Construction on Bunkrooms Has Begun!




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After a lot of planning we are finally in construction to build dorms upstairs for Acorns and Saplings and visiting sailors. We have had one individual who has agreed to donate 20% of construction costs and we have our very first bunk sponsor. Call us at 516 802 0368 or email to learn more about getting your name on a bunk a room or even a shower stall!

Art Show A Beautiful Success

The skies cleared,  the sun came out and the artwork sparkled at Oakcliff’s second annual Spring Art Show. The event is the brainchild of founder Betsy Lawrence who not only curated the show but also participated as an artist as well. This year’s theme was the Intersecting Circles of Oakcliff, Oyster Bay and the Olympics. Even the catering was all about circles and the letter “O”. James Muir of Artaux Catering presented a menu including: Omelets, Olympic blueberry pancakes, Octopus in a soba noodle salad, Orzo salad with feta, Olives and sun dried tomatoes, tiny circles of caviar on blinis, and finally a rum soaked mount Olympus cake. The Artists, who all donated some if not all of the proceeds to Oakcliff were the real stars of the show. Scroll down to see the artists with their work.  All artists can be reached by sending a request to A big shout out to Sonja Drabin for being a charming hostess and to Andrea Watson for stepping up to be the official photographer.  Her photographs can be seen here.  Also thank you to Oakcliff staff who brought their “A-Game” in cleaning and polishing and giving tours of the facilities, including the soon to be constructed Sailors Bunkhouse.  Finally to everyone who came and enjoyed and purchased and donated.  Thank You!

Betsy Sails Circling

Betsy Lawrence with Sails Circling, Oil on Canvas (not for sale)

Betsy Sculpture

Betsy Lawrence with her Bronze of “Pan” the God of Nature 6″x9″
Available: $1000

Yana Copek

Yana Copek Photographs
Most Available: $125

Richard Bonomo

Richard Bonomo “Women on the Beach”
Oil on Canvas 16×20
Available: $8000

Jeff Truelove

Jeff Truelove “Liminal Place” Wood, Ink, Varnish
Not Available … Yet

Youngmi Kim

Youngmi Kim
“Untitled” Mixed Media 30 x 40 – Sold
“Monologue” (not pictured) 20 x 16 – Available $800

Windy Noviardy

Windy Noviardy “The Wanderer”
Mono-print: Chine Colle
Available: $625

Teresa Waterman

Teresa Waterman “Caught in Contemplation #2″
Mixed Media, acrylic, Graphite, and Pastel. 35 x 24
Available: $2500

Taube Rothman

Taube Rothman “Spinning”
Acrylic on Foamboard

Nancy Shapiro

Nancy Shapiro “Encircle”
Available $2500

Judie Swanson

Judie Swanson “Breath of Light”
Oil on Canvas 36 x 36
Available $1850

Mary Mattingly

Mary Mattingly “Untitled”
En-caustic and Mixed Media 9 x 9

Liz Roosevelt

Liz Roosevelt
Over Sold

Kirk Larson

Krik Larson “Learning to Fly”
oil on canvas 16” x 20”
Available $2200



John Taylor

John Taylor “America’s Cup Trials – 1901″
Oil on Canvas
Commissions Available

Henery Finkelstein

Henry Finkelstein
Oil on Canvas 40 x 48

Diane Schottenstein

Diane Schottenstein “Sails on Oyster Bay”
Watercolor Paint

Dennis Bourke

Dennis Bourke “Six Circles”

Caryl Stern "Emergence" and "Abundance" Oil on Canvas Emergence (top) Available $2000 Abundance Sold

Caryl Stern “Emergence” and “Abundance”
Oil on Canvas
Emergence (top) Available $2000
Abundance Sold

Carl Copek "Circles" Color Metallic Print Available $125

Carl Copek Circles
Color Metallic Print
Available $125


Ayumi Shibata "Deep in the Water Series: Coral, Flow, Blue Tale" Etching Prints (20 Layers) and Hand-Cutout Available $1500 to $2500

Ayumi Shibata “Deep in the Water Series: Coral and Flow”
Etching Prints (20 Layers) and Hand-Cutout
Available $1500 to $2500

A Reminder to Thank Your Race Committee

Coach Jay Kehoe aka Pin Boat Operator reports from Miami

Yesterday was a hot and light day, we got out at 9:30 on the course and got done at sunset! Pretty long day for sure with only one race in each class!

