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Great Chesapeake Schooner Race: One of the Bay’s Finest Traditions

A Ted Brewer Lazy Jacy 32 schooner during the parade of sail in front of the Baltimore Aquarium. Photo by Andy Schell
A Ted Brewer Lazy Jacy 32 schooner during the parade of sail in front of the Baltimore Aquarium. Photo by Andy Schell

The Great Chesapeake Bay Schooner Race is about seamanship and tradition; it’s about camaraderie and friendly competition; it’s about living in the moment. By the time you read this, the 23rd race will have been run and a winner crowned; but curiously, the Great Chesapeake Bay Schooner Race is not about racing at all.

Every fall, right after the Annapolis Sailboat Show, 40 schooners – from historic tall ships like Pride of Baltimore II to the replica Martha White with her crew of bluegrass musicians (really) – assemble for a week of celebration. And though that week includes a sometimes brutal 130-mile jaunt down the Bay, ask the schooner captains just why they come each year, and the answer likely will not be for the race.

Fells Point Rendezvous

The Great Chesapeake Bay Schooner Race begins in Baltimore where the vessels rendezvous at Broadway Pier in Fells Point. The Baltimore connection goes back to the very first race, when the late Lane Briggs aboard his ‘tugantine’ Norfolk Rebel challenged the Pride of Baltimore II to race the length of the Bay.

Capt. Briggs was an interesting man, and his Norfolk Rebel was an interesting boat – essentially a tugboat with a schooner rig. She earned her keep towing fragile tall ships and old boats full of character, including Jacques Cousteau’s famous Calypso. The notion that she could challenge any sailing boat to a race was certainly absurd, which helps explain why the race isn’t really about racing.

Today, the event’s official slogan reads “Racing to Save the Bay.” It is rooted in the cause of cleaning up the Chesapeake while providing educational opportunities for local youth, and it’s not a bad excuse for a bunch of sea dogs to get together and share their passion.

I last sailed the race in 2009 aboard Capt. Jennifer’s 74’ Woodwind. At Fells Point we rafted alongside the AJ Meerwald, an historic working schooner of 115’ that dwarfed us at the dock. I recognized many of the boats from the previous two races I crewed in. I spent much of the evening in the cockpit of Roger Worthington’s Prom Queen, sipping a rum drink and talking boats with his crew and the crew of Heron, Aram Nersesian’s 60’ aluminum schooner.

Traditional Seamanship

The Schooner Race is unique in that many of the traditional boats are just that. There is a decided lack of modern equipment on board, and the crew are sailors in the true sense of the word. Woodwind, though traditional in appearance, is one of the newer boats in the fleet, yet her instruments consist of a knot meter, depth sounder and hand-held GPS. We plan the route the old-fashioned way, with pencil, parallel rules and dividers.

The actual racing begins just outside Annapolis Harbor. In 2006, we’d enjoyed a brisk sail south from Baltimore, but just as the gun went off the wind died and 40 schooners suddenly saw their sails slatting. We tried hoisting our asymmetrical spinnaker but it was useless. Finally a breeze crept in from the south, building continually over the next few hours. Soon the fleet was hurrying close-hauled down the bay.

Capt. Jen was about ready to serve dinner when the extraordinary wind shift of 2006 caught the fleet by surprise. Out of nowhere an icy blast from the NW slammed the fleet, and suddenly we were broad-reaching in 30-knots.

Schooners, especially the gaff-riggers, are designed for downwind sailing, and suddenly the modern Marconi rig of the Woodwind was at a decided disadvantage to the larger Pride and Virginia, literally flying down the Bay with clouds of canvas spread from their top-masts right on down to the deck.

Sometime around 0200, Pride finally caught us. Rook Singer, my watch buddy, noticed running lights coming up astern of us, and a peek in the binoculars provided an incredible sight – the enormous silhouette of the replica 19th Century privateer with her wings stretched loomed on the inky horizon, a haunting image straight from the history books. She finally passed us to starboard, barely visible in the moonless darkness, not 200 yards away. Pride crossed the line first that year, and she deserved it.

Celebrating Sail in Portsmouth

The race finishes just off Thimble Shoals, but it’s a long slog – usually in the early hours of the dawn – into Portsmouth after you cross the line. What awaits is a weekend of revelry that only the schooner folk could provide. Most of the schooners are actually on their way south for the winter, either as private yachts or working tall ships providing tourist daysails. The Schooner Race provides a fantastic shake-down cruise and a welcome diversion.

Surrounding the wharf of the historic town, the schooners rest by the quayside after a long night of real sailing. Crews mingle from boat to boat, impromptu sea shanties bringing the history to life. It’s impossible to describe the feeling of camaraderie and fellowship that emanates from the wonderful schooner sailors, truly a group belonging to another age.

What I’ve come away with through each experience, is that the Race is truly not a race at all. Instead it’s a celebration of why we sail, a reminder that sailing is an art form, valuable simply for the sake of its enjoyment. Certainly the sailboat (and especially the schooner) as a mode of transportation is a relic of history, yet we continue to ply the seas at the pace of a slow jog, and seem to not only find this enjoyable, but even exciting.

Andy Schell is the former editor of All at Sea Southeast and a professional yacht captain. He and his wife Maria Karlsson recently completed their second west-to-east Atlantic crossing in as many years. Follow them online at andyandmia.net.

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