“Virginia boats can’t sail” was the challenge from Johnson Hines, owner of Flying Cloud, Maryland’s title-holding log canoe. Garland Miller, a highly competitive sailor and Mathews County native, took exception to that remark and in the summer of 1937, rigged up a 32-year-old Poquoson-style log canoe for battle in the Miles River off St. Michaels, Maryland. “Log canoe” can bring to mind a rustic, prehistoric contraption, but these local developments of indigenous dugouts have evolved into highly refined sailing vessels. Maryland log canoes have moved even further from their working roots to promote speed over other important traits, such as stability. They fly clouds of sail from multiple masts and are kept upright by a ship’s company of off-season linebackers, who clamber up and down portable “hiking boards” to keep the right-side up. According to E.V. Brewington’s “Chesapeake Bay Log Canoes,” Virginia log canoes came to be called “Poquoson” canoes, since the ultimate Virginia model e...