Your first offshore race is a rite of passage that will provide wonderful memories for a sailing lifetime. Our friends at Sail Black Rock, Oakcliff Sailing, the Storm Trysail Foundation, and Gill have partnered with WindCheck to present our second annual youth essay contest, featuring a truly amazing prize!

The winning essay will appear in an upcoming issue of WindCheck (No, that’s not the prize!). The author will receive a very nice set of Gill foul weather gear and a berth for an offshore distance race on a turbocharged Farr 40 with Oakcliff coaches.

Oakcliff’s Farr 40s are among the best boats on which to learn how to race offshore. They provide an extremely modern and dynamic sail and deck plan to develop your sail trim skills on main, jib, and asymmetric spinnakers. Add to that Oakcliff’s highly trained professional coaches, and you’ll be on the fast track to becoming a qualified candidate for crew on the best race boats.

Official Contest Rules

•  “Why I Want to Push My Limits and Sail Offshore”


• This contest is open to U.S. residents ages 15 to 19 (inclusive) that have basic sailing experience and a desire to go offshore. Applicants must be able bodied and physically and mentally fit for the rigors of offshore racing.

Essay Structure

•   Essays must be original works of written art.
•   The maximum length is 700 words (excluding title & biography).
•   Please do not include applicant information on the essay page(s).
•   Please use 12-point Times New Roman font, double-spaced.
•   Please do not include graphics, special borders, colored fonts, or photos.


• Please list your name, grade, address, phone number, and email address.
• Include your sailing awards & achievements, school & community activities, and plans for college.
• Include your high school’s name, address, and phone number.
• Please limit your biography to one page.


• Entries must be submitted as PDF files, and attached to an email sent to The deadline is Saturday, May 9, 2020.


First-time offshore racers often they find that they are stronger than they thought; other times they learn more about their personal limits and how to manage them. Whatever the situation, the best offshore sailors push through for their crew. © Francis George/Oakcliff Sailing



Essays which meet the criteria above will be accepted and judged on the following:
• Creativity and clarity of thought
• Organization and topic content
• Grammar and spelling


• One Gill Race Fusion Jacket and one Gill Race Fusion Salopette in the winner’s size
• One berth on an Oakcliff Sailing Farr 40 Turbo for either the Ida Lewis Distance Race (August 14 & 15; or the Vineyard Race (September 4 – 6; with Oakcliff coaching


The winning essay will be published in WindCheck Magazine. Entrants agree that their essays may be published in WindCheck and on the WindCheck, Oakcliff Sailing, Storm Trysail Foundation, and Sail Black Rock websites.
By entering this contest, all participants agree that if their essay is chosen as the winner, it will become the property of WindCheck, Oakcliff Sailing, Storm Trysail Foundation, and Sail Black Rock. All participants further agree that the winning essay may not be submitted to any other contest or used for any other purpose.

About Sail Black Rock

Founded in 2011 and located at Captain’s Cove Seaport in Bridgeport, CT, Sail Black Rock is the home of the Fairfield University and Sacred Heart University sailing teams. Under the leadership of Program Director Dave White, Sail Black Rock hosted more than 700 visiting collegiate and scholastic sailors last year. Regattas include high school national qualifiers, intersectionals such as the Catholic Cup, intercollegiate performance ranking races; SHU National Trophy, Fairfield Cup, and the New England Freshman Championship for the Priddy Trophy. In addition to variant sea conditions of Long Island Sound, participants enjoy post-race pizza and ice cream parties sponsored by Sail Black Rock Foundation.


Oakcliff Sailing’s Farr 40 Turbos are an ideal platform for learning the art of offshore racing. © Francis George/Oakcliff Sailing


About Oakcliff Sailing’s Offshore Acorn Program

If you’re interested in learning to race offshore with Oakcliff, you don’t have to win this contest. You can apply for Oakcliff’s Offshore Acorn program from June 30 to July 19. Not only will you get coaching from Oakcliff’s highly qualified staff, but you will also get coached by Dawn Riley herself, veteran of four America’s Cup campaigns and two Whitbread Round the World Races (formerly known as the Volvo Ocean Race, now The Ocean Race). To apply, visit You can also email Training Program Director Ethan Johnson at to learn more about the program, financial aid, or other questions.

About the Storm Trysail Foundation

Based in Larchmont, NY, the Storm Trysail Foundation is a 501(c)(3) charitable organization dedicated to effecting, promoting and enhancing the education of young sailors; safe and knowledgeable transitioning from dinghy to big boat racing; safe boat handling in all conditions for all sailors; and safe blue water racing and passage making for all sailors. Chaired by offshore sailing legend Rich du Moulin, the Foundation supports a national program of events including Junior Safety-at-Sea Seminars, Hands-On Safety-at-Sea Seminars for adults and juniors alike, regattas including the Intercollegiate Offshore Regatta, and also through the making of grants to other institutions to foster similar education and training. Their latest initiative is support for the Collegiate Offshore Racing Circuit (COSC;, beginning with the acquisition of ten 33-foot Figaro2 ocean racers to seed a new intercollegiate sport: offshore racing. To learn more, visit


Want to put yourself in this picture? Submit the winning essay and you’re there! © Francis George/Oakcliff Sailing


About Gill

Founded in England in 1975, Gill is the world’s leading marine apparel brand. Their website states: “We are the optimists, bound by desire. The fearless, the gallant, the relentless. The ones bearing on obsessive, pushing through the pain to find glory.” To check out their complete range of technical clothing and accessories, log onto

About WindCheck

Described by a reader as “the best sailing magazine,”WindCheck is your source for Sailing the Northeast…and the journal of the best sailing community! WindCheck produces ten print editions annually, and with Publisher Ben Cesare at the helm we’ve launched a beautiful website that you’ll find at

Good Luck!