The EESM, in collaboration with Shelter Island Yacht Club and the Stirling Harbor Foundation, is proud to introduce the Classic Boat Regatta which will take place on September 26th, 2026! The Race will take place in Gardiner’s Bay, near the EESM’s iconic Bug Lighthouse, with the start time and courses to be designated by the SIYC Race Committee and communicated at the Skipper’s Meeting on Race Day. For more information on rules, eligibility, scoring, and more, please visit our Notice of Race here. To register, please click below. Want to become a sponsor of the Regatta? Visit the Support Us page here, or reach us by email at jacob.raynor@eastendseaport.org.