“There is no other place in America that does more for building talent, our sport and industry,” said Dawn Riley, executive director of Oakcliff Sailing.
That place – Oyster Bay – is the home of one of the nation’s largest sailing training centers. Oakcliff opened its doors in 2010 and has since graduated nearly 1,000 sailors through its programs. The coaching and training center helps experienced sailors ages 15 and above through a variety of programs and courses that set them up for future success in the sport and industry.
Riley was invited to Long Island in 2009 to do a consulting project on what was needed to provide sailing instruction on the North Shore. Afterward, she was invited to run the Oakcliff Training Center, a position that she still holds.
Riley is one of the most decorated sailors in the world herself. She was the first American to sail in four America’s Cups and two Whitbread Round the World races, and she was also the first woman ever to manage an entire America’s Cup syndicate.
Riley is a member of the International America’s Cup Hall of Fame, the National Sailing Hall of Fame, and the State of Michigan Hall of Fame.
Graduates and trainees of the center have also earned several distinguishments.
Oakcliff alumni have won The Ocean Race, while trainees and coaches have won the Herman Hawkins and Youth Trophy in the 2024 Newport to Bermuda race, the Miami to Havana Race, the NYYC Annual Regatta, and the Opera House Cup. Oakcliff sailors have also finished on the podium for Bermuda, Around Block Island, and Vineyard races.
Teams made up entirely of Oakcliff members also hold course records for The Around Long Island Race, set in 2018, and the Bayview Mackinac Shore Course, set in 2021.
But how has a sailing center so young prospered into one of the top programs in the country?
The center has eight full-time staffers, along with multiple volunteers who help teach the next generation of sailors.
Oakcliff has roughly 100 boats that are used regularly and offer a variety of classes. The center has both winter and summer programs, ranging in length and price. Tuition prices for the programs include room and board as well.
Oakcliff also provides sailors the opportunity to compete in many offshore races. One of those races includes the Newport Bermuda Race, one of the more well-known competitions in the sailing community.
And when asked if the training center was one of the largest of its kind in the country, Riley wasn’t shy to share the Oakcliff’s prestige.
“You could argue in the world,” she said.
Oakcliff provides an updated calendar on its website that highlights upcoming events and races. That includes the 2024-25 Celebration and Collaboration Tour that will see graduates and current members of the center meet up across the United States.
