The Whitebread at 25: Race around Shelter Island an East End tradition

Sitting on bar stools at the former Galley Ho restaurant in New Suffolk on a fall evening in 1994, a small group of skippers planned a way to cap off the sailing season. 

Instead of just another of their usual weeknight excursions around Robins Island, the sailors would navigate their boats on an even longer trip around Shelter Island, starting and ending in Cutchogue Harbor.

The race would be called The Whitebread, a play on the Whitbread, a venerable round-the-world race now known as the Volvo Ocean Race.

“The decision was made over a couple of beers,” recalled Mike Drobet of Mattituck, a founding participant and early champion of the race. “We thought it would be a great way to end the year.”

They had little reason to believe the event would ever become the institution it now is.

The boats sail out of Cutchogue Harbor. (Credit: Grant Parpan)

This past Saturday, 72 boats sailed in Whitebread 25, a regatta many have come to count as their favorite event of the year.

“It’s more challenging than most any races in the area,” said Tom Wacker of Cutchogue, who has sailed around Shelter Island in the Whitebread annually since 1997. “We went to a Newport race week earlier in the summer and most of the races you’ll find, you don’t get the kind of currents you get going around Shelter Island.”

It’s that unique geology, with only narrow channels separating the island from Greenport and North Haven, that creates a heightened experience during the race. Mr. Wacker describes it as the “cork in the bottle of the Peconics,” creating fast currents and wind that fellow sailor Dave Kilbride of Nassau Point says “whips off land masses in different directions.”

“Then you blow past Shelter Island and suddenly you’re in Gardiners Bay and much bigger waves, much rougher, stronger winds,” Mr. Kilbride added. “So there’s a lot of contrast as we do this Whitebread Race from the shelter of Cutchogue Harbor, on the one extreme, and Gardiners Bay on the other.”

Aida Kuehn, who sailed along with her husband, Chris, and 5-year-old son Dan in the very first Whitebread, said they learned the hard way just how tricky the race could be. Of course, she had the added distinction of being five months pregnant with their son Stefan for that inaugural event.

She recalls that the weather was really bad that first year and the three-person crew felt the effects of it once they hit Gardiners Bay.

“My 5-year-old was trying to steer,” she recalled. “My husband was doing the sails and I needed to go to the bathroom every five minutes. So it was a really trying and exciting and crazy day.”

On Saturday, Ms. Kuehn was one of about a half-dozen spectators gathered at Cedar Beach in Southold to witness the starting leg of the race. They carried cameras with them to document friends and loved ones as they participate in what’s become an East End staple. Similar small gatherings occur each year on Shelter Island and other spots on the North and South forks. The sight of dozens of sailboats breezing by is something to behold, the spectators will tell you.

At its height, the Whitebread, which is organized each year by volunteers from the Peconic Bay Sailing Association, attracted about 125 boats from across the region. While that number has been cut in half in recent years — a trend consistent with sailing all over — there are still more boats entering the race than originally envisioned. Mr. Drobet said word of mouth and advertising efforts grew the number of participants from nine in 1994 to about 30 boats the following year. It took off from there.

Race chairman Bill Coster of Laurel said he first sailed on a friend’s boat for Whitebread 3 and has skippered his own vessel each year since.

“I didn’t finish the race,” he said of his performance in Whitebread 4. “I actually got hit in the head with the boom and I retired, as they say.”

The view from onboard “Trading Places.” (Credit: Michael Versandi)

But Mr. Coster continued, becoming one of the events more successful sailors, with three first-place finishes, an achievement he attributes to upgrading to a better boat, surrounding himself with a strong crew and gaining more knowledge himself. Among the crew members on his boat this year was Willie Fisher, another of the Whitebread’s founding members.

“I usually sail with extremely good people,” Mr. Coster said. “They’re smarter than I am and the boat’s faster than I am, so it’s a good combination. I make very good sandwiches.”

Asked if the Whitebread is more about competition or camaraderie, race participants say it’s a combination of both. They enjoy the social aspect of the event, which includes a post-race party at which they all share the stories of the day, but most of them are also out for victory.

“I don’t know anyone who doesn’t really want to win,” Mr. Wacker said. “But I think it’s a real good group of people out there. Good sports. I think most of us try like hell to win.”

Asked if that’s true for him, too, Mr. Coster answered with one word: “Yes.”

Mr. Kilbride, a longtime weekender on the North Fork and relative newbie to the competition, connects more to the social side of things.

“The group of people with whom we sail is varied. It is all sorts of backgrounds; weekenders, locals, men, women,” he said. “It defies stereotyping. And we are all great friends. That’s the one thing you can say that we have in common.”

Attracting newcomers will be the challenge of the Whitebread moving forward. The decline in participation is related to a growing interest in power boats, Mr. Kilbride estimated, adding that on his casual sailing excursions in the Peconics, he’s observed a shift in the types of boats he sees out on the water.

One way new sailors are getting involved in the Whitebread is through East End Youth Sailing, which had a crew of area high-schoolers compete this year. At the helm was skipper Dan Kuehn, the former 5-year-old who steered through rough conditions in the very first Whitebread.

As his mother walked Cedar Beach in Southold Saturday to get a closer look at the boats, she had a chance encounter with another mom whose son is on this year’s team.

“It’s very exciting,” said Jordi Krupnick, whose son Matthew, a Mattituck High School student, was sailing in his first Whitebread. “He was up this morning raring to go at 6 a.m., all ready to jump out on the boat.”

The crew of “Trading Places.” (Credit: Michael Versandi)

Even for established Whitebread veterans, the race day excitement is still there.

“I don’t sleep that well [the night before],” Mr. Coster said. “I spend a lot of time on preparation. I’m nervous until after the start and we’re on our way and you kind of feel settled on the boat. The start is the most trying, intense part of the race.”

It isn’t until the race is over, when you see the other boats coming in around you, that you truly get to enjoy the experience, the sailors agreed.

“That’s when you go into the beer cooler, which has been sealed shut to that point,” Mr. Kilbride added.

While stormy weather has made for quicker speeds and challenging times on the course in past years — even sinking a boat in 2014 — the 25th installment of the Whitebread was plagued by dull winds. That dominated the conversation at the post-race party, where the honorary chair, Captain Pat Mundus of Greenport, was recognized along with the original sailors from 1994.

The start of the race from Cedar Beach. (Credit: Grant Parpan)

Ultimately, the finish line was moved up Saturday to account for the poor conditions. Skipper Lee Oldak, sailing his boat Purple Haze out of the Breakwater Yacht Club in Sag Harbor, finished with the top adjusted time of 4 hours, 21 minutes, 47 seconds. August Sky, skippered out of the Lloyd Harbor and Centerport yacht clubs by Philip Walters, finished first among all non-spinnaker boats.

While a lack of wind might have dampened this year’s race, there’s little doubt the Whitebread will continue for years to come. To hear the participants tell it, there’s simply nothing like it.

“I have done some longer distance races, but I find this one satisfying, if not the most satisfying,” Mr. Coster said. “You’re racing in your home waters. … The conditions here are as good as anywhere up and down the East Coast.

“This is a gem that people are really unaware of.”

[email protected]

With reporting from Michael Versandi and Krysten Massa