Today, we were greeted with RAIN and no wind! Again we got out to the course at 9:30 or so but today due to the big storms rolling in we were able to get in early!

Big lesson for me so far is how much of an effort this event is to put on! With 6 race circles (most with Trapezoid course configuration), multiple mark boats, International Jury and onshore support people it is out of control, wait I forgot Swiss timing, this is the new tracking system that ISAF wants to use, quite honestly it is not very Swiss as we on the pin boat have been lost more races than we have been found. I think once the bugs are worked out it will be pretty awesome but it does take one if not two people on the signal boat to work it!


The other lesson is how far a THANKS goes! I try and say thank you when I can to the RC, but after helping here, it is now a requirement! As a sailor or coach you do pretty much the same thing these guys do, wake up, check weather, eat breakfast and talk about the day with your team, check e-mail, look at weather again, leave for the site, ready your boat (for mark boats it is put on tracker, check fuel, add trackers to the marks and make sure the plugs are in the marks and check email, weather etc.)

Then it is time to get out on the water, check wind (or lack there of), check current, set marks… reset marks and set up start line and go racing. The other thing most people fail to think of is how would I sail this course, how can I keep everybody from bunching up on one end of the line?

We are using some cool tools here, a range finder will now be part of my RC kit, the “U” flag, this is a black flag without the penalty if there is a general recall, it works.

I am psyched to be down here and learning it is a good thing for sure.

Off to another quick meeting with some people who want to learn about Oakcliff.

Oakcliff All American Offshore Team Alumni to Sail Around the World

Oakcliff AAOT Brain Trust- Photo Credit Amory Ross

Oakcliff AAOT Brain Trust- Photo Credit Amory Ross

January 29, 2014

Oakcliff Sailing – Oyster Bay NY: Congratulations to the core of the Oakcliff All American Offshore Team who have just announced that they are also the core of the Turkish backed Volvo Ocean Race Team. Charlie Enright and Mark Towill have been confirmed and they are working quickly to put together the rest of the team who will also be under 30. The official announcement will be made Friday at 3am EST.

Oakcliff will be chatting with Charlie and Mark when they return to the United States next week. Part of that conversation will be with another group of Oakcliff SapGrads who are busy planning a 2015 campaign for the Transatlantic Ocean Race and the Atlantic Ocean Racing Series. Charlie and Mark led the Oakcliff AAOT team that was supported Oakcliff and USMMA-SF in the same series of races.

Oakcliff Sailing has been building American Leaders through sailing for 4 short years. One of its many long-term goals was to have graduates in the America’s Cup and the Volvo. SapGrad Solomon Krevans raced in the Red Bull Youth America’s Cup and now there are Oakcliff sailors headed to the Volvo.

Executive Director Dawn Riley comments, “I always say set your goals very high, anything less is just a ‘to-do list’. Well we set our goals very high and Oakcliff Graduates are conquering! Congratulations Team!”

Oakcliff is the only comprehensive training and coaching center in the world. Oakcliff’s signature Sapling and Acorn programs produce graduates who are complete sailors capable of sailing in any position, fixing every aspect of a boat and managing a business.

NOTE: Applications are currently being taken for the 2014 Acorn and Sapling program

Oakcliff is a non-profit organization open to sailors of all ages and levels. Oakcliff’s rigorous curriculum trains sailors in match and fleet racing, inshore and offshore, fully crewed and short handed as well as providing access to historically significant classic yachts. Oakcliff was also named the first US Sailing Team Sperry Top-Sider Training center with 8 of each of the Olympic Classes: Nacra 17, 49er and 49er FX.

Jay Complains of the Heat

Seriously? Jay is complaining that it is too hot? Everyone get your tiny violins ready and read his report from yesterday:

Long Day on the water yesterday. Started with the 7:45 coaches meeting and ended at 8 pm with a redress hearing!

I thought coaching was tough but being on Race Committee as the pin race officer is exhausting. Our line is between 325 and 400 meters. As a point of reference, Division 1 at Key West with the TP 52s was only 200 meters. It is a long line and the boats use a lot of it.

It is really exciting racing with 34 boats with wings jockeying for a spot on the line. On top of this, it is a relatively short course so they are compacted and all going around the bottom mark within seconds.

Oakcliff Supporters pointing out Oakcliff is Too Good to be True in Miami

Oakcliff Supporter Sam Murray pointing out Oakcliff is Too Good to be True, in Miami

As the pin boat we not only set the line, we have to deal with gates as well and then book it over to set up a finish line. The day flys by!

