the corner to the Post Road in 2014. Its special recipe thankfully remains the same.

The Black Duck. A star turn on “Diners, Drive-Ins and Dives” has not changed this waterfront favorite one bit.

(Photo/Chou Chou Merrill)

Dunville’s. Around the corner from the Duck on Saugatuck Avenue, another down-home place that’s the same now as when its present owners grew up here.

Sherwood Diner. Or, simply, “the diner.” It’s no longer open 24/7, but is still the go-to spot for Staples High School seniors, senior citizens, every other human being in Westport, and anyone wandering in off nearby I-95.

(Photo/Lynn Untermeyer Miller)

Sakura. As steady as she goes. It — and the gorgeous cherry blossom tree outside, which gives the restaurant its name — has been a fixture opposite McDonald’s since the fast-food franchise was Roy Rogers. And before that, Big Top.

Fortuna’s. With limited seating, this is not really a restaurant. But stop quibbling. Its winning formula has filled the stomach of Staples students, Post Road workers and everyone else since the Ford administration.

Coffee An‘. If it’s good enough for Bill Clinton, it’s good enough for the rest of us. It doesn’t matter if you’re a president or a peon. The donuts are the same — unbelievable — for all.

Little Kitchen. When it opened on Main Street, it really was a “little kitchen.” Now it’s bigger, and the granddaddy of all Asian fusion places in town.

Da Pietro’s. One of Westport’s best — and smallest — restaurants, earning praise and love since 1987.

(Photo/Katherine Bruan)

Tavern on Main. This cozy 2nd-floor Main Street spot has not been here as long as its predecessor, Chez Pierre — but it’s getting close.

I couldn’t find out for sure when a few other long-lived (though probably less than 3 decades) restaurants opened. But these too have stood the test of time: Tengda. Tarantino’s. Finalmente. Via Sforza. Planet Pizza. Tutti’s. Positano’s (at 2 different locations).

Special mention goes to 2 fantastic delis that offer a wide variety of hot and cold food, and serve as community centers: Elvira’s  and Christie’s Country Store. 

Plus, of course, Joey’s by the Shore. It’s not a restaurant or a deli. But the beach concession occupies its own special. much-loved niche. And if it hasn’t been here for 30 years, it’s at least 29.

Finally, 2 other downtown delis have been around for decades. They’ve changed names, and — particularly with one — substantially updated the interior.

But Rye Ridge (formerly Oscar’s) and Winfield Street Coffee (previously Art’s, and definitely not on Winfield Street but right over the bridge) keep doing what their predecessors have done.

And what every other place in this story does: provide excellent food and continuity to generations of Westporters.

(Have I missed any longtime restaurants or delis? Click “Comments” — and my apologies!)

54 responses to “Restaurant Churn? Not These!

  1. Bunny Franco

    Calise’s on post road

    • Good call. They’ve been there for decades. I may be wrong, but I think they started as a grocery store, and added the deli 20 or 30 years ago.

      • Michael Calise

        Calise’s was started in the late 1920’s by my grandfather as Westport Fish & Poultry Market on the “West side of the bridge” My father took it over in the thirty’s and changed the name to Calise’s Food Market. In 1954 he moved it to it’s current location. In the late 1980’s he sold it to my Son-in-Law Carmine Cenatiempo who transformed it to a Delicatessen. It is the oldest operating Westport Food Business. In your old truck traffic picture of a few days ago you can see a Calise’s Liquor Store sign, also started by my Grandfather which is now next to the Market and is Westport’s oldest operating Liquor Store. The grocery store hidden by the truck was across the street.

        • Thanks, Michael, and congratulations. My apologies for not including Calise’s in the original story. My parents were longtime customers, beginning with their move to Westport in 1956. And I am a huge fan of Carmine, who is so helpful in many ways to Staples High School.

        • Pegeen Gaherin

          I loved your Grandfather, Grandmother& Aunt a constant presence at the store.
          Your Grandfather was more the calm in the storm.

          But oh boy, those Matriarchs were something nothing slipped by them.

          I miss the previous generation.

          All the best,
          Pegeen Gaherin

        • Pegeen Gaherin

          I loved your Grandfather, Grandmother& Aunt a constant presence at the store.
          Your Grandfather was more the calm in the storm.

          But oh boy, those Matriarchs were something nothing slipped by them.

          I miss the previous generation.

          All the best,
          Pegeen Gaherin

  2. Has Da Pietro been here that long? I’m sure Pearl’s was in that space well into the 90’s.

  3. Matthew Mandell

    Loved this piece. What a great bunch of places to go to.

  4. It’s mind-twisting to read of places w/ 30 yrs history and that began in Westport after I left (1985).
    And it’s heart-bending that places I loved(!) are long-time gone: Clam Box, Dameon’s, and Chubby Lane’s,

  5. Hi Dan…,not sure but I believe Angelina’s deserves a spot on this list.

  6. Jack Whittle

    Now here’s another great Townie post Dan – and note, Westfair Fish & Chips was first started by a former Clam Box cook after that place went out.

  7. does Sherwood Diner make the list? 1977

  8. Does Carvel count as a restaurant?

  9. Jeffrey Wieser

    Thanks for this fabulous, fun post. I think I’ll plan a tour – like going to all the major league ballparks – only different !

