When Chris Robinson met Tom Hall at a Christmas party in 1995, Hall was coaching the USM sailing team out of a Carolina Skiff that didn’t have an engine – so Robinson, a sailor since childhood and new member of the USM Foundation, raised money to buy him an engine.

Two or three freezing practices later at Centerboard Yacht Club in South Portland, the outboard fell off the transom of the little Carolina Skiff. Robinson helped raise money for a second engine.

“At that point,” he remembers, “I said I’ve got to get more involved.”

What’s now known as SailMaine all got started when Win Fowler, a professional sailor from California, moved to Maine in ’92. Fowler, who’d worked for an American’s Cup syndicate and had his own sailmaking business, incorporated SailMaine as a 501c3 around 1996.

That founding spirit of education “was written into the DNA of SailMaine,” says Fowler. He hoped to one day get a program going along the lines of Sail Newport that would recruit more high-level racing opportunities to Maine. But, he admits, “Not much happened until Chris Robinson stepped in.”

Three years later and the USM team, equipped with a new engine (this one would last) and with Robinson’s help, had relocated to the old Portland Company land at the end of Thames Street. Local kayaking nonprofit Rippleffect was getting its footing on the same stretch of waterfront and Phineas Sprague, whose family owned the property, had a fledgling “Sea Scouts” summer sailing program going in tiny wooden boats called Frosties.

Sprague remembers the day when he decided he would make the property adjoining Portland Yacht Services available for a community sailing program. He was sitting in his corner office when he saw three kids jump off the seawall and try to swim out to one of the moorings. He and a couple of coworkers went out in a dinghy to pull them out of the water, he said. Sailing “was a heritage in the family” for Sprague, who learned to sail in Turnabouts on Prout’s Neck and finished the last leg of an around-the-world trip in 1977.

“The vision was to give these kids something that they needed to be proud of and also give them something to do,” Sprague puts it, but “we had to make a bunch of mistakes before we got things rolling.” He remembers paying Tom Leach, once the Harbormaster of Woods Hole, Massachusetts, $35 apiece for paper cut-outs of the Frosty dimensions and hauling wooden closet poles back from the Hardware store to serve as masts. A group of at-risk high schoolers were paid through a federal program to build the little boats out of plywood and glue, painting them in the colors that (along with a splash of gel coat or two) still decorate the surviving Frosties today.

Fowler’s SailMaine now included four high schoolers, six USM students, and a small hoard of 8-11-year-olds who were coming through Portland Parks and Recreation, all sailing from a series of floats and ramps off the Portland Co. campus. Then Robinson raised the money to purchase twelve 420s from Yale University and Sprague and Fowler got insurance for the Frosty program through US Sailing. The USM team petered out and High School race teams started to form, first by a handful of students from Falmouth and Yarmouth under the name “Casco Bay Sailing.”

“They were used hard,” Robinson remembers of that first fleet of 420s, which all had strange names, the memorable among them being “Bizarre Gardening Accident.” At that point though, the Frosty sailors were joining 420 race teams as they aged out of their first boats and the program was really starting to gel. Sprague remembers appreciating how sailors who learned in the tippy, temperamental Frosties knew “the joy of having the boat tell you you did a good job – you didn’t need the coach to tell you.”

“The boat is part of them;” he put it wryly, “they’re wearing it like a pair of pants.”

Around 2009 Jeff Cumming, formerly a coach, became SailMaine’s first Executive Director. The community programs, which now include sailing days for school groups and regular visits by a host of local nonprofits, got off the ground in 2005 and were kickstarted in 2013. That was after the formation of the adult program brought in more capital and a fleet of twelve keelboats, the J22’s. True to Robinson’s resolution years earlier to make the Portland waterfront accessible to all, SailMaine moved to city land in 2011 adjoining the Portland Co. property, where it remains.

When Fowler incorporated SailMaine, he remembers hoping that “it would be an injection of life to the sailing community in Maine.” That certainly has proved true – and, Fowler adds, “it’s certainly grown far and away from my initial vision.”

Today, SailMaine serves over 150 high schoolers in a robust fall and spring race program and offers sailing exposure and instruction to hundreds of local kids each summer. As always, commitment to serving the community has taken center stage. As Robinson puts it: “our goal is to make good humans – if we can accomplish that, and they are also good sailors, then we’ve won.”

SailMaine is closing in on it’s 30th year in 2026!