Creating new beginnings in Oyster Bay

Published on December 19th, 2021

Oakcliff Sailing does it their way, but if you’ve ever met Executive Director Dawn Riley, you knew that already. Founded in 2010 to raise the caliber of sailing in the United States, Oakcliff Sailing has touched every sector of the sport from its base on the North Shore of Long Island in Oyster Bay, NY. Here’s an update from 2021 National Hall of Fame inductee Riley:


Oakcliff has been building American Leaders for over a decade; almost 400 leaders built and counting! It is always challenging, often fun, definitely high energy, and each day trains both the trainees and the coaches to be just a little bit better.

So, when we faced one of the biggest challenges yet, we tacked immediately, created our own bubble and sailed through the pandemic with creative solutions. I don’t think most of us realized just how lucky we were until we started traveling during the summer of 2021.

And travel we did! Offshore sailors spent 10 days training on the water with Training Program Director, Ethan Johnson. When the Block Island Race was canceled, our teams headed out into the eye of the storm to get real world, full on, but relatively safe heavy-weather sailing.

After this training, we headed to Annapolis and Newport, and the wind Gods paid us back – downwind, champagne sailing for 400 miles and a 2nd place finish!

July saw the team take on our biggest boat yet – OC 86 – donated by the DeVos family, with a little bit of trepidation, I’m sure. With the help of some select professionals, we trained for a week in beautiful Western Michigan and then raced the Chicago Mackinac, where the biggest danger was a moth infestation.

When we reached the island there were hugs all around, with fellow competitors quite amazed that a boat of young and somewhat small sailors had just grabbed line honors. To be fair the media did feature the biceps of our grinding team, featuring Anna Sems, who weighs in at a whole 94 pounds.

The Bayview Mac saw us a bit more confident, with a pretty amazing weather forecast; if we could just do everything right. The day had an inauspicious beginning as we ran smack aground, on the Canadian side, as the rest of the fleet passed us by. Time to reboot. We had a team meeting, admitted to a team brain fart (bet you have never seen that word in a year-end letter before) and restarted.

With attention to navigational details by Ethan and Brad Farrand and some world-class sail calls from the bow, we snuck through a front between a tornado and a dismasting. The wind fairies kept us moving with gentle lifts and following seas to finish at a combined sunrise and moonset; 3rd in class, 3rd overall and the fastest monohull on the shore course, ever!

This means that Oakcliff teams, made up entirely of coaches and trainees, now hold two course records: The Around Long Island Race in the Judel/Vrolijk 66 Numbers and the Mackinac Shore Course in the Reichel/Pugh OC 86. Of course, this couldn’t have been done without hard-working and dedicated trainees. More importantly, it couldn’t and can’t, be done without generous supporters. We invite you to join us as a supporter as we head into a new, fresh and clean season.

At my induction to the National Sailing Hall of Fame, I used my three minutes on the podium to plead with the audience to help us bring more gender equity, more diversity, and more great individuals into our sport.

To that end we have rolled the America True Foundation into Oakcliff. We now have a fund of just over $150,000 reserved for scholarships, specifically for aspiring world-class humans from community sailing programs who would like to train at Oakcliff.

You can ask that your donation be directed to that fund, or you can help us identify, mentor and sponsor a young person for the Oakcliff programs. And as always, donations for general purposes are very welcome.

As we all go forward, we are looking towards having you as part of our team, creating new beginnings for yourself, your family and friends, as well as those friends you haven’t even met yet.

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