The Stirling Harbor Foundation is proud to join the East End Seaport Museum and Shelter Island Yacht Club for the inaugural Classic Boat Regatta on September 26, 2026.

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The regatta will take place in Gardiner’s Bay near the East End Seaport Museum’s iconic Bug Lighthouse. The start time and race courses will be determined by the Shelter Island Yacht Club Race Committee and announced at the Skipper’s Meeting on race day.

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During the Greenport Maritime Festival, SHF will also have a booth where visitors can meet our team, learn more about our programs, and find out how to get involved.

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The Classic Boat Regatta will bring together a fleet of classic vessels for a day of racing, camaraderie, and celebration on the water. We look forward to being part of this exciting new event!

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For information on rules, eligibility, scoring, and registration, please contact the East End Seaport Museum at director@eastendseaport.org.