By Sarah Stebbins
Photos by Aliza Eliazarov
From our January 2025 issue
On a raw, overcast afternoon last winter, members of Mostly Maine Frosty Fleet No. 9 arrived in the parking lot of the Kittery Point Yacht Club, in New Castle, New Hampshire, and began unloading miniature sailboats from their pickups and sedan trunks. One by one, they lugged the diminutive watercraft to the edge of the Piscataqua River, which straddles Maine and the Live Free or Die State, lowered themselves into the tiny cockpits, and tacked their way toward a tiny racecourse.
Approximately six feet long and weighing about 35 pounds apiece, the dinghies, known as Cape Cod Frostys, are the world’s smallest racing sailboats. And Mostly Maine is the world’s only fleet still competing in them. Eleven sailors bundled in dry suits and beanies showed up on this day to tackle a roughly half-mile looped course. Most steered tidy, hand-built wooden boats with glossy, candy-colored hulls. But the afternoon’s champion after the results of six races were tallied was Eli Slater, who piloted a battered white craft patched with duct tape and splotches of brown epoxy. “There’s a part of me that likes it because you look at that boat, and I’ve got this stained life jacket, and you’re like ‘pfffft,’” he said over beers in the yacht club afterward. “And then you’re like, ‘wait, that guy just beat me?’ The boat can look ratty, but it can be fast.”
Cape Cod Frosty sailboats are not sold commercially. Many racers build their own; others, including commodore Kali Sink (pictured here and in the blue boat, above), purchase used dinghies.
Former Cape Cod harbormaster Tom Leach conceived the Frosty in 1984, wanting to extend the sailing season. The idea was to design a boat that was compact and lightweight enough to tote around in a car and launch from the shore after docks had been pulled out of the water for the winter. Over the next two decades, 15 fleets sprang up across the United States and Canada. Peter Follansbee and a couple other sailors from the Kittery Point Yacht Club (which was originally based in Kittery) formed the Mostly Maine fleet in the late ’80s. The members, most of whom hailed from the Pine Tree State, built their own boats with plans ordered from Leach and raced together on Sundays from November to May. A few competed in a national championship held annually on Cape Cod. But by the time Follansbee hung up his dry suit, in 2010, Mostly Maine was the only Frosty fleet still afloat. “Fleets come and go,” he says. “You need people who are willing to go out of their way to keep them going.”
Today, commodore Kali Sink is among the Frosty faithful. One of three Mainers on the fleet, she organizes the season’s racing schedule (including a national championship that attracts a handful of far-flung sailors to New Castle) and arrives early to set the course before weekly competitions. Sink competed in her first Frosty race three years ago, drawn to the community vibe and the thrill of tacking in a teensy boat with her body inches from the frigid water. “It’s all just kind of ridiculous,” she said as she steered the Boston Whaler chase boat — used to rescue capsized sailors, who are a fairly common site in choppy conditions — toward a float where the fleet gathers before races.
A mix of expert and newbie Frosty sailors proceeded to wing around the little course, sometimes hopping into each other’s boats to test them out and sharing them with folks who didn’t have their own. (Mostly Maine records sailor names on its scoreboard, rather than sail numbers, allowing racers to trade dinghies without a penalty.) During the final race, the wind died and the last sailor, who was new to the sport, struggled to reach the finish line. She called to the group to go ahead and start packing up, but they stood around on the float, offering strategies to help her power through the remaining couple yards. “I’ve been on fleets where if you show up with zero experience and try to race, they would treat you horribly,” Slater said later. “This fleet is really good about not being that way. Because who wants to spend a Sunday freezing with a bunch of assholes?”
