Good Winds

  • The crew of the Too Elusive hauls up the mainsail.

  • Anchor chain on the Too Elusive.

  • Merle Hallett checks out the competition.

  • Sailboats of all sizes compete in the MS Regatta

  • Boats tack back and forth to prepare for the start.

  • Barbara Hallett, left, and Claire Watson, daughter of owner and captain Kitt Watson, at the navigation station on board the Too Elusive.

The annual MS Regatta celebrates sailing and raises money to help Mainers.

On the morning of August 20, 2016, a group of sailors about to compete in the 35th annual MS Regatta on Casco Bay gathered for a skippers’ meeting—a standard practice before any sailing race to go over the course and the rules. “We were given bags that had been decorated by someone suffering from MS,” recalls Lauryn Smith, skipper of the 25-foot Catalina Polaris. Inside the bag, Smith found a letter from a fellow Mainer, which she brought to her crew. It was a note from someone who suffers from MS, and it described how the money raised by the regatta would benefit people with her condition. Instead of beginning her day talking about strategy or weather, “we talked about this person with MS,” Smith says. “We talked about the people the race would benefit. We knew we were going to do pretty badly, but for us, it wasn’t about racing. It was about research. It was about people.”

Smith didn’t win that day. In fact, her boat was the slowest one in the race. But her all-female crew of beginners did receive another award: Most Spirited. “We called ourselves the ‘Flying Clams,’” she laughs. “We had a blast. It was an incredible day.”

Sailboats of all sizes compete in the annual regatta, which is part of the MS Harborfest, a three-day series of nautical events that takes place on the Portland waterfront. Festivities kick off on Friday evening with a silent auction and end with a lobster boat race and a tugboat race on Sunday afternoon. The cornerstone of the weekend is the Saturday MS Regatta in Portland Harbor.

The 12-mile course draws in big boats and small ones. There are seasoned sailors like Connecticut resident Arthur “Kitt” Watson, owner and captain of the 80-foot ketch Too Elusive, whose company, Watson Enterprises, is also the major sponsor of the event; and there are recent converts, like Smith, who lives in Portland. People come from Massachusetts, Florida, and beyond to raise their sails for the cause. “I’ve been in the MS Regatta for over 17 years now, and it’s a great charity that takes place in a very fun place to sail,” says Watson. “I have a big enough boat that I can take as many people as I want onto the race, which gives people who have never been on a sailboat an opportunity to experience a race from the water.” For Watson, the charitable aspect is the most important part of the MS Regatta, but sharing his passion for sailing comes in a close second. “I always bring beginners out with me. I love to teach them. And I love watching the smiles people get when the boat heels over—it thrills me to share that moment with them.”

Last year, I had the privilege of observing the race from the deck of Too Elusive. Also on board were Maine sailing legend Merle Hallett and his wife, Barbara. While Barbara handled navigation, Merle stood alongside Watson, his longtime friend, at the helm of the boat, watching as crisp white sails dipped in and out of sight in the thick afternoon fog. While on shore the August day had felt oppressively hot, the temperature on board was brisk, chilled by the vast waters of the Atlantic and the breeze that swirled through the bay, shifting directions swiftly and carrying droplets of water from the surf. The big boat cut neatly through the waves, and once the fog lifted, I could see the bulk of Fort Gorges from my perch on the deck. “This course was designed to be really fun for sailors,” Hallett says. “It’s not a straight shot.” Sometimes, he tells me, sailors like to go out and run the racecourse on their own, just for fun. “The turns are what make it enjoyable, and the islands are what make Casco Bay so beautiful,” he says.

Although he wasn’t captaining his own vessel, the race was still a win for Hallett, who, along with fellow sailor Dan Wellehan, came up with the idea for this charitable regatta back in 1982. The men and a group of friends had an open weekend in August, a passion for sailing, and an interest in giving back to their community. But when Wellehan—former owner of the shoe company Sebago, Inc.—suggested that the race benefit a disease called multiple sclerosis, Hallett looked at him blankly.

“A whole bunch of us said, ‘What the heck is that?’” he recalls. “And I said, ‘Look here, if nobody knows what it is, than that’s clearly the one we should do.’ And that’s just what we did.” The first year, the race started with 24 boats. Before Hallett retired in 2008 from his Falmouth-based business, Handy Boat, they were up to around 140 participating boats. Over the years, the MS Harborfest Weekend has raised over $3 million for the National Multiple Sclerosis Society. These funds help propel cutting-edge medical research and provide services to the more than 3,000 Mainers living with the condition.

“There’s a really strong sailing community in Maine, and they’re all very supportive of the regatta,” says Barbara Hallett. While there is an element of competition—“There are always competitive guys who really want to win,” adds her husband—most people are happy to see their fellow sailors do well. “Any time I have questions about sailing, I can always turn to someone locally—people in Maine want to help each other learn,” says Smith.

When it comes to racing, Smith has learned the importance of starting out strong. “Our only objective in the regatta was to have a really strong start, and to get across the line quickly,” she says. In order to achieve this “micro-goal,” as Smith puts it, she arrived early to practice. Before the race, she sailed back and forth parallel to the starting line, timing each run. Using lobster buoys as her markers, she figured out where she needed to be five minutes before the starter horn, where she needed to be three minutes before the horn, and so on. She paid careful attention to the weather, which can change quickly on Casco Bay. As her crewmates called out the time, Smith focused on managing the boat’s speed. “It was all about controlling the trim of the sails. At ten seconds, our sails were trimmed and we were going as fast as we could. We timed it perfectly so we were crossing the line right as the horn sounded.” She adds, “No one expected our boat full of girls to have a good start, and I think they underestimated us.”

Watson, like Smith, recognizes the value of setting simple intentions and following through on seemingly small goals. He has taught many children to sail (including his own) and one of his favorite things to do is step back from the helm and ask a student sailor to navigate into the harbor. “When you can bring a boat back to harbor on your own, there is such a confidence in that,” he says. “In today’s world, it’s important to get away from tablets and screens and focus on something bigger.” Sailing, he says, teaches values like personal pride, safety, and integrity. “But self-confidence, that’s the main thing,” he adds. “When you have confidence, you can thrive.”




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