Photography by Andrew Chin
The sun had not yet set on the first day of racing, and Crazy Horse had already put 90 miles behind her. It was a downwind sled ride. She was blasting along at double-digit speeds with a red A3 spinnaker. Kites had been tearing around her, and boats were rounding up. The crew was hot on the heels of modern race sleds—a Reichel-Pugh 66, a Kernan 47, a Class40 and a Judel/Vrolijk 66—but they weren’t about to strike any canvas. They worked each wave to keep Crazy Horse on her feet and the bow pointing eastward at 16 knots of boat speed. Then they hit 17 while surfing down another wave. On board, the competition became heated: Who could hit the next top speed? And then, there it was—20 knots.
This was the 2025 Marblehead to Halifax Race, a 363-mile offshore run across the Gulf of Maine and along the coast of Nova Scotia. Crazy Horse, a 1990 Baltic 50, was crewed by the youth offshore team from the Community Boating Center of New Bedford, Massachusetts. For all but the coaches and one crewmember, this was the farthest offshore the group had ever been.
When the watch change came on the first evening, a pair of boots hit the cabin sole with a splash. Fifty to 60 gallons were sloshing about the cabin. “We are going to manage this,” the off-watch thought and quickly went to work. It had to be the result of more than just the slow leak from the lazarette hatches, they reasoned. Cushions were lifted and tossed, access hatches opened. As Crazy Horse surged down the next wave and the rudder came hard over to keep her on track, a stream of water ran forward from the steering compartment. On the next wave, eyes were on the rudder post’s stuffing box. Water rose up from it like a natural spring. A slow leak, fortunately. It was manageable. Any request to dial it back was either lost in the breeze or in the fun that was being had on deck. The water was pumped out and sponged, and the boat pressed on, slightly drier.
Night gave way to the rising sun and another challenge. “Something looked weird at the front of the boat,” one of the more experienced team members recalled. “We went to check it out, and our bobstay was loose. With bumpy seas and a kite up, this was a serious issue. The breeze had dropped and veered aft, and the boat was pausing more on each wave. The sprit was bouncing each time the spinnaker loaded and unloaded. It was only a matter of time before the sprit gave up.”
The quick-thinking crew secured a spare spinnaker sheet to the eye near the bow knuckle, a task that required dangling over the bow and getting drenched by the cool Canadian water. The line was then run through the front of the sprit and back to a winch via the jib cars. Crazy Horse, expecting at least 20 more hours of downwind sailing, was now fit out with an adjustable bobstay.
Morning was quickly eclipsed by thick fog; a game of pure boat speed had transformed into a match of wits, right as the CBC team rounded the southern tip of Nova Scotia. The A3 came down, and the big runner went up—the team was in downwind VMG mode. Dodging container ships and timing jibes, Crazy Horse worked her way north and east.
The youth CBC team crossed the finish line outside of Halifax after 39 hours, 21 minutes and 39 seconds. The mention of seconds may seem overly specific until you realize that they won the ORR2 class by only 34 seconds, beating out the venerable Sparkman & Stephens-designed Black Watch.
The mission was never to win. And while it’s hard to deny the competitiveness of the crew, the objective was to deliver valuable life lessons in teamwork, problem-solving and leadership. Some of the crew weren’t even aware of their victory until they were called to the stage at the awards ceremony. The only hint came from one crewmate who managed to hack the onboard Starlink router and access the race tracker.
I met up with this offshore team and coaches Richard Feeney, Andy Herlihy and Andy Chin last spring, to discuss the program and its bright future. New Bedford’s CBC offshore program has logged more than 7,500 nautical miles in four seasons with 150 participants. Crazy Horse was donated in 2025, but most training and racing has been on a pair of Figaro IIs—33-foot Beneteau one-designs dedicated to short-handed offshore racing but easily adapted to fully crewed youth adventures. The CBC program is an inclusive endeavor, welcoming youth participants of all ages, abilities and backgrounds through affordable and subsidized sailing programs. The center ensures cost is never a hindrance to participation.
Local events, such as the Whaler’s Race, have been an important part of the program. While they may not be as dramatic as entering a foreign country for the first time, the team revels in the experiences. Take their light air triumph in an Ida Lewis Distance Race, for example. After a tedious morning working ephemeral zephyrs up the west side of Block Island, they were becalmed north of the island. Other boats had spinnakers up, but none were full. A calm approach, aided by breakfast and hot drinks, helped lay a solid strategy of working in toward a light sea breeze along the coast. Protecting the shore side all the way to Castle Hill, they passed four boats and landed a solid mid-class finish. It was the best result for a CBC Figaro team in this challenging race.
