The Port Jefferson Harbor Cup was established in 1988 by the Setauket Yacht Club (now called Port Jefferson Yacht Club). There were four founding sponsor’s who helped kick it off:
- The Village of Port Jefferson Chamber of Commerce
- Danford’s Inn
- The Record Newspapers
- Chase Long Island
In it’s early years it was a huge event, not only for the sailing races, but also for the after race events which included the “Taste of Port Jefferson” in which many village restaurants provided a buffet of great food!
It was set up as an inter-club event, where a club would win the cup if they had at least 3 boats participating and had the best scores.
The Winners (as near as we can find in the records) have been:
1988 Setauket Yacht Club (SYC)
- Barrister III
- Free Flight
- I.O.M.A
1989 SYC
- Barrister III
- Free Flight
- I.O.M.A
1990 Mount Sinai Sailing Association (MSSA)
- Barrister III
- Garuda
- Prowler
1995 SYC
- Carpe Diem
- Ragtime
- Ranger's Charlie
1996 SYC
- Carpe Diem
- Ranger's Charlie
- Renegade
1997 MSSA
- Insatiable
- Odyssey
- ZigZag
1998 SYC
- Anemone
- Jetstream
- Ranger's Charlie
1999 SYC
- Carpe Diem
- Ranger's Charlie
- Renegade
2001 MSSA
- Lucky Star
- Stressless
- Anomaly
2002 SYC
- Intrigue
- Jiminy Cricket
- Panache
2004 SYC
- Gypsy Wind
- Panache
- Ranger's Charlie
2006 SYC
- Ragtime
- Ranger's Charlie
- Worthy Opponent
