By Tom McKeon


© Celia Withers

Twenty-nine years is arguably a milestone for any event. This is exactly what will take place October 1, 2022 when the Peconic Bay Sailing Association’s Whitebread 29 race committee’s horn sounds!

Like any great event, the Whitebread had humble beginnings. Twenty-nine 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.

Most years the Whitebread is a sailor’s delight. Last year saw 70 degrees, moderate winds, and was truly a spectacular October day. Some said they’d never sail in the race again because it was just too perfect a day! But as all sailors know, we’ve seen light air where racers were forced to anchor when the wind wouldn’t permit progress against the tide, we’ve had almost too much wind as the fleet was bashed going around the “MO-A” buoy in Gardiner’s Bay, we’ve had fog, and we’ve had buckets of rain. Every year is different, and every year is special.

Today, the Whitebread attracts 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 at a local venue, telling stories from the day’s adventure and adventures past, as 29 years ago. The starting line has moved east from years past, from New Suffolk to N18 in Little Peconic Bay, to accommodate sailors coming from further East. The race will finish in Cutchogue Harbor at C1.

The post-race party location will be announced in the near future, where the race results, prizes, trophies and plenty of talk of the day’s adventure will surely abound! To find more information, and to register, go to and click on Whitebread 29 October 1, 2022. ■