Whitebread Regatta caps off season: Glory Days takes overall first place

The Whitebread Regatta unfolded Saturday in nearly ideal weather after tropical storm Felipe, which had been barreling up the coast toward Long Island all week, suddenly —almost miraculously — dissipated the day before the race. 

Race committee member and veteran sailor Beth Fleisher had no idea. 

“I literally refuse to look at the weather report because you never know what’s going to happen until the morning of the race,” she said. “After many decades of sailing, I’ve just figured out that you wake up in the morning … and see what’s going on.” 

Race committee member and volunteer Lynda Corrado took a different tack: “I did a prayer to the weather gods … I always do. I’m a character.”

Ms. Corrado, who described the regatta as the “Superbowl of sailing,” was in one of several race committee support boats spread out across the course.

“There’s a passion involved in sailing,” she said. “When you have the sun beating down on you and the wind in your face, your hair is getting blown all over and you’re fighting the elements. It’s a test of ‘Wow, can I overcome the elements?’ It’s also a test of prowess: Can I overcome the current, the water and the wind, and make my boat go as fast as possible?” 

The regatta, sponsored by the Peconic Bay Sailing Association, raises money through a raffle and entry fees to provide junior sailing scholarships to local teens through three foundations: Old Cove Youth Sailing, East End Youth Sailing Foundation and Breakwater Youth Sailing. 

This year, the racers set out from Cutchogue Harbor, sailed around Nassau Point, down past Jessup’s Neck and then around the South Ferry on Shelter Island. From there, the boats head past Sag Harbor and Mashomack Preserve toward Orient Harbor. Then it’s back toward Greenport and across Southold Bay into Shelter Island Sound. From there, it’s a right turn to the finish line, located about halfway between Paradise Point and Nassau Point in Little Peconic Bay. 

The race was split into eight division — three for spinnakers and five for non-spinnakers. Glory Days, captained by Peter Beardsley, took the overall first place in the spinnaker category, while Phillip Walters rode August Sky to an overall first place in the non-spinnakers. 

The winners in each of the eight divisions were Spinnaker Division 1: Jim Sanders, Team Tonic; Spinnaker Division 2: Peter Beardsley, Glory Days; Spinnaker Division 3: Don Suter, Hokus Pokus; Non-Spinnaker Division 4: Philip Walters Jr: August Sky; Non-Spinnaker Division 5A: Bill Coster, Silent Passage; Non-Spinnaker Division 5B: Fred Endemann, Windsong; Non-Spinnaker Division 6A: Michael Drobet, Wild Surmise, and Non-Spinnaker Division 6B: Mahlon Russell, Sea Breeze

Nearly 60 boats participated this year in the final race of the season — and every one of them completed the 30+ mile loop around Shelter Island, according to race committee member David Kilbride.

The regatta welcomed boats as small as 22 feet with no upper limit, though race committee chair Don Suter said most larger boats top out below 50 feet — after which “it’s too easy to run aground.” Crews ranged from a husband-and-wife team of two to 10 people. 

Unlike the summer Sunfish race around Shelter Island, the Whitebread Regatta is a handicapped race, meaning each boat’s size and weight is considered against more than a dozen different factors, including wind speed and sail size. 

“It’s complicated,” Ms. Fleisher said, “but that’s how we try and make it even — so that I, as a boat that’s 26 and a half feet long, can race against a boat that’s 40 feet long.” 

Ms. Fleisher’s J/80 keel boat— called Faster, Pussycat! Kill! Kill! — was crewed by a quartet of 20-somethings, she said. 

“This boat probably has the biggest asymmetrical spinnaker in terms of relation to the size of the boat out there — and we frickin’ fly,” she continued. “We spent a good portion of the race planing, which is when your boat sort of half jumps out of the water, like a physics thing … It’s one the best feelings possible.” 

Ms. Fleisher’s boat had more going for it than aerodynamics and a good crew, including a killer playlist that featured “everything from the Talking Heads to Bachman Turner Overdrive and David Bowie.” 

But it wasn’t all smooth sailing. 

“Just as we were leaving the dock, I looked down and I saw this plastic port that had a crack in it,” Ms. Fleisher said, and crew member Caroline Kyle raced to her car.

“The only thing we had to tape it up was duct tape with the band One Direction on it,” she continued. “[Caroline] got it at some event at college, like, years ago. So we had to tape up this very visible portion of our cockpit so that water wouldn’t get in and sink our boat with the faces of Harry Styles and One Direction. 

“They were our cheering section for the day. Every time I would turn around to look around the racecourse and trying to figure out what to do, Harry Styles was looking me right in the eyes. So that was pretty funny. We spent a lot of time playing Harry Styles and One Direction songs in homage to this.”

The name “Whitebread Regatta” is a nod to the Whitbread Round the World Race, started in 1973 and originally sponsored by a British brewing company of the same name. It is now simply called the Ocean Race. 

The Whitebread — which grew out of the decades-old tradition of racing around Robins Island on Wednesday evenings during the sailing season — was dreamed up in 1994 at the bar of what is now the Minnow at the Galley Ho in New Suffolk.. 

“There was a group of local sailors, about eight guys, and some of the guys were from those Wednesday night races. And they were at the Galley Ho saying, ‘We should have an end-of-season big blowout race with a party afterwards.’ And I think the first Whitebread Regatta had only about eight or 10 boats in the race,” Mr. Suter said, noting that the Whitebread has attracted as many as 130 boats over the years. 

Corporate sponsors of the event included Catered Fork in Southold, Greenport Harbor Brewing Co., Safe Harbor, Suhru Wines in Cutchogue and Preston’s Chandlery in Greenport, which donates a kayak for the after party raffle each year. The 10-piece Orient-based Linden Farm All Stars played the after party, which went until 11 p.m.

“To be able to celebrate our sport, to celebrate our season, to celebrate our friendships and the beauty of the North Fork and our bays is really something that is an absolute gift,” Ms. Fleisher said. 

 Mr. Suter said that passing down the sailing traditions to a new generations was vital to the sport. 

“Frankly, in sailing right now, a lot of people are getting older — like myself — and starting to age out of sailing,” he said. “Unfortunately, the next generation doesn’t always have the time and maybe not the patience or money to do it. Nowadays it seems like power boats are taking over. For people that don’t have enough time, they bought power boats and they zoom away for an hour or two and they’re back home again.”