Chasing the Wind: The Thrill of Log Canoe Racing on the Miles River
By Ferry Bridge Host
August 6, 2025
There’s nothing quite like a Chesapeake Bay log canoe under full sail—massive white wings catching the breeze, crewmen perched on long springboards, defying gravity with every tack and jibe. It’s thrilling, it’s historic, and it’s pure Talbot County.
These elegant wooden vessels—some over 100 years old—aren’t museum pieces. They’re part of a living tradition kept alive by a passionate fleet of sailors and spectators who gather each summer to witness a uniquely Eastern Shore spectacle: log canoe racing.
The roots of these boats run deep. Early watermen carved them from giant tulip poplars, using multiple logs to create workboats for harvesting oysters and crabs. But by the mid-1800s, the work turned to play. Informal races began on weekends, with sailors sprinting to shore for bragging rights—and sometimes better prices at the market.
By 1920, the sport had dwindled to near extinction. Then came a revival. A handful of Easton locals restored three historic canoes and founded the Miles River Yacht Club in 1921. The club didn’t just preserve history—they made it. In 1927, they introduced the Governor’s Cup, a now-iconic regatta named for then-Maryland Governor Albert C. Ritchie. The canoe Magic took the first title and remains a fierce competitor nearly a century later.
Held each summer, the Governor’s Cup race unfolds just downriver from Ferry Bridge, near the mouth of the Miles. On race day, it’s not unusual to see families with binoculars lining the shore or tailgating from moored boats. The sails rise high above the horizon, crews hike out dramatically, and boats heel so far over it seems they might capsize—yet somehow, they don’t.
Today, about two dozen canoes race across the Bay, each with a name as storied as its hull: Island Blossom, Flying Cloud, Mystery. Watching them is like stepping back in time—but with sunscreen and cell phones.
If you're lucky enough to be in Talbot County in late summer, catch a race and cheer them on. It’s not just sport—it’s heritage. And in Talbot, heritage still sails.
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