Sebago Supports the Sailing Spirit of Maine

On a late summer afternoon Portland Maine’s working waterfront hums with activity. Lobster boats unload their traps, ferries from Casco Bay Lines zip back and forth to Peaks Island, Chebeague and places beyond. Nestled down on that waterfront, right at the southeastern foot of Munjoy Hill, a gaggle of white sails swarms around a dock and begins to lean into the breeze. This dock belongs to SailMaine, and the fleet of fittingly named Optimists, eight-foot, single-handed, junior sailboats, takes to the bay as kids laugh and adjust their rigging. Beyond them further offshore, high school teams sharpen their racing skills on Turbo 420s, while back on shore, a few newly recruited adults are ready to learn the basics, perched on the keel edge of discovery and the first sparks of a passion for sailing. It’s something many of these current and soon-to-be sailors only admired from shore their whole lives, that is, before SailMaine. After all, sailing is for everyone—or at least it should be.

Founded in 1996 on Portland Harbor, SailMaine was built on just such a notion, something that was then a radical idea: that sailing should be accessible to everyone. Not just for wealthy summer people, or yacht club commodores, SailMaine would make sailing open to all as a vehicle for personal growth, a mode of connecting to nature, a source of community, and even a potential career path. Outfitted with donated boats and a borrowed dock, SailMaine’s founders began offering sailing programs for kids, adults, and families who might never otherwise set foot on a sailboat. What started as a small breeze has since blown into a full gale and one of New England’s most dynamic community sailing and education centers. Today, more than 1,500 sailors a year learn, race, and play on Casco Bay through SailMaine programs. From junior summer camps to high school racing, adult learn-to-sail courses and adaptive sailing programs, SailMaine instills in the community that the heritage sailing, tradition of seamanship and the spirit of the outdoors—and especially the sea—are for everyone.

At Sebago, we share that same spirit, and that’s why we’ve sponsored SailMaine and their mission to connect people to sailing at any and every stage of life and ability. Sebago has been sailing in Maine since our founding over 75 years ago. It’s our passion, it’s our heritage, and there’s still nowhere we’d rather be out on the water than the coast of Maine. Founded in 1946, Sebago built its reputation on handsewn craftsmanship and timeless style, launching the iconic Docksides® boat shoe that became a global symbol of life by the water. For generations, Sebago has outfitted sailors, explorers, and weekend adventurers with footwear designed for both topside and dockside. What truly unites Sebago and SailMaine is their shared Maine heritage, tradition, and passion. Both are rooted in this coastline of granite and pine, where the sea shapes not only the geography, but also the culture. It’s not uncommon, in fact, to see Sebago Docksides dotting the SailMaine docks—on the feet of coaches, parents, or sailors just stepping off the water. It’s an historic, authentic connection that’s sewn into daily life in Portland’s harbor.

As SailMaine approaches its 30th anniversary in 2026, its mission feels more vital than ever. In an age where screens dominate much of daily life, the organization is putting hundreds of young sailors out on the water each summer, teaching resilience, confidence, and teamwork. In 2004 SailMaine’s 150 sailboats provided 4,400 hours of free sailing for all. They had over 550 summer camp participants and served 226 high school sailors on eight competitive teams. Not only that, SailMaine’s offerings and outreach have grown over the years. This year they helped 657 underserved youths with free programs and gifted almost $50k in need-based scholarships.

And through their Horizons Sailing program, run in partnership with the Adaptive Outdoor Education Center they hosted over 100 adaptive participants in a program aimed to remove barriers to sailing experienced by individuals living with disabilities.

So when you make your way to the SailMaine dock in Portland Harbor, stop and look around. Take in the history of the working waterfront and wonder at the throughline in Maine heritage that connects that waterfront to those kids learning, racing and out on the water in front of you. You just might spot a pair of Sebagos—the same shoes that have been part of this story for nearly 80 years. Two Maine originals. One mission: to bring people closer to the water, to adventure, and to keep the sailing spirit of Maine alive.