Dawn Riley: Looking back, Looking forward

Published on December 16th, 2022

With a sport like sailing, having an opportunity to participate is not as simple as other recreational options. Helping to improve the odds is Dawn Riley at Oakcliff Sailing in Oyster Bay, NY. Here is her year end update:


In June, I was standing on a busy corner of Thames Street in Newport (RI) and waved hello to a graduate. My view widened and I realized there were graduates on all four corners of the intersection. At this point, one shouted out, “We’re everywhere boss!” Funny, but also true.

It is hard to see any program without graduates from the America’s Cup, to The Ocean Race, to the Olympic Development Teams, to the Women and Youth America’s Cup teams, to the Caribbean Circuit. They are at trade shows, conferences, and on coaching staffs. I even received a video of a guy wearing an Oakcliff shirt walking through a bar in Argentina.

It’s hard to go anywhere in sailing without seeing Oakcliff’s effect. The 2022 Newport Bermuda Race was the first time in 12 years where our Offshore programming was completely full. Seventy-nine people on five boats headed out and 28 joined in for the return.

The Bitter End Yacht Club Team was comprised of nine high school girls and two coaches, who trained all spring and raced Oakcliff Farr 40 Blue to Bermuda. A little more-old school (my generation), Maiden spent almost two weeks in Oyster Bay, and the permanent crew was blown away by all of the activity.

Sail GP

Our World Match Race Tour Academy consisted of nine women and two men. Mixed+ is a growing phenomenon in sailing, which is where 50% or more of each team must be female. At Oakcliff we are Mixed+ on any given day.

We continue to use all of our resources as efficiently and respectfully as possible, including the environment. Our partner, 11th Hour Racing, led by graduates, are now circling back and helping us develop a sustainability toolbox. We’ll once again be supporting them by sending team members to the stopovers.

As momentum continues to build, we continue to provide unique opportunities.

Our biggest push is to expand the diversity of our programming by doing more outreach with Community Sailing Programs and provide scholarships through the America True fund. We also continue to help the High-Performance Olympic hopefuls from varied backgrounds and build our local community footprint with High School Big Boat sailing.

On the big-boat front, we will continue with OC86. The DeVos Family generously donated this boat and helped us keep it going. Sponsors, including Redkik, added to that support. OC86 is for sale, but we would like to keep the program going.

There is literally no other place that a person who isn’t an owner or a “pro-pro” can get experience on a massive boat like the OC86. Remember Safe Harbor Race Weekend where we raced with 29 instead of the normal 19? The sailors were small and young and we won the first day of racing. Invaluable!

As we look back, we are also looking forward and asking you for three things:

• Consider making a donation to help us in our work and become a 2023 supporter or to support a specific program.

• Continue to spread the word about Oakcliff to other possible supporters and donors.

• Help us reach out to the next generations of athletes. You know them, you know Oakcliff, you are a valuable asset who can help find and support the next rockstar of sailing, the next leader of people, the next American woman to race in the Jules Verne… or that would be the 1st.

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