What Makes a Race? The 2026 Great Chesapeake Bay Schooner Race
In 1988 Captain Lane Briggs, of the Norfolk schooner tugboat Rebel, challenged Jan Miles, of the schooner Pride of Baltimore II, to a race from Baltimore to Norfolk. The challenge was officially accepted in 1990 and the annual Great Chesapeake Bay Schooner Race was born. Time added more vessels, more “classes” and much more interest. Today this race is celebrated throughout the Chesapeake Bay each October.
This year’s race started on Thursday, October 15 at 12 noon near Annapolis. This Hampton Roads writer and crew watched from the race satellite tracker as the Annapolis charter boat Woodwind II shot out of the gate and maintained her strong lead throughout the race. Towards the end, we headed out to meet the winners in our ad-hoc committee boat near the Thimble Shoals Lighthouse. Woodwind II’s busy crew greeted us with broad smiles as she crossed the finish line in full sail.
Later at dock, new captain Delaney Vorwick, pointed to navigator Aiden Gray and said, “It was him!” Delaney told us her family-style crew was chosen because of their “eagerness and dedication.” She also saluted the legacy of former Captain Jennifer Kaye who, with her father Ken, built the charter business and became “schooner race royalty” until her retirement this year after they sold the business.
Although Woodwind II clearly looked to be the winner and was docked hours ahead of the trailing vessels, she wasn’t alone in the Freemason Harbor. Awaiting the final celebration “social” and open boat tours scheduled after the race were two more extra-ordinary vessels and crew: The Norfolk Rebel (Capt. Steve Briggs) herself and a rogue “mini tall ship” called Boojum (Capt. Joshua Haufle) that had pulled in on its way home from Portugal to join in the festivities. Captain Haufle laughed that he had singlehanded much of the way, with a little help from a “German” and a “one-legged Aussie!”
Following Woodwind II in “Fleet A,” were Adventurer, (Capt. Duncan Hood) in second and Tom Bombadil, (Capt. John Flanigan) in third. In AA Class, first place went to Norfolk’s Virginia (Capt. Michael Florentino) and second place to The Pride of Baltimore (Capt. Jan Miles). The winners in Fleet B and C were: first - Bonney Rover (Capt. Robert Suhay), second - Sea Hawk (Capt. Steve Nelson) and third - North Wind (Capt. Scott Hughes). Class N winners were Grace (Capt’s Dobbs and Susanne Fryberger) and Bennu (Capt. Marco Ovando). This year’s prestigious “Black Dog Trophy” went to Duncan Hood (Capt. of Adventurer).
- by Erik Speer
