Yacht racing ‘round Shelter Island in the annual Whitebread

The 27th running of the Whitebread ‘round the whirl sailboat race took place this past Saturday, Sept. 26.

The Peconic Bay Sailing Association sponsors the race, which is a spoof on the original Whitbread ‘round the world race. In years past, the Whitebread started in Cutchogue Harbor, circumnavigated Shelter Island and finished in Cutchogue Harbor, a course of about 34 miles. For the past several years, including last Saturday, the start line was Buoy N18, about half way between Jessups Neck and Nassau Point, much closer to Shelter Island.

There are six divisions and boats are grouped according to their PHRF ratings. A boat may finish dead last (as I have done many times) and correct up to a winning position(as I have done only once, sadly).

The race is held in late September or early October when the wind can be out of control and the weather foul. This year it was partly cloudy and in the 70’s, although the wind was generally light and gusty. The Whitebread is the season’s last large regatta held on the East End. This year there were 68 boats entered in the race, about half the number as years past. 

For only the third time since 1998, I was unable to sail in the Whitebread, but the following is the saga of the day’s events told to me by Linda Gibbs and Tom McMahon, who crewed for Jerry Zisfein on Hound, his 28-foot Johnston J28.

In addition to Tom, Linda and Skipper Jerry, the crew consisted of Dave Goldman and Steve Covey. Although one boat ran aground during the race, fortunately the services of Jerry, Dave and Steve, who are cardiologists, were not needed.

The wind was expected to be light, so the Race Committee ran course “Charlie,” a shortened course that runs the boats counterclockwise around Shelter Island. At the start it was only “blowing” around 5 knots. Because of some unforeseen difficulties, Hound broke a cardinal rule of sailing, one of the great sins, and was 15 minutes late for its 8:30 a.m. start (I won’t  mention the time I never made it to the start line because of a mutinous crew) but made up for lost time through good sailing and started passing some boats in its fleet by the time it reached South Ferry. 

Course Charlie bypasses Buoy Moa in Gardiners Bay, which meant boats could pass closer to Ram Island. At this point the faster boats had passed Hound and started flying colorful spinnakers, which Linda described as a “magnificent sight.” The wind was still blowing, well, blowing might be an exaggeration, but Hound was still moving.

After rounding buoy N6, Orient Harbor, Hound headed toward Fanning Point. They were still making pretty good time and beating some boats in their fleet until they neared the breakwater, where they sailed into a hole and the wind completely died. 

Unfortunately, I know just what that is like. Last year I was floating backwards in the same general area on Lotus.

Boats closer to Shelter Island had wind and were on the move. For 45 minutes, Hound’s crew twiddled their thumbs. I’m surmising that a gourmet lunch may have been served during that time. I only served ham and cheese sandwiches to my sometimes mutinous crews on Lotus. Linda has crewed for me for the last 10 years and I hope she will be back next year. I promise a better menu.

When the wind finally picked back up, Hound was in last place, with all boats in the fleet having passed her. Many sailors had given up and dropped out because of the light wind. Not so for Hound and her crew, true sailors. The diehards (Linda used a different term that I won’t mention) stayed the course. As they neared the shortened finish at Nassau Point instead of Cutchoque Harbor, they were approaching a boat in their fleet and really wanted to pass her so as not to cross the finish line dead last. 

It was bow-to-bow and they were pushing hard, but lost by a nose. I’m sure it’s just coincidence, but the exact same thing happened to me when Tom was my crew 11 years ago. As I always say, there’s always next year.

Hound placed 10th in her division, missing 9th place by only three minutes in corrected time, which is only seconds in real time.

Peter Beardsley, representing the Menantic Yacht Club, and coming off a first place finish in the Shelter Island Yacht Club’s Poor Memorial Race two weeks ago, placed 3rd in his division, missing second place by less than two minutes. This was his first Whitebread, and I’m sure not his last.

Congratulations to all sailors who participated — well done.