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.

To view our Notice of Race, please click here.

All registrants must be eligible as defined in the NOR section 3, which has been reproduced below. The NOR is available in its entirety in the dropdown menu above or can be found here:

ELIGIBILITY and DIVISIONS

3.1 Following the Classic Yacht Owners Association’s Classic Race Formula (CRF) guidelines for classic yacht divisions and ratings (https://www.classicyachts.org/ratings/), the Bug Light Classic Regatta will offer racing divisions for:

(a.) Vintage boats designed prior to January 1, 1950. And built, maintained and restored with materials and methods reasonably consistent with the original design.

(b) Classic boats designed on or after January 1, 1950 whose rudders are attached to the trailing edge of the keel. (c.) Modern Classic boats designed after January 1, 1950 and typically before January 1975, whose rudders are separated from the keel.

(d.) Spirit of Tradition boats designed on or after January 1, 1975 and whose rudders are separated from the trailing edge of the keel and whose design embodies an appreciation of classic yacht or traditional workboat shapes and aesthetics.

3.2 Spinnakers: Any entry may sail with a Spinnaker under their CRF 2026 rating.

3.3 A CRF 2026 rating certificate is required for all yachts. The application form can be downloaded from http://www.classicyachts.org/ratings/certificates/. Please do this as soon as possible, as it may take several days to get a CRF rating.

Entry Fee: $150

Registration forms accompanied by an entry fee will be accepted through September 1st. For any registrations made after September 1st, $25 is added to the fee. Registration includes entry to the Race for one boat (compliant with the rules of the Race) and two tickets to the afterparty held at the Museum. All registrants must attend a mandatory skipper’s meeting at the East End Seaport Museum on race day at 0900.

As the Regatta will be taking place the same weekend of the annual Maritime Festival, the Museum recommends parking in the Long Island Rail Road parking lot off of Fourth Street to the South of the Museum, or parking on Shelter Island and taking the ferry by foot.