Friday, January 17, 2025
Dawn Riley’s life has always been connected to the water. From her early days sailing on the Great Lakes with her family to her groundbreaking achievements in competitive sailing, Riley’s journey is one of resilience, leadership, and a passion for community.
As the executive director of Oakcliff Sailing in Oyster Bay, she has dedicated the past 15 years to mentoring the next generation of sailors and fostering a deeper connection to the community, and the water making her the Herald 2024 Person of the Year.
Born in Michigan and raised near Detroit, Riley’s love for sailing began with a transformative family voyage when she was 12 years old.
“We sailed for a year on our cruising boat from the Great Lakes to Maine, Florida, the Bahamas, the Virgin Islands, Grenada and back,” the Bayville resident recalled. “It was critical to shaping who I am.”
That formative experience set the stage for a lifelong dedication to the sport.
In 1990, she was part of Maiden, the first all-women’s team to compete in the grueling Whitbread Round the World Race.
“The reason to do an all-women’s team is because the guys aren’t letting you, so you’re being shut out,” Riley said. “It’s just like in business. If you have all men on a company board it’s going to be a slow, difficult road for women to get in. As soon as you start getting three or four women in positions of power, then the floodgates open.”
The journey was chronicled in the acclaimed 2018 documentary “Maiden,” which followed the team’s tenacity and success.
Riley continued to blaze trails, becoming the first woman to compete in the America’s Cup in 1992 — and winning it. She then led an all-women’s America’s Cup team in 1995 and later served as CEO and team captain of America True, a co-ed team that competed in New Zealand in 2000. Riley also authored “Taking the Helm,” chronicling her experiences and insights into leadership and teamwork.
Despite these achievements, Riley emphasizes that her focus has always been on collaboration rather than exclusivity.
“Mixed teams in America are really the way to go,” Riley explained. “In most sailing, its equal and it’s just about skill.”
In 2007, Riley served as general manager for the French America’s Cup team, based in Valencia, Spain. She was at the height of her professional sailing career when she was approached to consult for the Waterfront Center in Oyster Bay. That project led to the creation of Oakcliff Sailing, a nonprofit organization dedicated to raising the caliber of sailing and sailors, and Riley found herself drawn to a new challenge.
“They used guilt to keep me here,” Riley jokingly explained. “I’d designed such a great program; they said I had to be the executive director.”
Though initially reluctant, Riley embraced the role, and Oakcliff has since become a cornerstone of the Oyster Bay community.
Under Riley’s leadership, Oakcliff Sailing has grown into a world-class training and resource center for aspiring sailors, from beginners to Olympic hopefuls. The center’s unique apprenticeship program provides participants with hands-on experience in sailing, boat maintenance, and leadership.
“Our mission is building American leaders through sailing,” Riley said. “It’s not just a sport. It’s about using all your senses, solving complex problems, and learning teamwork and resilience.”
Rich LaMarca, the Town of Oyster Bay’s clerk and Oyster Bay resident, highlighted the impact Riley’s work has had in drawing sailors to the community and working with other organizations like the Oyster Bay-East Norwich Chamber of Commerce, of which Oakcliff is a member, to further support the hamlet on and off the water.
“We’re very lucky to have a person as special and of her caliber in our community,” LaMarca said. “She’s an incredibly strong person, and while she likes to have fun, when it’s time to work no one works harder, and she leads by example.”
Riley was particularly proud of the center’s ability to adapt during the Covid-19 pandemic. By creating a self-contained bubble for participants, Oakcliff was able to continue its programs without any in-house cases of the virus. This resilience and ingenuity are hallmarks of Riley’s leadership style.
Beyond the water, Riley is deeply committed to the Oyster Bay community. She has collaborated with local organizations such as the Oyster Bay Main Street Association and the Chamber of Commerce, helping to grow events like the Holiday Market and the annual Water Lovers Mixer.
“We designed Oakcliff to fill gaps in the local sailing ecosystem,” she says. “We’ve always been about collaboration and giving back.”
Meredith Maus, executive director of the Main Street Association, highlighted the fact that before Riley took over running the holiday tree lighting, the event was a small and quaint affair. Over the years, it has ballooned into a hamlet-wide stroll and holiday market, featuring dancing, window decorating competitions, and greater participation from local businesses and vendors.
“It’s honestly just a pleasure to work with her, because you know that she cares about this community as much as you do and you know she’s going to bring her best to the scenario, so you want to show up in the same way,” Maus said. “She’s a total badass.”
Riley’s impact extends to young sailors at Oyster Bay High School, where Oakcliff’s program introduces students to competitive sailing and potential career paths in the marine industry.
“They’re learning more than just a sport,” she says. “They’re gaining job skills and life lessons.”
For Riley, the true joy of sailing lies in its complexity and inclusivity.
“Sailing challenges you on every level — physically, mentally, emotionally,” she says. “And it’s a sport where anyone can find a place, regardless of age or background.”
Members of Oakcliff’s team not only praised Riley for her incredible leadership and talent, but also for being an inspirational figure for young sailors. Siri Schantz, a boat captain and rigging manager at Oakcliff, explained that she came to the organization in part because of a desire to work with Riley.
“I had known about Dawn from a speech that she had given that I had been at years prior,” Schantz said. “So, I knew that she had all of this success with the Whitbread races and the Americas Cup, and I saw her as a hero for women in sailing.”
As she looks ahead, Riley is focused on continuing to expand Oakcliff’s reach and influence.
“We want to keep pushing boundaries and inspiring people,” she says. “Sailing teaches calculated risk-taking, problem-solving, and resilience — all skills that are invaluable in life.”
After 15 years at the helm of Oakcliff, Riley remains as passionate and driven as ever. Her journey from the Great Lakes to the international sailing stage and finally to Oyster Bay is a testament to the power of perseverance and vision. For her unparalleled contributions to the sport of sailing and the Oyster Bay community, she is a deserving choice for Person of the Year.
To learn more about Riley, Oakcliff Sailing, and the work they do, as well as to make donations, visit their website at OakcliffSailing.org.
