Born in 1964, Dawn Riley grew up in Detroit, Michigan.^[1] Her parents were Chuck and Prudence Riley, and she was the eldest of three children. She began racing sailboats at age 13, and became Commodore of the Sea Scout program at the North Star Sail Club on Lake St. Clair. She also participated in track and field and is the Discus record holder at L’Anse Creuse High School.^[3]

In 1989-90, Riley joined the crew of Maiden, skippered by Tracy Edwards, which was the first all-women's boat to participate in the Whitbread Round the World sailboat race (now known as The Ocean Race).^[4] Riley was the watch captain, diver and engineer. They sailed a very competitive race, and gained significant media exposure, raising the visibility of women in the sport.^[5]

Riley then raced in the America’s Cup on the America³ team in 1992. She was the pit man in the Defender Series, becoming the first woman to have an active racing role aboard an America's Cup contender. Bill Koch was the skipper and patron of the team,^[6] which then went on to win the 1992 America's Cup.

The following year, Riley was the skipper of Heineken, an all-women's entry in the 1993-94 Whitbread race, the only all women's boat in the race.^[6] Riley flew in to Uruguay to take on the skipper duties after Nance Frank stepped down, following a dispute among the team members on the first leg of the race. She later wrote a book about the experience, entitled Taking the Helm.

For the 1995 America's Cup, Riley was the Team Captain for the all-women's team sailing on Mighty Mary, in the Defender Series. Mighty Mary, part of the America³ Syndicate, was sponsored by Bill Koch. Leading by a significant margin going into the last leg, Riley and the Mighty Mary team lost their wind, and Dennis Conner on Stars and Stripes was able to overtake them for the win in the final of the 1995 Citizen's Cup.^[7][8]

In 2000 Riley created and led America True, a coed team with a very modest budget that surprised all experts by outracing many of the top teams in individual races of the round robin and Semifinal competitions, including New York Yacht Club's entry and Dennis Conner's Stars & Stripes. The America True team had one of the 1st fully active foundations as a part of the campaign. The America True Foundation worked as a public foundation making sailing accessible with programs across the United States getting at-risk-kids out on the water. In 2021 it was folded into Oakcliff sailing and established a large scholarship fund specifically for graduates of the many community sailing programs that America True helped to create.

Riley served on the board of the Women's Sports Foundation from 1999–2006 , and as the President for 2003 and 2004. She is also politically active in the Democratic Party. She is a motivational speaker, and has traveled widely, speaking about leadership and team building.

In 2007 Riley continued to work in the America's Cup, as the General Manager of the French Team for the America's Cup, Areva Challenge. In 2010, Riley became the executive director of the Oakcliff Sailing Center. Oakcliff's mission is to improve the sport of sailing in the United States, and it operates out of Oyster Bay, New York with a fleet of nearly fifty racing boats, including the largest collection of Match 40s in the world.

• BMW Foundation Young Leader
• World Champion – 2003 One Ton Cup
• World Champion – Women's World Cup 1992
• US Rolex Yachtswoman of the Year 1999
• Michigan State University – Alumni of the year
• Michigander of the Year – 1999
• Inducted into the Michigan Sports Hall of Fame - 2023

• Dawn Riley at World Sailing
• America True
• Areva Challenge at the Wayback Machine (archived May 1, 2007)