By Tom McKeon

How many sailing events can proudly proclaim a 30-year anniversary? That’s exactly what will happen when the Whitebread 30 race committee’s horn sounds on Saturday morning, October 7. The Peconic Bay Sailing Association is kicking off 30 in a big way and pulling out all the stops, starting with a Skippers meeting Friday night. After the race there’s dinner, beer/wine, awards – and even the return of the band! – all at Safe Harbor Greenport in beautiful Greenport, NY.

Let’s rewind to the start. Like any great event, the Whitebread had humble beginnings. Thirty years ago, after a weekly Wednesday night summer race around Robins Island, a small group of New Suffolk sailors gathered at the Galley Ho restaurant and decided (after a few cocktails, from what I understand) they wanted to end the season with an adventure. The “Whitebread,” a play on the significantly more arduous Whitbread Round the World Race, was born. They decided to sail a race around Shelter Island, starting and ending in New Suffolk.


After Hurricane Ian crashed the party last year, Whitebread 30 organizers and sailors are primed for classic fall conditions.  © Celia Withers


Many years the Whitebread is a sailor’s delight…except last year of course! Hurricane Ian came barreling across the country, descending on Peconic Bay with fog, SE winds from 18-30 knots, current against wind creating treacherous waters, and oh yes, a steady, horizontal pelting rain that made Whitebread 29 one for only the hardiest of the hardy sailors. In full disclosure I wasn’t one of them, as I was happy to sleep in and listen to the wind pelt rain against my windows at 6:30am. Seventy-three boats registered for the race. Eighteen started. Twelve finished.

The year prior, Whitebread 28, was truly a spectacular October day. Some said they’d never sail in the race again because it was just too perfect a day! Every year is different, and every year is special. Now that we’ve gotten a hurricane-fueled Whitebread out of the way, we’re owed another great day of sailing on the bay, so register now!

I spoke recently with one of the original Whitebread organizers about his thoughts on three decades of “racing ‘round the whirl.” “Seems like yesterday,” he said. “After thirty years we must be doing something right.” He reflected on the comradery of the original group, and the sailors that came from all over the bay to participate in the original Whitebread. He said after the race, the party was always crazy. At night, the mooring field outside New Suffolk Shipyard was full of boats that stayed from the night before. “If those barn walls could talk…” he mused, pointing to the barn at the New Suffolk Shipyard.

Today, the Whitebread attracts more than 70 boats annually from all over Long Island, the Peconic bays, and Connecticut, and is the largest fixed keel boat race on Eastern Long Island. It has the same post-race, libation-fueled comradery, telling stories from the day’s adventure and adventures past, as they did thirty years ago.

The Whitebread 30 starting line will be in the vicinity of “C1” in Cutchogue Harbor (to honor the tradition of the original Whitebread sailors), with a finish at “N18” in Little Peconic Bay. Be sure to attend the post-race party at Safe Harbor Greenport, where the race results will be announced, prizes awarded, with dinner, plenty of beer and wine, a live band and plenty of talk of the day’s adventure! For more information and to register, go to and click on Whitebread 30 October 7, 2023 on the home page. ■