Before the Breakwater Yacht Club even existed, there was Wednesday night racing — and there is perhaps no other tradition that has as deep of an association with the community sailing center that is now in its 33rd year of existence.
There is no one better to tell the origin story of Wednesday night racing than Bruce Tait. The longtime sailor has owned and operated Tait Yachts, his yacht brokerage and yacht charter business in Sag Harbor, since 1982. He’s sold sailboats to countless Breakwater members, and has sailed his whole life, all over the world.
Weeknight racing is a tradition at yacht clubs and sailing centers around the country, and even the world, what many refer to as “beer can racing,” Mr. Tait said, but it didn’t exist in Sag Harbor until the mid-to-late 1980s, when Mr. Tait and a group of like-minded friends decided they wanted to start a Wednesday night sailing fleet.
“It was a resounding success,” Mr. Tait said in an interview earlier this month, adding that more than 30 boats showed up at the breakwater — the area that served as the start and finish line and would become the inspiration for the club’s name — for the first week of racing in the summer of 1987. That early success kept up.
“At the height of the fleet, we had even more boats than that, but it was very casual,” Mr. Tait recalled. “We kind of kept score, and we kind of didn’t keep score,” he said, with a laugh. “Nobody really cared. There was lots of hijinks going on, people throwing water balloons at each other. It was just fun on Wednesday night to go out and go sailing.”
While it was a decidedly more lighthearted affair than it would become in modern times, the Wednesday night races were the catalyst for the formation of the club. Breakwater Yacht Club was officially created the following year, in 1988, and racing was the reason.
“We were asked to host a regatta that had been held in East Hampton and by the Sag Harbor Yacht Club, called the Sag Harbor Cup,” Mr. Tait explained. “It would raise money for a local drug awareness program, which sounded like a good idea. In order to run a proper regatta, you have to be a yacht club so we said, okay, and we met in my office. We had probably about 50 people, and a bunch of meetings, and we did it.”
Mr. Tait served as the first commodore, and from that day forward, the club has hosted Wednesday night racing, rain or shine, every Wednesday night during a season that runs from May through October, only canceling races the week of the September 11 terrorist attacks.
The stories, inside jokes and other memorable moments that have accumulated over the years spent out on the water midweek are enough to fill a book, but Tait resurrected the tale of one particularly intense rivalry that had him in fits of laughter during the re-telling. During the first or second season of racing — Mr. Tait couldn’t remember exactly — he owned a J29 sailboat named Baby, which consistently would finish in second place behind a boat named Tidy Paws, a Soverel 33 sailboat owned by Jeff Briggs. On the eve of the last race of the season, when Mr. Briggs already had won enough races to have the season title in the bag, no matter the outcome, Mr. Tait said he and his crew decided “we have to do something about this.”
“So we hired a diver to go underwater to his boat and put fishing line around his keel and attached a big spackle bucket with a hole in it, so the water could flow through but it would severely slow him down,” Mr. Tait said, cackling in delight as he relived the mischievous joy the prank gave him decades ago. “At the start of the race, he’s normally out in front and as he’s tacking and sailing out away from the breakwater, he slowly drops back, and we get way out in front. He’s the last boat in the fleet and you can see him walking around the deck, furious, looking in the water trying to figure out why his boat is so slow. We were far away from him at this point but were watching with binoculars. Finally he rips his shirt off and jumps into the water and finds out what we did.
“To this day, he loves it,” Mr. Tait added with a laugh. “We still talk about it to this day.”
Because it was the last race of the season, Mr. Briggs had to wait a long time for revenge. Like Mr. Tait, he also availed himself of the services of a diver to even the score, having a diver tie a series of lines behind Mr. Tait’s boat to keep it attached to the pilings at the dock and prevent them from getting out for the race. But because he knew that Mr. Briggs would go for revenge, Mr. Tait said he and his crew had made a preemptive strike. Any satisfaction Mr. Briggs and his crew had derived from knowing they kept Mr. Tait’s boat tied to the pilings evaporated when they hoisted their main sail only to find that it had been adorned with bright red stick-on letters that read “BABY RULES.”
Those kinds of hijinks are a thing of the past, Mr. Tait said, with a bit of bittersweet nostalgia in his voice.
“You couldn’t do that these days,” he said. “The sailing got much more serious and became much more about winning. Sadly, that’s why the fleet has gotten smaller.”
Back in the heyday of those kinds of pranks, racing was “just an excuse to get out and go sailing,” Mr. Tait said. No one was flying a spinnaker, and races were just simple runs to the breakwater and back.
“Anything that’s competitive changes over time,” he said. “The quality of sailing improved, and the quality of sailors improved.”
Despite that evolution, Wednesday night racing has proven its staying power, and new traditions have sprung up as well. On a recent Wednesday night in May, the most competitive, high-stakes action, particularly at the starting line, was among the J70s, what Mr. Tait described as a “hyper competitive” fleet of smaller, one-design boats that don’t require the kind of handicap rating system used in the races of larger boats of different designs.
One thing that hasn’t changed over the years is accessibility. In a town and an area that has undergone massive changes since Mr. Tait and his friends started racing their sailboats in the 1980s — and has made many formerly affordable activities and pursuits prohibitively expensive for a lot of people — Breakwater Yacht Club has stayed true to its original mission of inclusivity.
“With waterfront prices being so exorbitant, Breakwater gives access to the waterfront for normal people,” Mr. Tait said. “It’s just like joining the Nature Conservancy; there’s no qualifications you need to have, you can just become a member. People are always looking for crew members.”
All that’s required, it seems, is a sense of adventure — and a sense of humor.