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Those looking for a special venue for a fundraiser, one that boasts a breathtaking view of Shinnecock Bay, were usually directed to Doug Oakland.As a result, Mr. Oakland and his wife, Stephanie, hosted scores of community and school-related fundraisers over the past two decades at their Dune Road establishment, Oakland’s Restaurant and Marina. Friends said that was because of their generosity—the Oaklands always made a point of ensuring that those hosting an event at their establishment made some money—and the welcoming atmosphere of their waterfront eatery.
Lars Clemensen, superintendent of the Hampton Bays School District and the former president of the Rotary Club of Hampton Bays—both of which have held fundraisers at Oakland’s—said this week that the restaurant remains a highly desired venue for community fundraisers because of its “Hampton Bays” feel. And Mr. Oakland, he added, was a huge part of that.
Mr. Oakland, whom Mr. Clemensen described as a “fierce promoter of Hampton Bays,” died last Wednesday, July 1, after a battle with pancreatic cancer. He was 52.
“He was somebody who always stepped up to the plate, and whenever anybody was in need of something, he was the first one to help them achieve their goals … whatever it would be,” said Southampton Town Councilman Stan Glinka, a friend of Mr. Oakland for many years and a former president of the Hampton Bays Chamber of Commerce.
Those who knew Mr. Oakland, who celebrated his 52nd birthday on June 26, said they were always impressed with how hands-on he was with his business and his other part-time job: serving as a member of the Hampton Bays Board of Education. Mr. Oakland served on the board for six years, from 2007 until 2013.
Stephanie Oakland, Mr. Oakland’s wife, said her husband always had a strong work ethic, opting to do whatever needed to be done himself rather than hiring someone else to do it.
Mr. Oakland, who served as president of the Hampton Bays Board of Education for five of the six years he served, also helped oversee several major construction and renovation projects at the district. It was during his tenure that the new bleachers and track were installed at the high school.
“Everything he did benefited the kids of Hampton Bays and future generations,” said Dot Capuano, president of the Hampton Bays Chamber of Commerce and also a friend and neighbor of Mr. Oakland. “He’s really a front-runner.”
“He was a great, great support in the school district,” added Mr. Clemensen. “He really wanted the best for the Hampton Bays schools.”
If they could use only one word to describe Mr. Oakland, those who knew him the best said they would call him a “giver.”
“He was on the Board of Ed for years, running a business while he’s doing that,” said Ms. Capuano’s husband, John Capuano. “He meant a lot to a lot of people. He was a giver in every aspect of life.”
Mr. Capuano, who docks his boat at Oakland’s, noted that it was nearly impossible to recall a time that he was down by the water and Mr. Oakland wasn’t there.
“He was the guy that owned the marina and he’d be there before me in the morning—and I’d get there at 5:50—picking up litter,” Mr. Capuano said. “He was always there.”
Mr. Oakland’s love of boats and the water goes back to his childhood, according to his mother, Joyce Oakland of Hampton Bays. She explained that her two sons, Doug and Gary, started fishing with her late husband, Wally, when they were in their early teens. Doug Oakland went fishing every chance he could since that time, his mother added.
Mr. Oakland inherited Oakland’s from his father, who died in 1995. It was around that time that the he started utilizing the business to help his neighbors and community.
“And he always made sure they were successful,” added Mr. Glinka, referring to those groups and charities that hosted fundraisers at Mr. Oakland’s restaurant.
His death leaves a void that will not be easily filled, according to friends and survivors.
“It’s tragedy to everyone who knew him,” Ms. Capuano said. “He was way too young. They always say the good die young, right? It’s just so sad.”
In addition to his wife and mother, Mr. Oakland is survived by a brother, Gary, and four children, Doug Jr., 24, Briana, 22, Christian, 16, and Caroline, 14, as well as several nieces and nephews.
A wake was held for Mr. Oakland on Sunday and Monday at the R.J. O’Shea Funeral Home on Montauk Highway in Hampton Bays. A funeral was held on Tuesday morning at the Westhampton Presbyterian Church on Quiogue, and burial followed at the Southampton Cemetery.
Amanda Bernocco on Jul 7, 2015