The 10th annual Village Cup Regatta will set sail on Saturday, Sept. 8.

The event, presented by the Port Jefferson Yacht Club, is a friendly sailing competition between Mather Hospital and the Village of Port Jefferson.

The two teams, which race in the Port Jefferson Harbor, are both raising funds for non-profit organizations.

The village fundraises for Lustgarten Foundation’s pancreatic cancer research, while Mather Hospital supports the Palliative Medicine Program.

Private funding has ensured that 100 percent of every dollar finds its way into the program.

Since its inception a decade ago, the Village Cup Regatta has raised $509,000. Even with the race being canceled last year due to choppy waters, the organizations still raised around $70,000.

Here’s how the day goes:

Festivities will commence at Harborfront Park at 10 a.m. when Regatta t-shirts will be sold and signed by actor Ralph Macchio — the event’s director. (This is Macchio’s seventh year working the regatta).

Commemorative t-shirts will also be sold, along with hats and nautical bags.

At 11 a.m., the crowd will head to the Port Jefferson Village dock for the Memorial Parade of Boats. Then, the boats will race in one of three classes at Harbor Front Park — according to boat size.

All Regatta sailboat participants will cruise through the park, dressed in banners and nautical flags. The option to view the race from a spectator boat is being offered at $50 per person.

A Skipper’s Reception will follow the Regatta at 3:30 p.m. in the restored (1917) shipyard building, better known as the Port Jefferson Village Center.

Here, the winner of the Village Cup will be honored.

Tickets to the reception are also being sold at $50 each to raise funds for the cause.

Those who would like to attend both the reception and board the spectator boat can do so at $75 a ticket. Individuals, businesses, and organizations can fund the two programs by sending donations on the Port Jefferson Yacht Club website. Sponsorships are also available.

For more information and to purchase tickets visit:

For more information about this event contact Charles Chiaramonte at

Top: Sailboats participating in the yearly Village Cup Regatta. (Credit: Facebook)