  10. What about Tiger Bowl? It’s been around for a very long time. Does it make the 30 year cut?

  11. Prill tells me Carvel has been here since at least the 1970s but it’s not a Deli. Hahaha. Just ice cream but my wife thinks ice cream is a food group! Mike

    Sent from my iPad


    • It was here in the 1960s, if not earlier. Hasn’t changed one bit, except that the enormous ice cream cone is no longer on the roof.

      • Michael Calise

        Fred Faltings an early Carvel pioneer moved his family from Long Island to Westport around 1950 and opened the Carvel store at its current location.
        They featured the newly launched Flying Saucers, an instant hit, and not to be believed Banana Splits! Over the years the Faltings family has provided employment opportunities for hundreds of staples students. The store is still owned by his daughter Ellie (Staples 56)

      • Bob Stalling

        Actually, the front wasn’t enclosed…there was an outside walk up window. The front was enclosed sometime in the early 70’s…

  12. Patty Kondub

    To correct Jack Whittle, my dear fellow Staples grad—Westfair Fish & Chips was actually started by Craig Sternberg who was a cook when I worked at Mansion Clam House…not the Clam Box..after the Mansion changed hands.

    FUN FACT In those days from 1979-1981 the owners of The Mansion Clam House, the Verina’s, let us Staples High School field hockey and basketball athletes return all the empty beer bottles for the nickels as a fundraiser!!

    • Jack Whittle

      sorry [my good friend] Patty, but Craig (a great guy) didn’t “start” Westfair Fish & Chips; he will freely tell you he took it over.

      • Brian Sternberg

        Sorry jack! Patty is 100% correct as my father started Westfair fish and chips in 1985… Prior to 1985 and the start of westfair, was a restaurant that had maybe lasted a year and a half called “Down East.” … now to tie the “Clam Box” into all of this. The owner of “down east” [ralph mitchell] had previously worked at the “clam box” as the maitre d, bringing some influence into the mix. With that and the Help of my father’s previous years at the “mansion clam house” he decided to start this 30 plus year adventure in 1985 opening westfsir fish and chips.

  13. Mary Ann Batsell

    What about Fortunas? I’m not sure
    but I think that makes the 30 year

    • Of course. Which is why I included it in the middle of the story, with not only this text — “Fortuna’s. With limited seating, this is not really a restaurant. But stop quibbling. Its winning formula has filled the stomach of Staples students, Post Road workers and everyone else since the Ford administration.” — but also a photo!

  14. I realize S & S Dugout is not within Westport’s borders but it’s so close to the line—and it’s in a stretch of the Post Road in Southport that I believe is frequented by Westporters who live on that side of town. Speaking of which, I’m pretty sure it was Neil Brickley who introduced me to this quintessential mid-century luncheonette. And I think S & S Dugout has been around longer than virtually all of the others listed above. If you’re willing to expand the boundaries slightly, I hereby nominate S & S Dugout.

    PS. I remember eating there with at least a couple of the guys after our FCIAC championship in 1970.

    • Sorry, Fred – strict boundaries for this one. The slope is too slippery to start talking about this, and Garelick & Herbs, and …

  15. Mary Ann Batsell

    Sorry Dan, somehow missed it!

  16. Angelina’s Pizzeria in the Post Plaza opened before I graduated in 1981 serving consistently great Neopolitan pies. Plus they donated my winning gift certificate to this year’s Yankee Doodle Fair. Mille grazie!

  17. My wife and I have lived in Westport for over 30 years and it seems like most of our favorites over the years have vanished. This survivors list is actually longer than I might have guessed but not as long as I wish it could be. Great and well-researched article – thanks, Dan.

  18. Tom Duquette, SHS '75

    Back in the mid-70’s while working for my father at Jerry’s Hardware in Saugatuck’s Bridge Square a young guy came in one afternoon named Duke. He told us he was opening a Mexican restaurant across the street and wanted to apply for store credit. My dad (an Archie Bunker type) was skeptical about this longhaired dude but agreed. Duke and his crew worked hard and sure enough got Viva Zapata opened for business. We got a couple free lunches too and this was my introduction to Mexican food which was pretty darned good. Back then who would have guessed that ‘Viva’ would have enjoyed such longevity in a small New England town like Westport? Congratulations Viva.

    • Bob O’Mahony

      Tom, stop in an introduce yourself. I’ll buy you a drink and some tacos. The gift that keeps on giving. Lol

  19. Dominic Santella

    Coffee An…Best donuts…Period.

  20. This is a wonderful testimony, Dan. Establishments like these have longevity for a reason. And they are part of our unique character.

  21. I was unsure but just confirmed it: the Organic Market has been around for thirty years.

    • Whoops—no. It’s been around a lot longer than that!

      • Another great one that I missed. And it’s about 50 yards from where I live.

        • Linda Gramatky Smith

          I remember my mother (Doppy Gramatky) often went to the Organic Market around 1980-1982 with a young neighbor from Colony Road, Audrey Balas. That would make it 37+ years old.

  22. Sakura’s owner told me his place was Westport’s oldest sit-down restaurant. He added that the Sherwood Diner was next.

  23. Jeanine Esposito

    Love this profile, Dan. When our Airbnb guests ask for Rec’s there are at least 4 on this list I always recommend and people love them…

  24. Arthur C Schoeller

    I would vote to add Carvel’s. Ice cream is an essential food group.

    • Well, if ice cream is an essential food group, then so is wine, which counts as a serving of fruit. There are a number of “package stores” going back over thirty years, such as the Greens Farms Spirit Shop.

  25. Does anyone know what happened to Juluan’s Pizza next to Harvest and across from Zapata?

  26. Caryl Beatus