Bug Light Classic Regatta revives Greenport sailing tradition
A classic sailing tradition is returning to Greenport Harbor this fall after more than a decade.
The first Bug Light Classic Regatta will be held Sept. 26, reviving the former Greenport Classic Yacht Race, which was last held in 2012.
The regatta — hosted by the East End Seaport Museum, Stirling Harbor Foundation and Shelter Island Yacht Club — coincides with the 36th annual Maritime Festival.
“More than just a race, the event will anchor a true maritime weekend in Greenport — a celebration of the working harbor, the craftsmanship of classic yachts, and the living maritime culture that has defined this village for generations,” the museum said in a release.
Classic yacht owners and sailors from across the East End are expected to take part in the race, which the museum hopes will become a regular stop on the Classic Yacht Owners Association circuit.

Following the competition, the celebration will move ashore for the “Rum and Reggae After Party” at the museum, featuring live reggae music, rum-based cocktails, waterfront appetizers and an awards ceremony recognizing the top finishers in each division.
“It’s a fitting close to the day — trading the discipline of the race course for an easy, festive toast to the boats, the builders, and the harbor that brought them all together,” the museum said.
The regatta comes as the East End Seaport Museum steps back from organizing the Maritime Festival itself. The museum ran the village tradition for 35 years before announcing last fall that it would no longer lead the event.
The Greenport Business Owners Alliance has taken over stewardship of this year’s festival, while the museum remains involved in maritime programming of its own.
Tickets are $75 and all proceeds benefit the East End Seaport Museum.

