Brian McGinnes, representing the Wet Pants Sailing Association in Sayville, won the 44th annual World’s Longest Sunfish Race, Around Shelter Island, NY on Saturday in 4 hours 59 minutes 9 seconds.
It was McGinnes’ first circumnavigation of Shelter Island in a Sunfish, and he defeated a number of experienced sailors in this event, including last year’s winner, Mattituck Yacht Club’s John Condon. Condon placed second and missed becoming the only five-time winner of this nautical marathon by a mere 58 seconds.
Wet Pants Sailing Association, which has a very active Sunfish fleet, captured six of the top 10 places in the race.
The day was spectacular, with a beautiful, sunny sky, relatively low humidity, temperatures in the 80s and a forecast of six- to-eight-knot breezes from the west/southwest moving to the southwest by the end of the afternoon.
Founded and hosted by Southold Yacht Club, the race started about 200 yards off the yacht club beach after the race committee chairman, Charles Boyar, announced a clockwise course to the 38 Sunfish competitors. The breeze held as forecast and the leaders jibed into Gardiner’s Bay about an hour after the start. At Ram’s Head, the fleet was spread out but the clear leaders were McGinnes, Condon, Bart Hale of Southold, 89-year-old Dick Heinl (Seawanhaka Place Yacht Squadron), Jim Koehler (South Bay Watersports Association), Joel Furman (Wet Pants) and Joe Sullivan (Southold Yacht Club).
After passing Rams Head, things got interesting as the onshore breeze died and half the fleet caught up with the leaders. The first ones to break from the pack were McGinnes and Hale. About 20 minutes later, Condon and John Eckart of Massapoag Yacht Club in Sharon, Mass., who had won this event in 1982, ’84 and ’85, followed suit with the rest of the fleet catching the breeze about five minutes later.
By the time Condon and Eckart rounded Mashomack Point, McGinnes and Koehler had a half-mile lead on their way to the South Ferry. Because of the tide, which was still outgoing, those who stayed close to Shelter Island made out while those who sailed offshore — albeit with a better breeze — struggled and lost ground. By the time the fleet reached the South Ferry, the gap with the leaders had narrowed considerably and the lead started to change, seemingly minute by minute.
At the South Ferry, Koehler moved into first place followed by McGinnes, Condon, Lee Montes (Wet Pants) and 16-year-old Dan Sullivan (Southold Yacht Club), who was proudly flying the flag of Ireland from his upper spar. Shortly thereafter, Condon took the lead, followed by Koehler and Montes. The leaders stayed close to the Shelter Island shore and after passing West Neck Harbor, it was Condon, Montes and McGinnes leading the 38-boat fleet.
After entering Little Peconic Bay, the dogfight for first place continued. Passing Paradise Point and sailing into Southold Bay, McGinnes had recaptured the lead. Montes was still in second; Condon had dropped to third and Peter Wells (Wet Pants) had emerged from the pack to move into fourth place. Koehler had fallen back so it became a four-boat battle for the win.
Led by McGinnes, the three Wet Pants sailors tacked to the southwest to get as close to Great Hog Neck as possible while Condon continued sailing west, hugging the Shelter Island coastline. The three Great South Bay sailors became worried that Condon, the only North Fork sailor in contention, had local knowledge, which was going to doom their efforts. They started yelling back and forth, wondering if they should cover the four-time winner from Mattituck. Looking back over his shoulder, Condon may have thought, “I’ve got them.”
When the wind slightly shifted, Condon came about on starboard tack and sailed southwest toward the finish line. The Wet Pants sailors, however, had also come about and were on port tack, heading to intersect Condon. In the end, McGinnes was able to tack on Condon and maintain a loose cover to the finish line. Condon moved up from third to second place and led Wells (5:01:02) and Montes (5:01:11) across the finish line. Finishing out the top 10 were Koehler (5:06:52), Dan Sullivan (5:09:12), Hale (5:10:24), Joel Furman of Wet Pants (5:10:53), Conrad Volle of Wet Pants (5:11:16) and Brendan Cunningham of Wet Pants (5:15:11).
Afterward, Condon said: “This was the most strategic, competitive and fun race of all the races I’ve sailed around Shelter Island. Brian sailed a terrific race and I’m very happy to have placed second.”