Second Annual Oakcliff Challenge Announced: Seeking Challengers

Second Annual Oakcliff Challenge Announced: Seeking Challengers


OYSTER BAY, NEW YORK (February 17, 2016) – On June 3rd, Oakcliff Sailing will host the second annual Oakcliff Challenge. On Oakcliff’s fleet of Swedish Match 40s, the event will include an onsite coaching clinic, a day of fleet racing, and a day of match racing.

Competitors will arrive on Friday for a clinic with coaching from David Dellenbaugh.

Dellenbaugh is the publisher, editor and author of Speed & Smarts racing newsletter. He was the tactician and starting helmsman on America3 during her successful defense of the America’s Cup in 1992 and sailed in three other America’s Cup campaigns. David is also a Lightning world champion, two-time Congressional Cup winner, seven-time Thistle national champion, two-time winner of the Canada’s Cup match racing championship, three-time Prince of Wales U.S. match racing champion and past winner of the U.S. team racing championships for the Hinman Trophy. He coached the US match racing team at the 2012 Olympics, and is currently a tactical and rules coach for the US Sailing Team during its run-up to the Rio 2016 Olympics.

Saturday will be a day of short course fleet racing with on-the-water, real-time coaching. Sunday will be an official ISAF grade 5 match race regatta. Each day will conclude with a post-race debrief led by Dellenbaugh and Oakcliff coaching staff. A champion will be crowned for fleet racing, match racing, and overall winner.

Included in the entry fee is onsite housing at Oakcliff’s recently renovated loft-style bunkhouse. On Saturday night, competitors will gather and enjoy dinner and refreshments.

“I’m not sure of any other event in the country where you show up with your team and find beds to sleep in, world class coaches, fleet racing, match racing, and a party to end the night,” says Race Program Director Bill Simon. “Grab your friends, make a team, and get over here – you won’t regret it.”

This unique, multi-format racing event encourages those new to match racing to get first-hand experience on premier boats. The event was conceived in response to discussion and increased demand for greater variety in the sailing calendar. Yacht clubs, college teams, and sailing centers are all invited to attend.

There is no charge to request an invitation. Total entry fee is $850 which includes onsite housing and Saturday night dinner. Teams not staying in the Bunkhouse recieve a $100 discounted entry fee.

For more information or to request an invitation, click here.

Oakcliff Sailing is a non-profit coaching and training center for sailors who have progressed beyond traditional coaching methods. The center can be contacted by email at or by calling (516) 802-0368.

For more information: 
Scott Guinn
Director of Public Relations
Oakcliff Sailing
(845) 664-8012