Or consider the Vineyard Race that occured two weeks later, when the crew was a little late on the tide heading back into Long Island Sound. They shot Plum Gut, but no more than an hour later, the boats along the Connecticut shoreline began to lift in the forecast northerly. Thinking they may have been in the wrong place on the course, the crew set about studying and discussing the situation, and determined the inshore competitors had far less wind than they did. They worked the remaining sea breeze for lefties and were back in the lead by dusk, reaching for the finish line.
At the time of this writing, CBC’s Youth Offshore Team was setting its sights on the 2026 Newport-Bermuda Race, to kick off June 19. Their minds were spinning with unease about the Gulf Stream and the effects of the warmer temperatures near Bermuda on their endurance. How tired would they be after multiple days at sea? How much upwind work would the course throw at them? Would they be able to complete all the projects on board before the start?
This type of thinking is normal for any competitive sailor and a part of the adventure. Goals and the building excitement would keep the team driving forward. The finish line would be the universal focus, but visions of building patience and problem-solving skills also buoyed the crew. They were anticipating the offshore magic. It would be a night out, an evening with the stars, the sunset and fun people. “Whenever I feel that this is stressful or I’m tired, I just remember that the sun is going to rise, and it’s going to be beautiful, and we’re all going to celebrate and cheer and eat breakfast,” said one crewmember.
the sunset.
If anything, time with CBC provides these young sailors with a way to step away from life on shore, to disconnect from technology and connect with people. The shared experience is something the crew treasures. General curiosity and a desire to pass knowledge to others is part of this team’s culture. They recognize that everyone brings a different set of skills and knowledge and that it’s fun to see it all come together.
As I write, Crazy Horse’s freshwater system is receiving a complete overhaul, rudder bearings are being serviced, and the crew is tracking down fittings for older hardware. The team is becoming deeply familiar with every aspect of their ride to Bermuda. A safety-at-sea course is compulsory and so are practice sessions as New England waters thaw. And fundraising is a responsibility shared by all, but driven by CBC’s leadership.
“While our youth offshore team is racing to Bermuda, the finish line is only part of the story,” says coach Herlihy, who serves as executive director. “The real goal is to prove to young people everywhere that no dream is too big when you have the opportunity, support and determination to pursue it. By raising appropriate funds, we will train and equip our team, and share their journey in a way that inspires others to see that anything is possible. Together, we can transform a race into a story of courage, growth and leadership that resonates far beyond the sailing world.”
Each teammate has a different story of how they became involved with the organization. One person had taken a class in building skateboards that led to a class in boatbuilding. Another jumped right into sailing classes through scholastic partnerships before becoming a junior instructor. And another followed in the footsteps of older siblings. The offshore team has attracted youth from a wide range of backgrounds, and the multidisciplinary nature of offshore racing encourages this diversity. It also allows kids to be kids, like when a few teammates spoiled the spinnaker trimmer by hand-serving her bites of food between surfing waves on the way to Halifax.
The CBC’s offshore program is in the early stages, and it’s encouraging to imagine the impact this and similar programs could have on the sport of sailing. As we look across boatyards, sailing clubs and regattas, haven’t many of us wondered where the future of sailing resides?
Sailing has often been a sport handed down from one generation to the next, and not always well-advertised or made easily accessible. Many of us learned to sail because someone put a tiller in our hand and let us meander across the bay. If we want busy starting lines and cruising camaraderie decades from now, our youth need to breathe in sailing experiences today. The future of sailing isn’t hiding in foiling boats, a new rating rule, or the latest chart plotter. It’s in breaking down barriers to the sport. Organizations like CBC empower youth to explore oceans and lakes, and unlock their full potential.
There’s something uniquely durable about the education sailing provides. The wind does not care about anyone’s background. The tide doesn’t check a social media follower count. The ocean doesn’t forgive mistakes but often provides second chances for those who are prepared. A child who learns to read puffs marching across the water is unlocking pattern recognition. A teen who calls a layline is practicing consequence-based decision-making. These are not abstract concepts; they’re practical skills learned in one of the most dynamic environments on the planet. In a culture increasingly buffered from friction, sailing still offers honest feedback and builds teams through adversity.
As the name Community Boating Center suggests, it takes a village to make this happen. From mentorship to sanding bottoms to financial support, sailors need to show up for this to work. This isn’t nostalgia; it’s strategy. Getting more youth into sailing is about keeping harbors alive with curiosity and ambition. It’s about ensuring that the next generation sees the water not as a backdrop, but as a proving ground for skills that can be harnessed on and off the water. The CBC’s offshore team is changing sailing. There’s no going back, and this organization wouldn’t offer that option anyway.
This article was originally published in the August 2026 issue.
