Transforming sailing in Oyster Bay

The peaceful waters of Oyster Bay provide a picturesque location for sailing, which has attracted hundreds of trainees to the Oakcliff Sailing Center each summer since it opened in 2010.

“Oyster Bay is one of the most beautiful places to sail in and out of on the North Shore,” said Dawn Riley, Oakcliff’s executive director. “[It’s] green . . . peaceful and gorgeous and natural.”

With a fleet of just over 100 high-performance racing boats, Oakcliff trains and coaches sailors in preparation for major events like the America’s Cup, the Ocean Race and the Olympics. Named an official training center for the U.S. Sailing Team in 2013, Oakcliff is quickly achieving its goal of “raising the caliber” of U.S. sailing.

Oakcliff’s Oyster Bay location provides it with direct access to several local sailing ports and programs, including the WaterFront Center on West End Avenue, which offers sailing lessons for beginners and trains many of Oakcliff’s sailors.

“Oyster Bay has a wonderful variety of sailing venues between West Harbor, Cold Spring Harbor and the Long Island Sound,” Riley said. “You have [a] path from the WaterFront Center to here to become a professional sailor, but you also have two pretty good yacht clubs in Seawanhaka and Sagamore.” The Seawanhaka Corinthian Yacht Club and Sagamore Yacht Club are both in the hamlet.

Developing elite sailors each summer begins in November, when Oakcliff sends brochures to high schools, colleges and sailing programs across the country in search of recruits. Looking mostly for experienced high school or college students interested in careers in professional sailing, the staff starts each summer by preparing novice sailors for the strenuous training schedule ahead.

“We work really hard to inspire everybody to be the best they can, to perform with ethics, to be good, professional individuals [and to] work hard and give back,” Riley said.

As a non-profit organization, Oakcliff relies on donations from local and national donors to fund its facilities and activities, which Riley said slowly strengthened the center’s relationship with Oyster Bay.

“It took a little while because people still don’t know what we’re doing here,” Riley said. “They now know that it’s a good thing, but it was hard for the average person on the street to say what it was. But overall, we’ve put Oyster Bay on a lot of other people’s radars.”

Connor Sheridan, a Tufts University sophomore from Chicago training in Oakcliff’s summer-long Sapling Program, said its location and variety of programs have given him new experiences, like racing around Block Island, just off the coast of Long Island’s South Fork. Having only trained there for two weeks, Sheridan said he has already recognized the rich sailing culture that Oyster Bay has to offer.

“There’s obviously a really cool sailing community here [and] a lot of activity on the open sea,” he said. “I really like the East Coast.”

Veronica Lane, a college graduate from Copiague also training in the Sapling Program, works as a media intern for the center. Lane said in addition to writing newsletters and updating racing statistics, she has had many sailing opportunities due to the size of Oakcliff’s fleet.

“I sailed in college on 420s and [Flying Juniors], which are considered dinghy boats,” Lane said, “but here at Oakcliff, there’s so many different kinds of boats that talented people get to sail that I normally wouldn’t get the opportunity to experience.”

Sheridan said Oakcliff has also formed a relationship with local Oyster Bay businesses, who cater different events. Riley said local bars and restaurants, including Nino’s Pizza, Mario’s Pizzeria, Harborside Delicatessen and Carvel Ice Cream, have seen a “boon” to business from Oakcliff trainee visitation.

Along with gaining local traction, Riley said both the national and international sailing communities have noticed Oakcliff’s success, which she hopes will continue moving forward.

“Sometimes I think Oakcliff is the best kept secret in Oyster Bay, but around the world it is widely considered a magic training center,” Riley said. “We believe the future of the sport of sailing in America is being built here. Now we just have to get more local sailors on our beautiful bay.”