See you at the Rigger

Good friends and great food come together at the Square Rigger.

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For many Islanders and seasonal visitors alike, the Square Rigger restaurant at the Triangle in Edgartown is as much of an Island institution as the Flying Horses or a sunset in Menemsha. But to totally understand “the Rigger,” as it’s called, it helps to go back well over a hundred years, to what were the desolate Great Plains of Edgartown, where the house that became the Square Rigger restaurant was originally built.

The Square Rigger house has had many owners, among them Manuel S. Duarte, who in 1949 wanted to move the building from the Great Plains to Vineyard Haven, but Vineyard Haven wouldn’t allow the move, so it ended up at its current location, on a lot at the fork between two diverging roads in Edgartown known as the Triangle. “There was nothing on that land back then,” said Tony Rezendes, current owner of the Square Rigger. “In fact, back in those days, you could go for miles out the Edgartown–Vineyard Haven Road, and you wouldn’t find a house.”

While it may not qualify as a scholarly document, there is a history printed on the back of an old Square Rigger menu that claims that Captain Thomas Marshall Pease, a whaling captain, built the house, on the Great Plains out by Edgartown Great Pond, around 1800. And over the years, the house has had a notable history, including a birth, a death … and even a ghost. 

A November 2013 obituary in The MV Times lists the death of Dorothy Mae Gazaille West , who was born and raised in the old Square Rigger house on the Edgartown Great Plains. 

And in Holly Nadler’s book Vineyard Supernatural, Nadler tells the tale of a tragic event that has given the Square Rigger a reputation for the supernatural, even to this day. “Back in its early days [while still on the Great Plains], a family lived in the upstairs apartment of the house,” Nadler writes. “Brothers — 13-year-old twins — shared one of the bedrooms. One night, an electrical storm was brewing over Nantucket Sound. One of the twins stood at the open window, watching the storm move in. He was struck by lightning, and crumpled to the floor, dead. Legend has it that ever since that gruesome night, the upstairs of the Square Rigger has been severely haunted.” 

Jenny Dowd, daughter of Tony and Doreen Rezendes, said, “I used to live in the apartment upstairs, and I could definitely feel something. There was a room I didn’t want to go into.”

For 20 years after the house was moved to the Triangle, it was used for a variety of businesses, including an art studio and an upholstery shop. And then in 1963, John Donnelly bought the property and turned it into the restaurant we all know today as the Square Rigger.

Will Holtham, former owner of the Home Port restaurant in Menemsha, bought the Square Rigger in 1984, and in his Home Port Cookbook, he writes that before he bought the Square Rigger, it was actually more of a lounge than a restaurant, a place for locals to go for a drink or two. And the fact that it was located in Edgartown, where last call for alcohol was 1 am, may have burnished its cocktail lounge bona fides as well. Since closing time for bars in Oak Bluffs was midnight in those days, patrons of Oak Bluffs bars who were not yet ready to call it a night, would make a dash up Beach Road to the Rigger and have a nightcap or two. 

But Holtham, who made the Home Port in Menemsha into an institution, was about to put his stamp on the Square Rigger as well. After 14 years at the Home Port, Holtham was looking to stretch his culinary muscles and expand his repertoire beyond seafood. 

Holtham liked the fact that unlike the Home Port, the Rigger wasn’t seasonal. There was a large enough year-round population to cater to the locals and offer things he couldn’t at the Home Port. So when John Donnelly died, Holtham went to lunch with Donnelly’s sister Anne. “And before lunch was over,” he writes in his cookbook, “I had my second restaurant.” 

When Holtham took over the Square Rigger, it offered only five or six dishes, “but they were all fantastic,” Holtham wrote. Holtham made a few changes to the restaurant, like adding an open hearth, and he expanded the menu to offer specialties like bouillabaisse, and some of the best steaks and chops on the Island. 

Even before Holtham bought the Square RIgger, Tony Rezendes and his family were quietly making their presence felt at the Home Port, starting with Tony and Doreen’s daughter Amy, who spent several years waitressing at the Home Port. In the ’80s Doreen began working as a hostess there, and ended up managing the dining room. And their son Dana started washing dishes at the Home Port when he was 11. “It was part of their slave labor program,” he joked. 

Dana would go on to work his way up the food chain in the kitchen, eventually becoming the “takeout” chef. Tony was not involved with the Home Port or the restaurant business — he was working as a plumber, and had been a part-time employee at the West Tisbury Post Office for about 20 years. But that was about to change.

After operating the Square Rigger for about 10 years, Holtham wrote that it turned out to be everything he could have hoped for. He enjoyed offering menu items he couldn’t offer at the Home Port. And he was fortunate to have a great staff at the Rigger, headed by Aram Berberian, who had started working at the Home Port as a boy.

But when Berberian and his wife decided to move off-Island to seek new horizons, Holtham, who spent the bulk of his time in the summer at the Home Port, suddenly found himself stretched too thin. He looked around for someone who might be interested in taking over the business, but then he decided to look a little closer to home. At this point, Doreen Rezendes was acting as manager at the Rigger, Dana was working in the kitchen, Amy was waitressing there, and their youngest daughter, Jenny, had started waitressing as well. 

“It was Dec. 31, 1994,” Tony said; “I’ll never forget that day. Will said to us, You folks have worked hard, it’s time you owned the place. You can buy the business and lease the real estate — the only money I want is enough to cover my mortgage.” It was the best thing ever when Will made that offer,” Doreen said, “and then four years later, he sold us the property.”

“We went to Dukes County Savings Bank,” Tony said, “and talked to Ted Mayhew, the president of the bank, and they gave us the money. It turns out that Ted used to work at the Home Port himself when he was a kid, washing dishes.” Small world.

They signed papers on Feb. 1, and the transition was seamless. Tony took over working in the kitchen along with Dana. “The tables were turned,” Dana said. “There I was telling my father what to do, but in the end it worked out fine.”

“Cooking came easy to me,” Tony said, “I did the grill, and my son did the sauté.”

“So Tony and Dana were working in the kitchen, Amy and Jenny were waitressing, and I was managing the restaurant — this was truly a family business,” Doreen said.

The menu pretty much picked up where the menu under Holtham left off. “I think we had about 38 entrées on the menu back then,” Tony said. “We offered lobster prepared eight different ways. We offered classic entrées like clams casino, prime rib and baked stuffed shrimp. People could look at our menu and not have to ask what that is.” 

The Square Rigger caters to a healthy blend of seasonal and year-round clientele whom the Rezendeses look on as extended family. “I like to look out in the dining room,” Doreen says, “and see people talking to one another, telling stories and going around visiting different tables. That’s what this place is all about.” It’s also become a home away from home for many members of the Edgartown Yacht Club. “Often they’ll come to me,” Doreen says, “and say, This is our other club.” 

Since the pandemic arrived last spring, the dining room at the Square Rigger has been closed. “Fortunately, we had built up a good takeout business,” Dana said, “so we made a good transition, and we’re going to stick with takeout through this summer season as well. There were a lot of factors that went into the decision; we just felt that this was the safest one. We hope we’ll be opening up the dining room around Columbus Day.”

Which can’t come soon enough for me. I’ve got a date with a Lobster Thermidor.