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Greece Stefanopoulos
Photos courtesy of the Stefanopoulos family/ respective businesses.

The Stefanopoulos Family Crafts a Legacy in the Hudson Valley

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Take four siblings from Greece, one secret pizza recipe, and an infinite work ethic, and what do you get? A robust family business that anchors the Hudson Valley with food and fun.

The four original Stefanopoulos brothers—Billy, George, Nick, and Peter—and four of their children run an empire that’s become a touchstone in so many Valleyites’ lives. There are nine Pizza Inns (eight in the Hudson Valley, plus one outlier in Great Barrington), which have served 80 million customers and counting. There’s also Hotel Caravana, a beloved drive-in and airstream hotel in Amenia, the gracious Millerton Inn, a salad dressing company, and a soon-to-open eatery in Millbrook.

The four brothers: Peter and George at left, Billy and Nick on the right.

The four brothers: Peter and George at left, Billy and Nick on the right.

Coming to America

This dynasty, however, was born of hard times when the brothers were young men in southern Greece. As John Stefanopoulos (son of Billy) tells it, the siblings’ father got badly scammed. Reeling from this setback, the quartet set off to America to find their fortune.

Get your fill of snacks at the drive-in.

Get your fill of snacks at the drive-in.

Settling first in Connecticut, they grabbed whatever jobs they could. The food industry was hospitable to recent Greek immigrants, and they did everything from working in a cheese shop to driving an ice-cream truck. After a couple of years, the brothers decided it was time to do things their way. They’d either find success in the U.S. or head back home, where the rest of the family and their farm were still anchored.

They began buying and building restaurants, drifting from Connecticut into the HV. “We love the land here,” says Peter. “When people visit from Greece, they expect a crowded city. Then they see the Hudson Valley, and they get it. They say, ‘You live in heaven on earth!’”

In Pursuit of Pizza

The brothers had a knack for knowing when and where to open restaurants. One of the eateries they purchased was a pizza shop, and soon they were off and running. The owner offered to stay on for a bit and teach them the intricacies of pizza dough, but the brothers didn’t need any guidance. “We have a secret recipe, so we can’t tell you everything,” says Nick with a laugh, “but we do have a special process for the way we handle our dough, and it has that special ‘Grecian touch.’ Greek pizza is different from Chicago, New York, or Sicilian.” The pizza is deeper-dish than the usual NYC slice, but not as dense as those beloved in the Windy City.

You can purchase Four Brothers’ famous Greek dressing to jazz up salads at home.

You can purchase Four Brothers’ famous Greek dressing to jazz up salads at home.

Their recipe was perfected in 1974, but it wasn’t just the taste (and options with goat cheese and feta) that would be their signature. They also wanted their pizza place to differ from the usual grab-a-slice-and-go vibe. They created a relaxing setting with comfy seating, artwork, and plants. Two locations, in Dover Plains and Pleasant Valley, opened in 1976, and soon other locations were popping up throughout the region.

Yes, the pizza was—and is—delectable. But there were plenty of other dishes for those not in the mood for a pie, including salads with their signature dressing, which was so craveable that it became its very own business. “Most restaurants offer you maybe 15 different dressings,” says Peter. “Not us. Just one. It’s that good.” (The pizzas are no slouch either—they are baked, frozen, and shipped nationwide. There’s even a pizza subscription for those who are legitimately addicted.)

The family worked 24/7 to make sure they were delivering top-notch service as their business flourished. And they still do: Stop into any of the Pizza Inns, and you are likely to find a Stefanopoulos present at some point during the day. “We always do a morning meeting in Amenia before we split and take off to various locations,” says George, “and at night we regroup and do a big feast, all our families. This is a lifestyle, not a job.”

And the community has embraced the brothers and their restaurants, reserving them for birthdays, anniversaries, graduations, and every other kind of celebration. Being part of the lives of their clients has been a highlight for the brothers. “We’ve developed some of the best friends over the years,” says Billy. “Some customers have been coming to us for nearly 50 years—and that means the world to us.”

How to Succeed in Business

But, of course, everything is not always rosy when trying to build a business and a brand in changing, challenging times. And doing so with your closest relatives. “Painting the long-term vision and keeping discipline through wavering times…it’s not easy to go through generational changes and not change your product,” says George. “We’ve been fortunate that we believe in what we do and what we sell.”

Possibly the most important lesson they learned was to stay out of each other’s way. Too many family businesses have ended with siblings not on speaking terms or with “Succession”-style fall outs. But the Stefanopoulos’ have sidestepped that scenario. “We’re four brothers, and each has his own position and title. This way, everyone is happy,” says Peter.

One thing they never forget is the thread that weaves the business together. “We love entertaining and taking care of people,” says Billy. “To us, it’s still the same business, whether you make pizza or have a drive-in.”

About that drive-in: It’s an example of how the younger generation is deeply involved. The whole family cooked up the plan, with the kids of the four brothers loving the idea of using some extra acreage on the Amenia property for a drive-in. They brainstormed what they would want and what would make it the coolest spot in the county. And that may well be what you find there: the latest blockbusters, plus a snack shack serving everything from lobster rolls to margaritas to soft-serve cones. (There’s even the aforementioned Hotel Caravana, which rents airstreams, if you feel like rolling straight into bed after the movie.)

A boho chic camper at Hotel Caravana.

A boho chic camper at Hotel Caravana.

Next up for the family business is a California-meets-Mediterranean restaurant on Millbrook’s main drag, where former bistro Aurelia once was. While the family won’t reveal the name or menu just yet, it promises to be a fresh take on dining out.

The Property Brothers

The Stefanopoulos’ all live on a family compound. The four brothers, with wives Vicky, Olga, Katina, and Eleni, purchased 60 acres in Amenia. There, each family member has their own home. There’s also a chapel, gardens, a vineyard, and a farm.

In fact, farming has been all in the family for generations, both in Greece and the Hudson Valley. The New York farm has provided their own restaurants as well as those in Manhattan. “We used to have 550 goats and make our own yogurt, goat cheese, and feta,” says Peter. They still grow mint and basil there and do a bit of dairy; the olive oil used in and sold at the restaurants comes from the family orchards in Greece.

When the brothers have a scrap of free time, they’re just like anyone else in the region wandering through antique stores and boating on local lakes. With all they’ve worked for and everything they love right here in the Valley, there’s not need to wander far from home.


Related: This Greek Grain Salad Recipe Is Healthy & Delicious

Hudson Valley Restaurant Week is back this April 8-21!