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One Family, Four Diners: How Love & Fate Led To Fairfield County Dynasty

Olga Giapoutzis hopes her oldest son Petro will follow in the family business. Photo Credit: Vira Mamchur Schwartz
All four diners owned by Olga and Teddy Giapoutzis sport an original 1950s diner look like Norwalk's the Post Road Diner. Photo Credit: Vira Mamchur Schwartz
They don't make 'em like that anymore. The Post Road Diner boasts its original pie case behind the counter. Photo Credit: Vira Mamchur Schwartz
Olga Giapoutzis favorite menu item is banana french toast. Photo Credit: Vira Mamchur Schwartz
The Bronxville Diner. Photo Credit: Jeanne Muchnick

NORWALK, Conn. – Call it kismet, a good feeling, or just plain luck. Olga Giapoutzis, owner of the Post Road Diner in Norwalk along with her husband Teddy, hadn’t planned on coming to the United States from her native Greece let alone staying, but her father persuaded her to come to Connecticut to help her brother at his restaurant. 

Fate intervened: She met Teddy.

“And that’s why I stayed,” said Giapoutzis.

In 1996, with her husband and his two sisters, the family went into business together and bought the Post Road Diner on Connecticut Avenue, which had been there since 1948.

“When we first got this diner,” said Giapoutzis, “I was not a diner person at all. I was not impressed.”

With little research on her end, Giapoutzis came to appreciate the history of diners in the United States and how they created a sense of community. In fact, she became passionate about it.

Turning the brick-faced Post Road Diner back into the stereotypical American diner –with its retro 1950s vibe – became a labor of love.

“The outside, while all new, is based on the original look,” explained Giapoutzis. “Our pie case, for example, is the original old pie case. We keep fixing it and fixing it. It’s so beautiful; they don’t make things like that anymore.”

Once her sisters-in-law left the business, Giapoutzis and her husband expanded and bought the Driftwood Diner in 2008, a scant few miles down the road in Darien. Renaming the eatery to the Darien Diner, the couple kept the business there for seven years. 

Then in 2009 at the Darien Diner, an agent approached Giapoutzis and asked if she and her husband would consider opening a place in New Canaan; she had a space.

While not interested at first, Giapoutzis nevertheless decided to take a look.

“It felt right,” said Giapoutzis.

And so, the New Canaan Diner was born. But the family wasn't finished.

“For five years we kept eyeing the Friendly’s property, [on the Post Road] in Darien” said Giapoutzis. “Every time we drove by it, we wanted it, we felt it was for us.”

The first day the sign went up in 2015, Teddy was on the phone; by the end of the day the property was theirs to lease.

But the Giapoutzis duo weren’t done yet.

Lightening struck twice, you could say, when they were approached again, this time at their New Canaan diner in 2015, about opening a diner in Bronxville, N.Y.

“I told my husband he was crazy to consider it,” said Giapoutzis. “He told me to look at the place and the decision would be mine.”

Needless to say, as she had with the others, Giapoutzis fell in love with the Westchester spot. The Bronxville Diner, styled with the same retro feel as its Connecticut siblings, opened in 2016.

All four diners offer the same menu. Although Giapoutzis says “healthier” food seems to be the customer favorite in Bronxville and New Canaan, while Darien and Norwalk tend to go for the comfort foods.

And there's a new family face that greets and charms customers. Giapoutzis' 19-year-old son Petro can be found working at the Post Road Diner and she is hopeful he will take it over one day.

“I don’t want my children to give this up," she said. "There's been a lot of love put into each one."

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