A sunny and exciting Whitebread Race

The 25th running of the “Whitebread ‘round the whirl” sailboat race took place Saturday, September 30. The Peconic Bay Sailing Association sponsors the race, a spoof on the original Whitbread ‘round the world race.

The Whitebread is the season’s last large regatta held on the East End of Long Island.

For 23 years the Whitebread started in Cutchogue Harbor, circumnavigated Shelter Island and finished in Cutchogue Harbor, about 34 miles. This year and last year the start line was moved to 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 sunny and warm, although the wind was light.

This year, only 70 boats entered the race, about half the number in years past.
During Friday night’s skippers’ meeting I was mesmerized by a poster on the wall that showed all the T-shirt designs from the previous Whitebread races.

I started counting and realized I had participated in the Whitebread 16 times, the first in 1998, and though I only have one trophy to show, I have lots of exciting memories. Would Saturday end my dry streak?

With the start line closer to Shelter Island, my crew and I boarded Flyer, my C&C 24, in daylight instead of total darkness as in years past. I really missed watching the sunrise while motoring to the start line, but the extra hour of shuteye was welcome.

Usually I have three crew, but with light wind predicted I only needed two, Dave Olsen and Linda Gibbs, both of whom have been my crew for the last nine or 10 years.

In previous years, the Race Committee staggered the starts of the different divisions by 10 minutes, but on Saturday, there were rolling starts. The gun sounding the start of one fleet was also the warning for the start of the next. One did not want to be over early and have to sail back across the line, especially with another fleet in the way.

Coupled with very light but gusty wind and a downwind start, we held back slightly to ensure no over early call. With a long race ahead of us, I figured a few seconds wouldn’t matter.

Flyer was the fourth slowest boat in the entire fleet according to its PHRF rating of 248 which put us into division 6 with the first start at 8:30. There were 12 boats in our division. When the start gun sounded we had a straight line to the first mark, N14, in Shelter Island Sound on course Bravo, clockwise around Shelter Island. We knew we would be fighting the tide all day but did not realize just how bad it would get until nearing Hay Beach.

We were doing fairly well and keeping up with a number of boats in our fleet, and the wind was strong enough to get us around Fanning Point and towards North Ferry. We made just one bad tacking error in that time. We, or I should say I, did not see a boat below me and tacked onto a port tack right in the path of a starboard tack boat. I had to throw the tiller over to get out of the way, costing us some time, but nothing compared to what happened in Hay Beach.

We were sailing along, passing some boats in our fleet and hoping to catch a few others. We passed North Ferry and the breakwater off Greenport and were heading toward buoy 7 off Hay Beach. Just as we reached Hay Beach the wind completely died, and we started drifting backwards, and worse, toward a dock in Hay Beach. To avoid hitting the dock I was reluctantly getting ready to start my motor, which would have resulted in instant disqualification, when a barely noticeable breeze moved us away from the dock just enough to keep going.

A few boats in our division were far enough in front of us to miss the windless hole we and a number of others found ourselves in, causing a number of boats to drop out. That half hour of drifting was painful.

Finally, we started moving again in the right direction. It was about noon, and unless the wind really picked up we knew there was no way we were going to finish the race by the 5:30 p.m. cutoff. Fortunately, the Race Committee announced it was shortening the course to buoy G15, at South Ferry, which allowed us to finish the race with time to spare. Flyer finished 21 out of 44 boats in the non-spinnaker division, and sixth of 12 in division 6. Now I’m already looking forward to next year.

Shelter Island was well represented in this year’s Whitebread, including Jerry Zisfein on Hound, Stephen Guyer on Alliance, Harry DiOrio on Bella, James Eklund on Jul Bocken, Jonathan Russo on Sachem, Scott Woodrick on Heritage, Peter Dinkel on Varuna, and Scott Matthews on Fantasy.