As the boats prepare for the start of the race, each crew has to be focused and listen to information flowing between the cockpit and the bow. The wind rips at your clothes, and a great wooden boat barrels towards you - tacking swiftly through the wind, the sails violently cross the deck. We navigate through tight quarters, attempting to slide into a better starting position without being blocked. We trim to sail fast as the timer gets to zero - right as we reach the start. The game is on.
Racing Classics
Oyster Bay has long been a sanctuary for sailing enthusiasts, where the rich maritime heritage and the spirit of competition come alive each year during the Classics Series. This prestigious event showcases a fleet of over a dozen exquisitely maintained vessels, each with its own unique story and historical significance. Maintained by the dedicated Stirling Harbor Foundation, these boats are more than just competitors; they are living pieces of nautical history.
The Fleet
Among these storied vessels are two classic Herreshoff designs, Dolphin and Mischief, known as "The Herreshoff Twins." Conceived in 1913 and launched on July 4, 1914, these Newport 29s met on a racecourse for the first time in over a century on August 18, 2019. Their reunion at the 47th Opera House Cup in Nantucket was a significant moment in the Classic Yacht Owners Association’s 2019 Classic Yachts Challenge Series. These identical twins, each 35’ 6” overall with over eight tons of displacement, are a testament to the enduring craftsmanship and innovative design of Nathanael Herreshoff.
Another notable participant is Chicane, a 56ft sloop designed by the legendary Scottish yacht designer Alfred Mylne. Built in 1926, Chicane’s restoration journey is a remarkable tale of dedication and passion. After being rescued from near oblivion by new owners Donn and Linda Costanzo, alongside a team of skilled craftsmen, Chicane emerged revitalized in 2020. Her triumphant return to racing in the Maine Classic Vintage Wooden Boat Races and her recognition as a finalist in the Classic Boat Awards 2021 highlight her storied legacy. Today, Chicane serves as the headquarters of the CI Bird Sanctuary in Oyster Bay, leading birding expeditions and continuing her legacy on the water.
The Classics Series is not just a race; it is a celebration of the art and science of wooden boat building, the thrill of competition, and the preservation of maritime history. For over a decade, SailAhead co-founders Sean and Kilian Duclay have been a part of this vibrant sailing community, collaborating with the Stirling Harbor Foundation and Oakcliff Sailing, a prominent sailing school in Oyster Bay. Join us as we explore the captivating stories and the enduring legacy of these magnificent vessels, and experience the timeless allure of the Classics Series in Oyster Bay.
Veterans Joining the Races
Since the fall of 2023 we have been using Shields 30s to go race with veterans against the rest of the classics. Occasionally, we win!
It's a thrilling experience for anybody to race on sailboats in such a beautiful bay. Races are intense, while also being welcoming enough for anybody with any level of experience to join in as a first timer.
Sailing in the beautiful Oyster Bay provides a wonderful escape from worries, particularly when facing the challenge of competing against the experienced sailors of Oyster Bay! We are part of a community committed to safeguarding the maritime history of the fleet, fostering a unique environment of particularly compassionate individuals. It is typical for other boats to jokingly tease us when we lag behind, or to encourage us as we overtake them towards the finish line!
Getting Involved
Do you want to get involved? Reach out! We are always welcoming more veterans and sailors who want to learn how to race, and be competitive on classic boats!
Veterans
Reach out to us to go sailing! Sailing is free almost any day of the week, with racing on Thursday and Friday afternoons. In our efforts to build a community of veteran sailors, we welcome any veteran with a willingness to learn about sailing.
Volunteers
Sailing experience is not essential, although it would be a great help! We are focusing on building a community of friendly sailors. The more the merrier!
Email us to start your journey!
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