Taste of a trophy early in the Whitebread

ROGER McKEON PHOTO | The Whitebread race underway.

The Peconic Bay Sailing Association (PBSA) held its 18th Whitebread “round the whirl” sailboat race on Saturday, October 8. This race is a spoof on the Whitbred around the world solo race. The Whitebread is about 36 nautical miles in length, starting in Cutchogue Harbor, circumnavigating Shelter Island and finishing in Cutchogue Harbor. It is the last large regatta of the season held in the waters of eastern Long Island.

In preparing this article, I got a kick out of reading my Reporter articles from the past five years chronicling the highs and (mostly in my case) lows of the race. There was the time when I did not make it to the start line because the weather was so foul waves were breaking over my transom and flooding the cockpit, eliciting my cousin’s incredulous comment, “So you mean last beat you?” Then there were the multiple times when my crew mutinied because of the extreme conditions and I took DNFs (do not finish). I have also placed as high as fourth in several races. My current crew of the past four years has been lucky enough to experience only good weather, but we’ve still had our fair share of frustration.

ROGER McKEON PHOTO | Sailboats jockey for wind during the Whitebread.

This year, entrants numbered 124, just slightly less than last year’s record 131. There were six divisions with two classes in each division plus a multi-hull division. Boats are grouped according to their Performance Handicap Racing Fleet (PHRF) rating. A boat may finish dead last as I have done in the past and still outperform boats that finish earlier. There are a number of sailors from Shelter Island who enter the Whitebread. I do not know most of you, but I know that Segue captained by Bill Martens and crewed by his son Bill Jr. and son-in-law Josh entered as well as Licorice captained by John Somme.

The race is held on the first or second Saturday in October when the weather can be unpredictable. However, for the last four years, the weather has been sunny and warm if not hot. Unfortunately, in two of those years, the wind and tide combination has not been kind to the slower boats.

Flyer, my C&C 24, is one of the slower boats. The Race Committee staggered the starts of all the divisions. My division had an 8:35 a.m. start, which required leaving my mooring in West Neck Harbor by around 6 a.m. when it was still pitch-dark outside. It’s good for the soul to see the sky lighten and the sun rise and my crew of Dave Olsen and Richard Smith enjoyed the sunrise as much as I did. (Charlie Modica, a regular crew member, couldn’t make it this year.)

We powered to the start and had plenty of time to practice our starts. The pin end of the start line was favored. My crew and I could not believe it when just minutes to the final gun we were the only boat at the pin end. All the other boats were clustered at the committee boat. We hit the line at the gun in completely clean air, our best start ever.

In years past, I have forgotten to check the course at the committee boat, not that I know the difference between the A and B flags anyway. Not knowing the course usually did not matter because there were always boats in front of Flyer. This year the committee broadcast the race course over the VHF radio. It was a good thing that I was listening because for the first time in the 11 years that I have entered the Whitebread, Flyer not only lead around the first mark but she lead the entire fleet all the way to Paradise Point. It is at Jessups Neck, an earlier point, that one has to turn right for course A or bear left for course B.

We were battling Flying Buffalo, a Custom 36, to see who would actually round Paradise Point first. Flying Buffalo won by a boat length but not before they almost took out my back stay, rudder and outboard. We had been passing each other since Jessups Neck. Flyer had just passed Flying Buffalo when Flying Buffalo turned across Flyer’s stern and misjudged the distance. I turned around just in time to grab Flying Buffalo’s bowsprit and shove with all my strength to keep us from disaster. They apologized and no protest was lodged.

It is not often that we get to see the entire fleet behind Flyer but by the time we reached buoy MOA in Gardiner’s Bay, there were only about a dozen boats in front of us. It’s always a beautiful sight to see all those sails and spinnakers, especially (for a change) when they were behind us.

We were making pretty good time and were excited by the prospect of possibly taking home a trophy but the race was only a third over and we had a long way to go. When we rounded MOA and headed south, it was into a strong tide and we needed to tack three times before reaching Cedar Point and three more times before reaching South Ferry.

As we approached South Ferry, we stayed way to the left of the mark. The current coming off the point was so strong that all boats were sailing straight ahead but were being rapidly pushed toward the mark, a very strange sight. It was at this point that the fun and games began. The current coming down the channel was at least 2 knots and the wind was about 5 or 6. There were many boats in the small channel all trying to make it up and all having to tack and get out of each other’s way.

Every time a boat tacked, it was pushed backwards by the current. On top of the other competitors, there were the ferries. Many thanks to the ferry captains for being so careful and patient and for actually staying out of our way, even though they had the right of way.

It took a dozen or more tacks to finally escape the South Ferry channel and, by then, we realized we were running out of time because the race times out at 5:30 p.m. and it was already about 3:30 p.m.. By the time we reached Jessups Neck for the return to Cutchogue Harbor, many boats had withdrawn from the race knowing that they would not make it to the finish in time.

My crew and I realized we would not finish on time either but kept going out of a sense of disbelief that we had started out so well. And then …

Well, and then there is next year.