When Dawn Riley was serving as the 14 year-old Commodore of the Junior Yacht Club of the North Star Sail Club in Michigan, she declared that she was going to sail in the America’s Cup and race around the world one day. She has achieved her early dreams and gone beyond as a competitive racer, champion of women in sailing and teacher to many aspiring young sailors. In her autobiography written with Cynthia Goss, “Taking the Helm,” she makes a strong case that women can be equally competitive with men in offshore sailing. She has raced around the world twice – first aboard Maiden in the 1989-90 Whitbread Round the World Race and then as skipper of Heineken in the 1993-94 edition of the Whitbread. In between races she joined Bill Koch’s America3 campaign as a crew member. The team successfully defended the America’s Cup in 1992. Riley was the only female member of the sailing team.

Riley joined the all-women’s crew aboard Mighty Mary for the 1995 America’s Cup and used the experiences she learned during both campaigns to launch her own Cup challenge, America True in 2000. She was the captain of the team that made the semi-final round. In 1999 Riley was named Rolex Yachtswoman of the Year for her victories on the match racing circuit. She is a graduate of Michigan State University and was on the sailing team. Riley has served on many Boards, including the Women’s Sports Foundation (1999-2006). She served as President of the Foundation in 2003-2004. Riley has also served on the Board of the US Sailing Association, the governing body of sailing in the United States.

Riley managed the French “Areva Challenge” for the 2007 America’s Cup in Valencia, Spain. In 2010, she was hired by Hunt Lawrence to run Oakcliff Sailing in Oyster Bay, New York. Oakcliff has a mission to train sailors in the skills of offshore sailing, match racing and Olympic sailing preparation. She is an advocate of mixed sailing (men and women on the same boat) and says “I’ve seen an all-male crew because I’ve been the only woman on the team, and I’ve been on mixed teams. I love mixed teams. The dynamic is different, but it is a more complete team. You’ve got enough different perspectives that you have better decision making capability.”

In 2019, a feature film on the 1989-90 Whitbread Race, “Maiden” told the story of Riley and the rest of the resourceful crew and their quest to prove that women can compete in blue water racing. She recalls “We started the race and many people thought we were going to lose and cry and all that kind of stuff and we won two of the hardest legs with all women aboard. When you are away from land and there are only ten people on the boat, it doesn’t matter if they are male or female. There are absolutely no jobs women can’t do offshore.” She continues, “In my opinion, the last frontier for women in sailing is in decision making roles. Women in leadership with decision making powers is where we need to go. The next step is for more women to own their own boats.”

~ Gary Jobson