News

Mark your calendars for this year’s Doublehanded Offshore Race on July 14-15. The race will be held in modified Melges 24s and continuously live streamed for 24+ hours, allowing spectators to watch every step of the way.  Last year’s groundbreaking event demonstrated that doublehanded offshore sailing...

June 20, 2020 (OYSTER BAY, NEW YORK) – The five teams that raced Match 40s in Oakcliff’s June Grade 5 Regatta were served a mixed bag of conditions. The regatta started in a shifty 4 knot Northerly that swung and built to a gusty 10-12...

June 7, 2020 (OYSTER BAY, NEW YORK) - The Oakcliff Quaranteam Regatta had a slow startwith hot and glassy conditions but the Match 40s jolted to life when a thunderhead rolledthrough bringing rain and 16 knots gusting 20 with 30 degree wind oscillations. Out of...

While countless people are breaking out their lederhosens to celebrate Oktoberfest, Oakcliff is bringing in a mechanical bull to the party...

Oakcliff Training Program Director, Ethan Johnson, and Cat Chimney, Technical Specialist & Rigger, traveled to Ethan’s stomping grounds, the Old Line State of Maryland, to compete in the 2019 Annapolis Yacht Club Double-Handed Distance Race. With the support of their sponsor, CFOforaday, they entered in...

The 2019 Vineyard Race hosted by Stamford Yacht Club started in 15 knots of breeze gusting 18 with sunny skies. It was a downwind run off the line and all three Farr 40s deployed their A2s. They each also set a staysail for extra stability and a little...

Join Oakcliff for a once in a lifetime opportunity to meander through a private and beautifully restored meadow on Centre Island. Along the way discover art  placed just for this event and enjoy light refreshments. Learn more about the show and buy your ticket here 2019...

Exercising at Peak 180 when he was still at Oakcliff Last October, Oakcliff collaborated with New York Yacht Club American Magic, Challenger for the 36th America’s Cup, to host a week of training & tryouts with Oakcliff graduates. Sean O’Halloran stood out amongst the candidates.  When...

 A little over a year ago, Sara Stone left her career in infectious disease control to become a Sapling at Oakcliff and pursue her dream of doing the Ocean Race. Since graduating from the program, her career has been pedal to the metal; just last week she did bow...