Tucked away on Hampton Bays’ majestic Dune Road is a family-run dining destination that prides itself on its plethora of fresh fish and hospitality. Oakland’s, which was established in 1992 by a family of the same name, specializes in seafood and sweeping water views enhanced by a glass dining room and rotunda.
Now in its 27th season, Oakland’s was the brainchild of Joyce and Wally Oakland, a couple from Kings Park, Long Island. Wally Oakland had been in highway construction and fencing but had a vision of what he wanted to create. “He always was buying and selling real estate, and he had this vision,” Christine Oakland Hill, Joyce and Wally Oakland’s daughter and Oakland’s co-owner, said.
“We bought some acreage in Hampton Bays, and it was on the water. Somehow, he found out about this property down here, and he just knew what to do. He was definitely a visionary.”
A visionary with a dedication to operating a family business, it turns out. Wally Oakland asked his daughter, in the middle of her college career, if she would like to help him open a restaurant. The rest is, in a sense, restaurant history.
“My parents started the business in 1992,” Oakland Hill said. “It has been run by family ever since.” When Wally Oakland passed away from pancreatic cancer in 1995, the restaurant became the pet project of his wife, Joyce. A few years later, in 2003, Christine Oakland Hill and her brother, Doug Oakland, became partners in the business.
Doug Oakland passed away, also from pancreatic cancer, in 2015. His wife, Stephanie Oakland, assumed his partnership, and she and Oakland Hill now run the business together. The restaurant, which seats 250, operates primarily from April through October, hosting private events, like weddings, in the off-season. The seclusion of the beach has made operating year-round somewhat challenging.
Oakland’s self-identifies as “creative American with a nonstop source of fresh fish.” Indeed, its location —perched on the water, adjacent to a commercial fishing dock — makes for necessarily good eating. “I think the beauty of it is that you just don’t get fresher than fish coming off the boats,” Oakland Hill said. “We’re able to source from the best right here.” To supplement its product, the owners order from local purveyors, like Gosman’s.
The family attributes its longevity — in part, at least — to its view of hospitality. “Service, quality . . . if you’re going to change the quality, people notice that,” Oakland Hill said. “There are less and less family-owned businesses. It’s different than working for corporate. And we all appreciate our staff and all the hard work everybody puts in. Somebody from the family is here every single day. We want to recognize those customers who are here regularly.”
The restaurant treats each meal as a special occasion, recognizing that even just an ordinary night out for dinner deserves to be elevated. In the busy season, Oakland’s can serve up to 1000 customers in an evening, and its staff strives to treat each of these customers as important.
Stephanie Oakland purchased the restaurant next door to Oakland’s, Sundays on the Bay, in 2010, making the lot of land a full-on family affair, and a lasting tribute to founder Wally Oakland. Almost three decades later, the vision that he had for a successful, waterfront restaurant that served fresh fish and more than a small dose of hospitality, has come true. The restaurant is, in the truest sense of the word, his legacy.
“For so many years, you just waited for him to walk through the door,” Oakland Hill said. “He just had that presence.”
Each week The Independent features a local restaurant that has stood the test of time. Each restaurant has been open for over a decade.