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Coconut Grove Sailing Club (CGSC) kicked off its 16th annual Howler Regatta on Oct. 25, as more than 300 young sailors took to the waters of Biscayne Bay in one of South Florida’s largest youth sailing competitions. The weekend combined spirited racing with the club’s signature Halloween tradition: trick-or-treating at the Bay’s “Haunted Mooring Field.”
The two-day youth regatta welcomed competitors ages 6–18 racing in Optimist and ILCA (International Laser Class Association) fleets. Participants traveled from across Florida and neighboring states — including sailors from as far as Chicago.
What began in 2009 as a modest fundraiser with 50–60 participants has evolved into one of CGSC’s most anticipated annual events and a cornerstone of the regional youth sailing calendar. The Howler is one of two major youth competitions hosted by the club each year, alongside Miami Sailing Week.
“It’s not just about racing,” said Lauren Simpson, General Manager of CGSC. “It’s about creating a tradition kids look forward to — something that blends fun, family, and the sport we love. That’s how you build community.”
The regatta earned its name from both its Halloween theme and the notoriously blustery October weather that often disrupts racing. “No matter what, there’s always been a moment when the wind picks up and we have to pause racing,” Simpson noted. “It’s become part of the tradition. And this year, the Howler lived up to its name once again, with occasional rain and gusty winds — but never enough to dampen the fun.”
Regatta Centerpiece: The Haunted Mooring Field
The event’s highlight was the Haunted Mooring Field, introduced a few years after the inaugural regatta and now a beloved CGSC tradition. On Saturday night, club staff ferried costumed children in safety boats to approximately 25 decorated member vessels anchored in Biscayne Bay. The floating “neighborhood” transformed into a glowing playground of spooky lights and Halloween décor as young sailors trick-or-treated across the water.
“Think of it like a neighborhood with 25 houses — except those houses are boats,” explained Simpson. “The kids collected candy at each stop, and after about 15 minutes, they were back on shore grinning ear to ear.”
Six safety boats ran continuous rotations, cycling dozens of groups through the experience while parents and friends watched from shore, where the club offered games, snacks, and other festivities.
Safety Remains Paramount
Club staff — not volunteers — operated all transport boats, and every participant was required to wear a life jacket. Trick-or-treating was limited to regatta participants and their invited guests to ensure a safe, manageable environment after previous years saw overwhelming demand.
About Coconut Grove Sailing Club
A cornerstone of Miami’s sailing community since 1946, Coconut Grove Sailing Club is dedicated to advancing and celebrating the sport of sailing. As a nonprofit organization, CGSC provides exceptional, standards-based instruction at every level, preserves Coconut Grove’s rich maritime traditions, and upholds the highest national standards of safety, seamanship, and education.
