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(Credit: Victoria Caruso)

On Wednesday summer nights, crowds flock to the New Suffolk waterfront to watch a magnificent fleet of colorful sailboats race around Robins Island. Born from a shared love of sailing, these friendly weekly races have evolved into a cherished community tradition, serving as a source of local pride for sailors and spectators alike.

“We’re just out there to have a good time on our boats, but it’s fascinating that, from the standpoint of people sitting on the beach and looking out, it’s part of the way that they enjoy their North Fork experience,” said David Kilbride, commodore of the Peconic Bay Sailing Association. “We’ve been seeing more and more references to Wednesday night racing from the spectator standpoint as being kind of an environmental sort of aesthetic of the North Fork.”

The concept of Wednesday night races is not unique to New Suffolk; it’s a tradition that has found a home in coastal communities across the United States, from Ketchikan, Alaska, to Bristol, Rhode Island. Fondly referred to as “beer can races,” they bring sailors together once a week for a friendly competition, often followed by lively celebrations at local bars.

New Suffolk’s races began in 1978. While working at Windward Sailing Company, Fred Endemann, a seasoned sailor who spent his summers growing up navigating the waters of New Suffolk, joined a fleet that participated in weekly races in Greenport, inspiring him to introduce the tradition to the community of New Suffolk.

Playing a pivotal role as the testing ground for the first submarine commissioned by the U.S. Navy, the New Suffolk waterfront is renowned for its deep shorelines and protected waters.

“It’s the best sailing on the East Coast,” said Endemann, who continues to race each week in an Alerion Express 28 named Windsong. “My whole life is basically wrapped around Wednesdays. I make sure I don’t have anything else going on.”

Photos by David Benthal

According to Endemann, the charm of the Wednesday night races lies in their informal nature. Unlike traditional organized races, there are no fees, scoring or official notice of race.

While most skippers are affiliated with the Peconic Bay Sailing Association, the races operate independently from the organization. There is no single person in charge.

Instead, the races rely on a grapevine of word-of-mouth communication and a loose thread of emails to signal the start and end of the season.

“There’s no sign-up. One never knows from one week to the next who’s going to show up,” explained Kilbride. “Typically [a new member] would ask a friend of a friend to give them the lowdown here.”

“You absolutely do not need to be a member of the PBSA to participate in the Wednesday night races,” added PBSA race committee chair Peter Carroll. “Any Tom, Dick, or Harry with a boat can show up.”

Every Wednesday, weather permitting, sailboats line up at the starting area at 5:55 p.m., awaiting a five-minute warning from the horn of a powerboat manned by a volunteer. As the clock strikes six, the boats take off, navigating a course peppered with permanent government marks and other buoys.

To account for the different makes and speeds of boats, skippers of smaller, slower boats are afforded a slightly altered course, skipping a buoy or two to sail a shorter distance.

Central to the race is “Bob,” the first buoy the sailors pass on their way out of Cutchogue Harbor. Aptly named after Bob Fisher, an old sailor in the community, the buoy is strategically installed by the sailors each season off New Suffolk beach to keep the action close to the shore and give spectators an up-close view of the racing boats.

After rounding the first buoy, sailors will travel clockwise around Robins Island if it’s an odd day of the month, or counterclockwise if it’s an even day. This clever system keeps the races interesting, while still keeping the rules simple enough to follow. Factors like wind, weather, tide and currents also introduce an element of unpredictability that keeps the races engaging.

“Every week is different and that’s one of the things that’s so exciting about it,” said Kilbride. “There are nights when it’s pretty calm out there and then there are nights when it’s as exciting as you want it to be.”

Depending on weather conditions, the duration of the races can vary from an hour to two hours, although only a small portion of the race is visible to onlookers on the shore.

“I always tell people, if you want to see some sailing, go to New Suffolk at six o’clock to watch the start. Then, go to Legends or Minnow, have a nice leisurely dinner and then about an hour and fifteen minutes later it will be finishing and you’ll get to see all the exciting parts,” said Endemann.

