The East End Seaport Museum is bringing a classic yacht racing tradition back to Greenport Harbor this fall with the inaugural Bug Light Classic Regatta, set for Saturday, Sept. 26, during the village’s annual Maritime Festival weekend.
Organized by the East End Seaport Museum and Stirling Harbor Foundation, with support from the Shelter Island Yacht Club, the regatta will send classic sailing yachts into Greenport Harbor and Gardiner’s Bay for a day of racing within sight of Long Beach Bar Lighthouse — better known locally as Bug Light.
The event is a revival and reimagining of the Greenport Classic Yacht Race, a community sailing tradition last held in 2012. Organizers hope to draw classic yacht owners and sailing enthusiasts from Shelter Island, Sag Harbor and elsewhere across the East End.
The new regatta is also intended to highlight Greenport’s long connection to boatbuilding and the working waterfront.
For more than a century, Greenport’s shipyards and waterfront shops built and repaired fishing boats, oyster boats and sailing vessels. Although the industry has changed dramatically over the decades, wooden boatbuilding and restoration remain part of the village’s maritime culture.
Organizers said they hope the Bug Light Classic will eventually become a regular stop on the Classic Yacht Owners Association race circuit, joining established classic yacht regattas held elsewhere in the region. The event was inspired in part by the Herreshoff Marine Museum’s annual Herreshoff Classic Yacht Regatta in Bristol, R.I.
The race will also become part of the broader Maritime Festival weekend, which each September draws thousands of visitors to Greenport for events celebrating the village’s nautical history and waterfront.
Following the racing, the festivities will move ashore to the East End Seaport Museum for a Rum & Reggae After Party featuring live reggae music, rum-based cocktails, waterfront appetizers and an awards ceremony recognizing the top finishers in each racing division.
The after-party is open to the public, not just participating sailors and crews. Tickets are $75, with proceeds benefiting the museum.
Proceeds from the regatta will support the East End Seaport Museum & Marine Foundation and its work preserving and promoting the maritime history, culture and environment of the East End.
The museum occupies Greenport’s historic 1871 Long Island Rail Road station overlooking the harbor and serves as steward of several pieces of the village’s maritime heritage, including Bug Light and the Village Blacksmith.
By putting classic boats back on the water during one of Greenport’s biggest annual celebrations, organizers are hoping the regatta can connect that history with the village’s still-active maritime community — and establish a new annual tradition in the process.
The Bug Light Classic is being held with sponsorship support from M&T Bank and Mermaid Water Solutions.
