By Tom McKeon

October 7, 2023 was the 30th Anniversary of the Peconic Bay Sailing Association’s Whitebread Race. The race had all the hype and anticipation of a Super Bowl, and it certainly didn’t disappoint. Taking place on Long Island’s Peconic Bays, the race’s name is a play on the significantly more arduous Whitbread Round the World Race.

The wrath of Hurricane Ian played havoc with Whitebread 29 last October. Fog, Southeast winds from 18-30 knots, current against wind creating treacherous waters, and oh yes, a steady horizontal pelting rain,made it one for only the hardiest of the hardy sailors (I wasn’t among them).

As October 7 approached, I was watching the weather like a hawk. The week prior, we quickly went from shorts and tee shirts to jeans and fleece, and the long-range forecast was showing rain and wind for October 7. I quickly emailed the captain of my ride to lobby for setting sail no matter what the weather; I wasn’t going to sit this one out! The return email informed me of engine problems on the boat, and we were withdrawing from the race. Yikes, not again! Seeing as captains have their permanent Whitebread crews for years, and other crew start lobbying for coveted open spots months in advance, I thought I’d be watching this one from the committee boat. As word got around, I was graciously offered a spot by Capt. Bill Archer on Optimistic, an Alerion 28. I jumped on it faster than a discounted boat slip. Sailing comradery at its best!

The weather forecast had been ominous. The wind had been blowing heavily out of the east for a week. That morning at the dock there were discussions of reefing, and I wondered if I’d brought enough dry clothes.

This year we were lucky. The 30th Anniversary Whitebread would begin in Cutchogue Harbor to honor the legacy of the starting place of the original Whitebread, and it just happened to be right outside the creek where we were docked. We powered out expecting the worst, but that was far from how the day unfolded.

As expected, the winds were fairly stiff at 15 knots out of the east. As we rounded “R20” at Nassau Point and headed towards Jessups Neck, the sailing Gods smiled upon us. No rain, 10-12 knots, and warm weather. We were applauding our superior sailing acumen by not reefing! In fact, in the lee of Shelter Island we could have used a small gale.

It was nearly a perfect day. Our spirits were high, I couldn’t believe I scored a crew spot at the last minute, and the captain and crew of Optimistic were all thankful to be a part of such a historic Whitebread. It was just a great day to be on the Peconic Bay. I had never sailed an Alerion in this type of race and was excited to see the fierce, dare I say cutthroat, competition in the class. The Alerions were within a few boatlenghts of each other for quite a while.

As we were rounding Mashomack Point on the southeast side of Shelter Island, the captain decided to cut the corner in order to make up time on the Alerion ahead of us. Everyone went wide to avoid running aground, but we went in. As I sounded off the depth gauge going down foot by foot, then yelled out ‘three feet!!” I heard the captain exclaim, “No guts, no glory!” I was just happy I didn’t have to get out and push!

As with all Whitebreads, the comradery and stories of the day’s race abounded at that evening’s party and awards ceremony at Safe Harbor Stirling in Greenport. This year saw the return of the pre-covid party, with a live band, cocktails, dinner and awards ceremony. It was truly a successful Whitebread 30 as no one was injured, no boats were lost, and all proceeds from the race will go to support youth sailing.


Andrew Baris’ Sabre 402 Impulse finished third in PHRF Non-Spinnaker.   © Celia Withers


The PBSA Whitebread Committee would like to thank everyone who participated in the race, and the many, many volunteers who make it happen, from setting up the technical aspects of the race, race committee, party organization, raffle sales, gear sales and support. We’d like to give a big Thank You to our sponsors Safe Harbor Stirling, Preston’s Chandlery, and OneSails, and acknowledge the overall winners. First overall in the Spinnaker division was Peter Beardsley and the crew of Glory Days, representing Menantic Yacht Club/Shelter Island Yacht Club, and the Non-Spinnaker winner was Philip Walters and the crew of August Sky from Lloyd Harbor Yacht Club/Centerport Yacht Club.

Whitebread 31 is tentatively scheduled for September 28, 2024, and we look forward to seeing everyone out on the water for another great event supporting youth sailing! To find more information on the PBSA and the Whitebread, go to ■