Last year, Peter Carroll spearheaded an initiative to enhance the viewing experience from the shoreline by introducing stadium races. He designed a course that is about the same distance as the race around Robins Island but centers on “Bob” so that every bit of the course is visible from the waterfront.

“There’s been a big increase in the spectators from the shore, so we’re sort of hoping we can leverage that to get some more sailors out there,” explained Carroll. “We’re trying to attract new sailors and members, but also give them something to see even if they never become a sailor — just to make it more fun.”

This summer, he’s planned two stadium races, including one on Aug. 9 at 6 p.m. He also plans to educate spectators by supplying informational handouts about the course the boats will be sailing.

Photos by David Benthal

In part, the growing number of spectators along the shore can be attributed to the efforts of The New Suffolk Waterfront Fund. This 501(c)(3) nonprofit organization has been dedicated to developing the area into the scenic destination it is today.

In the early years of Wednesday night sailing, sailors would follow each race by spilling into The Galley Ho, a waterfront restaurant. The historic building, believed to have been constructed during New Suffolk’s thriving oyster industry in the late 1800s, eventually closed its doors in 1988, leaving the property abandoned for decades.

When plans emerged to develop the 2 1/2-acre site into a boat storage yard with a restaurant and parking facility, local residents established the New Suffolk Waterfront Fund to stop the development. Through community fundraising efforts and the support of the Peconic Land Trust, the organization acquired the dilapidated former restaurant and the surrounding property in 2009.

Since then, the iconic Galley Ho building has been revitalized, and the area has undergone a remarkable transformation. It now serves as a vibrant community hub with amenities such as a picnic area, community garden and a charming beach offering picturesque views of Cutchogue Harbor and Robins Island.

“If you go back 15 years, hardly anybody would show up to watch… you were really roughing it if you wanted to do that,” said Linda Auriemma, an NSWF volunteer and former board member. “More people come to watch the races now because there’s a nice place for them to watch them from.”

Auriemma herself is an avid spectator at the Wednesday night races. She says it’s an opportunity to get out and stay connected with community members. “It’s a fun place. The kids can have a little freedom and run around on the grass,” she said. “When they have 30 boats going, it’s really quite a sight.”

This summer, a new sustainable seafood restaurant called Minnow at The Galley Ho opened inside the historic building that housed the original restaurant. While many enjoy viewing the races while eating on the restaurant’s deck, owner Andrea Tesse is also offering a picnic menu for those who prefer to enjoy their dinners a bit closer to the action along the shore.

When the races conclude, sailors gather at Legends and Minnow to unwind, enjoy a meal and engage in lighthearted banter, playfully teasing their fellow competitors.

“You come up with really good rivalries,” said Endemann. “Bill Coster and myself are best friends. We’re also best rivals. We battle each other every Wednesday out there.”

“I enjoy the camaraderie a little more than the competition,” said Coster, a Laurel resident who has been racing for almost 35 years. ”Being older, it’s nice to have younger people who want to talk to you.”

“It’s a wonderful group of people,” he added. “We all look out for each other.”

Wednesday night sailing also serves as an opportunity to introduce newcomers to the sailing community.

“Most of us will invite somebody new on from week to week, a house guest or somebody who’s interested in learning more about sailing out here,” explained Kilbride.

“I meet complete strangers and I tell them ‘Hey, I’ve got an extra seat on my boat,’” added Endemann.

In the past, the sailors have partnered with Old Cove Yacht Club, an association that offers junior sailing lessons in New Suffolk, to give its students experience on larger sailboats.

While the official PBSA season finishes with the annual Whitebread race in early October, Wednesday night sailing carries on until it’s too cold to continue, sometimes lingering as late as mid-November.

“There’ll be a couple of emails saying ‘Okay, I’m pulling my boat,’” which then signals the end of the season, explained Kilbride.

As winter settles in, sailors and enthusiasts eagerly await the arrival of spring, when the Wednesday night races will once again paint the waterfront with vibrant sails and the timeless spirit of this beloved community tradition.