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An Adventure with Chesapeake Bay Log Canoe Sailors

"You can travel around the world, sail on any and every boat, and you’ll never find anything quite like the log canoe.” With a pipe in his teeth and a beard on his chin, Mike Spicer may have been the first to drop this line, but he was certainly not the last.

"You can travel around the world, sail on any and every boat, and you’ll never find anything quite like the log canoe.” With a pipe in his teeth and a beard on his chin, Mike Spicer may have been the first to drop this line, but he was certainly not the last. This statement was the unofficial creed of the Chesapeake Bay log canoe sailors; ask any one of them about the boats they sail and eventually they’ll sing the same song. But it’s not until you board the 100-year-old wooden hull, step the 58-foot mast, hoist the 1,500 square feet of sail and scramble to windward on narrow wooden boards that you realize these sailors weren’t bragging: this is unlike any other boat you’ve ever sailed on.

The Chesapeake Bay log canoe is an enigmatic boat. These ancient craft are both a playground and a sanctuary to those lucky enough to discover them. During the Oxford Heritage Regatta in Oxford, Maryland this past August, I was one of the lucky ones aboard Jay Dee, a 1931 log canoe helmed by Dan North (Jay Dee was built by his great-great-uncle John B. Harrison) and crewed by sailors who were adamantly—if not parochially—devoted to the sport. We raced in light air, heavy air and chaotic air (cheers, Hurricane Bill) in a regatta that was as exciting as it was mesmerizing.

How to describe a boat that is often referred to as “indescribable?” Imagine a canoe that is 35 feet 6 inches long on her deck and 65 feet from bowsprit to boomkin. Jay Dee’s narrow sitka-spruce hull is just 8 feet wide and her carbon-fiber-skinned daggerboard reaches down 9 feet from her otherwise flat underside. Her two colossal loblolly pine masts require a dozen burly men to step them and, once rigged, they support three working sails (jib, foresail and mainsail), a kite (a gaff-rigged topsail), a staysail and an asymmetrical spinnaker, for a total of 1,500 square feet of billowing white canvas.

This skewed ratio of sail area to righting moment (there isn’t any!) creates the need for windward ballast even in a light breeze, hence the boards. Sixteen feet long and just a foot wide, these four hollow boards are jammed under the leeward rail and extend proudly over the windward gunwale, where the crew bear-crawl to the ends, sit on their thumbs, lock their ankles beneath them and attempt to keep the canoe upright. No one and nothing is tied down. It’s intense. It’s challenging. It’s mystifying. And it’s addictive.

It takes a specific breed of sailor to fall in love with the terror and the glee of the log canoe. (As it turns out, dangling from splinter-laden boards isn’t for everyone.) At the Oxford regatta there were only seven boats racing, but there were still plenty of hot tempers and amplified comments (or was it straight-up bellowing?) throughout the event. The starting lines were boisterous, the mark roundings were crowded, and once we crossed the finish line, it often felt as though the entire crew let out a cathartic sigh.

There are about 15 log canoes still sailing, but only about ten that race. Many are helmed and crewed by sailors who were born into the sport. Rarely does a log-canoe sailor just show up and start racing; you typically have to know someone to get aboard. These sailors are not elitist, nor are they evangelists. They’re members of a fraternity, and they’re bent on keeping it that way.

The crew of Jay Dee is no different. Many of them have been with the boat for a decade or more, and they run it like a family affair, each supporting the boat in his or her own way. Jib tender Bob Flower dedicates four to six weekends a year to working on Jay Dee and assists in her half-dozen annual tows between venues. Bowman Mike Spicer, a ship’s carpenter by trade, donates his talents to perfecting her woodwork; the gorgeous toerails, foresail traveler, longhead and sternpost are all his doing. Artist Marc Castelli photographs Jay Dee to use in his paintings and John Jallade writes about them at blogcanoe.com. “I tell Dan every year: it is a privilege to sail on Jay Dee and an honor to share in the camaraderie of such a fine crew,” said main trimmer Kathleen Redfern. “I’m a broken record…but I’m sincere.” For these sailors, log canoes are not just a hobby, they’re a way of life.

Jay Dee’s crew are by no means the first to fall in love with their boat. Their devotion echoes that of Chesapeake Bay seafarers who have been enjoying these canoes for centuries. In pre-colonial days the native Powhatans paddled dugout canoes—ancestors of the log canoe—until the British added sails for speed. Nineteenth century oyster-tongers took advantage of their shoal draft to navigate the Chesapeake and race back to shore with the day’s catch. As the oyster markets became more competitive, so too did the sailing, and fishermen tweaked their sails to get back first to fetch the highest prices for their catch.

In the late 1800s a man name William Sydney Covington built five racing log canoes: Island Bird, Island Blossom, Island Bride, Island Belle and Island Beauty. He passed his passion down through the generations all the way to his great-great-grandson Dan North (skipper of Jay Dee) and his great-grandson, the Honorable John C. North II, known locally (and formally) as “Judge.”

Today, the Judge is the granddaddy of log-canoe sailors: he is the class rulebook and encyclopedia. He can still remember the rogue years of log canoe racing when crew would drag their bodies beside a boat to slow her at the start. This was his 60th year racing, and he attended every regatta in clean-pressed white racing garb to helm Island Bird. At his home, “Canoe Harbor,” the crews of all three North family racing boats (Jay Dee, Island Bird and Island Blossom) meet to enjoy the Judge’s hospitality. In the summer, they strategize. In the winter, they comfort one another over a couple of greenies, pining for the days when the water will be warm enough to get back out sailing.

Back out on the boards of Jay Dee, I glance down at her hull and grin as I am enveloped in her history. I feel a part of something larger. I feel a kinship with the fishermen and rogue racers who came before me, a member of a fraternity of sailors too established and mysterious to comprehend.

“Tacking!” North’s shout from the helm jerks me back from my daydream. He eases the tiller over and instinctively the eight of us on boards slide into the hull and pivot, now facing aft. Wordlessly, we yank the boards from the leeward rail and heave them out over the new windward side.

Jam. Jam. Jam. Thunk (someone got punched in the bum). Jam. “Made!”

The sails are filling, the boat is beginning to heel; no time to waste. We scramble out on our boards and resume our positions. I lock my ankles beneath me and can see from the corner of my eye that my comrades have staggered their bodies along the boards to achieve optimal heel. I lean back and peer up the course, searching for oncoming gusts. I begin to feel that sense of engagement they all talk about—the almost meditative feeling of being completely aware of every tiny movement of your body, the boat and the crew.

Just as I begin to feel contemplative again, a puff hits and I realize we could capsize, and probably will at some point. We could hit a lull, plunging boards and crew overboard. I could lose my footing and smash into the person in front of me, destroying the crew’s choreography.

And then the grin returns. It is this juxtaposition of fascination and terror, of old and new, that coaxed me here in the first place. Somewhere between the mystery and the intensity, I have landed in an incredible microcosm of the sailing world. Then, with my legs dangling and my adrenaline pumping, I realize that the proverbial saying is spot on—this is unlike any sailing I’ve ever done. 

See the rest of the photos from this story here.

Photos by Bob Grieser, Dave Ostwind and Marc Castelli

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