Come aboard a Chesapeake Bay log canoe for a race that’s fast, breezy―and wet.

By Steve Millburg
June 11, 2009
David Harp

Asked to describe his job aboard the log canoe Jay Dee, Geoff Moritz replies with a grin, “Ballast.”

He’s not joking. His duties this weekend will consist entirely of trying to keep a 35-foot sailboat upright. Geoff and a bunch of other crazy people get together several times each summer to race a curious―and beautiful―little fleet of Chesapeake Bay sailboats, even though the slightest breeze puts them in serious danger of capsizing.

Log canoes really are made of logs, usually three or five fastened together and then hollowed out and shaped to create a hull. A couple of centuries ago, the bay teemed with the sturdy, graceful craft. “They were your family pickup truck,” says log canoe historian Sidney Dickson. Watermen used them to harvest oysters and fish. Farmers filled them with crops to market. And when two or more boats were heading in the same direction, sometimes a trip turned into a race.

Fewer than two dozen log canoes remain, most of them built in the late 19th and early 20th centuries. All have retired from their working careers. About half still actively race. Their owners have turned these pickup trucks into sports cars by “overcanvasing”―piling ridiculous amounts of sail onto ever-taller masts―which makes them prone to capsizing. According to the rules of the Chesapeake Bay Log Sailing Canoe Association, the only penalty for sail area is an inability to keep the boat upright. “It’s self-handicapping,” says Pete Lesher, curator of collections for the Chesapeake Bay Maritime Museum in St. Michaels, Maryland.

Pete crews aboard Island Bird, built in 1882. Smallest of the canoes racing now, Bird must be tied securely to her dock. Otherwise, the weight of her masts will tip her over.

So how can anyone sail such a temperamental craft? That’s where Geoff Moritz and his compatriots come in. They scramble up and down 15-foot wooden springboards that stick out from the boat like pirates’ planks. The springboards and their riders counterbalance the pressure of the wind against the sails. Usually.

This particular weekend brings the first three-race set of the season, which runs from late June through mid-September along Maryland’s Eastern Shore. As an early-morning fog shrouds the water, crews ready Island Bird, Island Blossom, and Jay Dee―the minifleet operated by retired Judge John C. North II of St. Michaels. Friends greet each other with jokes and insults. New crew members hustle to make themselves useful. Everyone pitches in to lug the sitka spruce masts down to waiting boats. (Jay Dee’s 56-foot foremast weighs 400 pounds.)

Amid the camaraderie, three people prowl the dock, fretting about details and grimly recalculating to account for absent crew. Cory Penwell captains the 1892-vintage Island Blossom, the defending series champion. Dan North, John’s son, sits at the helm of the largest existing log canoe, Jay Dee, built in 1932. John skippers Island Bird.

“John is the most experienced log canoe skipper alive,” says Sidney Dickson, who will drive the chase boat for Bird, Blossom, and Jay Dee. “Even though he has the smallest boat, he’s won many, many many races.” He’s also a gracious host. Here at his home next to the Miles River Yacht Club on the outskirts of St. Michaels, John provides lunch both Saturday and Sunday for the crews of the three boats.

From shore, a log canoe race looks like a graceful ballet of pretty white sails. But the view from the deck of a spectator boat reveals sometimes-frantic choreography. Captains and crews ride the razor’s edge between maximum speed and disaster―in the words of one crewman, “teetering on the brink of control.”

A couple of the boats teeter over that brink and toss their crews into the bay―including Judge North’s shorthanded Island Bird. On the bright side, Island Blossom wins one of the three races and finishes second overall.

Back on shore, though Jay Dee didn’t compete as well as he’s hoped, Dan North’s intense game face has relaxed into a contented smile. Win or lose, he says, “It’s a lot of fun, and we’re fortunate to have wonderful people to sail with.”

Maybe these guys aren’t so crazy after all.

For a race schedule and much more, visit

Originally published in June 2006