A bonus is that in the mornings at the hotel I get to talk about Oakcliff with sailors from all over the world. This morning in particular, I spoke to a team from Singapore as well as one of the top US juniors. They are all excited to sign up for this summer’s Acorn and Sapling programs

On the course for day 2 unfortunately light and hot.

Jay off!

ISAF World Cup – Oakcliff Making it Happen

Program Director Jay Kehoe reporting:


Team Funky-Bird Practicing in an Oakcliff Boat

Good Evening from Miami!

Will not tell you how nice the weather is for you northern folks, but it is really nice!

I am at the Rolex Miami Olympic Classes regatta the first ISAF World Cup event for 2014 and the only one in North America. I am down spreading the word about Oakcliff and our programs, I am also on the Pin boat for the 49er and FX course. It is going to be exciting with 35 49ers and 35 Fx’s on the line, the racing will be epic. A big reason the fleets are so big (the largest at a World Cup event) is because of infusion of Oakcliff boats that are here for members of the US team. The impact that Oakcliff is making is pretty impressive.

Last night I was fortunate enough to be invited to the US Sailing Team Sperry Top-Sider awards ceremony, it was truly amazing having so many sailors come up to me and thank me for what we are doing at Oakcliff. During the awards Hunt and Betsy Lawrence were presented with the Charles M. Leighton Award for outstanding dedication to the U.S. Olympic sailing effort, during the presentation team members were asked to say a few words about Oakcliff. It was amazing and very inspiring! The US team is doing great things and Oakcliff is a HUGE part of that and the athletes are very grateful. Thanks Hunt and Betsy your efforts are going to see results!

Today was a very busy day getting the course boats ready, with 6 race circles and 3-4 mark boats per course it is pretty hectic getting all the marks, flags, whiteboards and support boats ready for the upcoming week of racing. The US Sailing Staff with volunteer help does a great job organizing your kit beforehand but there are always a few bits missing and you have to go on the hunt. Being the first time on RC down here I was tasked with finding all the missing parts so I had a long day walking and looking. All seems put together right now and looks like we are ready for racing starting Monday.

Tonight is the opening ceremony, with all the countries being recognized and a good way to kick off the racing for the week. Weather forecast looks light for the first few days then big breeze by mid week!

Stay tuned for some pictures of racing tomorrow and another report of how the day turned out



Advancing American Sailing This Holiday Season!

The United States successfully defended the America’s Cup with only one American on board.
Do you have a nagging sense that the greatest comeback in sports history was not entirely ours?

Oakcliff foresaw this travesty and created a solution. We are working hard to rebuild and change the face of American Sailing as well as the lives of all who pass through our doors. It is working!

In 2013 Oakcliff:
Became the first official US Sailing Team Sperry Top-Sider Training Center
Expanded our fleet to include the world’s largest collection of Olympic class Nacra17s, 49ers, and 49er FXs
Hosted more match racing than any other sailing center in the country
Organized and hosted 19 regattas including the NACRA17/49er/49erFX US National Championship and the Oakcliff International
Celebrated 13 podium finishes for our Offshore Teams
Sent competitors to Grand Prix events including the Mini Transat, Red Bull Youth America’s Cup, Grand Slam Match Race Series, and Farr 40 Worlds

We have done this with a small, dedicated group of donors, supporters, and volunteers contributing their time and dollars. We ask you to join this special group and help keep the wave of change rolling.

We are doubling our training programs in 2014. For the first time, we are adding an Adult Acorn program where adults can see how they stack up against the young pros. We will also offer a high performance dinghy camp aboard our 24 brand new Olympic class skiffs and multihulls. This influx of new trainees needs your support to reach their full potential. They also need a place to stay. To that end we will be building more housing. Your tax-deductible gift ensures Oakcliff will continue to lead America in regaining our dominant position in International sailing.
Everything happening at Oakcliff seems almost too good to be true…but it’s real. Best yet, as a supporter you get to join and sail with us. Your donation of $500 or more will be applied directly to equipment and programming:
$2500 will buy a sail
$5000 will scholarship an Acorn
$100,000 will underwrite an offshore campaign

You can send in your support by mail or by visiting
If you would prefer to customize your gift we would love to set up a time to speak in person or by telephone. Call us at 516-802-0368 or email Please join us and support this unique program that changes lives and advances our sport.


Dawn and the Oakcliff Sailing Team