Wednesday Night Races

The New Suffolk Wednesday Night Races are a beloved summer tradition on Peconic Bay, drawing a vibrant mix of seasoned sailors and newcomers for a unique, informal racing experience. Unlike most regattas, these races are not officially organized, scored, or governed by any sailing association, including the Peconic Bay Sailing Association (PBSA). Instead, they operate on tradition, trust, and a shared passion for sailing, making them one of the most distinctive and accessible racing events on Long Island’s East End.

Each Wednesday evening from late spring through early fall, a diverse fleet of boats—from nimble dinghies to competitive keelboats—gathers off Cutchogue Harbor for the weekly race. The starting time is typically* 6:00 PM, with a warning signal at 5:55 PM, setting the stage for an exciting evening on the water. The racecourse takes sailors on a scenic route around Robins Island, with the direction alternating based on the date—clockwise on odd-numbered days and counterclockwise on even-numbered days—adding an extra layer of variety and tactical challenge. The starting line is located in Cutchogue Harbor, and the first buoy rounded is “BOB,” located off New Suffolk, a mark named in honor of Bob Fisher, a longtime supporter of local sailing. The race finishes an hour or so later in front of the New Suffolk waterfront.

While there are no official winners or race standings, the competition remains lively, with sailors fine-tuning their boat handling, reading wind shifts, and engaging in friendly rivalries. However, the true spirit of the event shines after the race, as sailors and spectators alike gather at the bar at Legends to recount the evening’s maneuvers over food and drinks. These post-race gatherings are an integral part of the tradition, fostering a close-knit community of sailors who come together to celebrate their shared love of the sport.

Though the PBSA does not organize, govern or score the races, anyone interested in joining—whether as a skipper or crew—can reach out to the organization or stop by Legends on Wednesday nights for guidance on the unofficial rules and customs of the event. This makes it easier for new participants to get involved, ensuring that the Wednesday Night Races remain an open and welcoming experience for all who wish to take part.

* Later in the season race start times shift earlier to accommodate diminishing daylight. When does this happen? As these races are unofficial, there's no set schedule.