What began as a friendly wager between two captains has grown into a beloved Chesapeake Bay tradition that raises hundreds of thousands of dollars for local nonprofits while celebrating the region's maritime heritage.
WATCH: Beer bet becomes beloved Chesapeake Bay sailing tradition
The Great Chesapeake Bay Schooner Race will launch Thursday from Baltimore, featuring 23 boats racing 118 nautical miles from where the Key Bridge once stood to Norfolk, Virginia.
"We're just going to race down the bay, drag race. It's going to be very epic," said Kayden Lewis, who is crewing his first race aboard the Sultana.
The race traces its origins to a simple challenge between two ship captains 36 years ago.
"Father challenged the captain, Captain John Miles, to a race down the bay with the Norfolk Rebel and the Pride of Baltimore too. Winner had to buy a beer, and it was, you know, just a fun challenge," said Stephen Briggs, whose father started the tradition.
That friendly competition has since raised over $350,000 for nonprofit organizations throughout the Chesapeake Bay region, including the Downtown Sailing Center, Chesapeake Bay Foundation and oyster recovery projects.
"Throughout the year it's not just a one time a year event. There's a lot of stuff going on throughout the year," Briggs said.
Beyond fundraising, the race serves as a platform for sharing the love, history and tradition of Chesapeake Bay watercraft. Briggs said his father, who lived and worked on the water, was passionate about sail training and working with children.
"It started out as a fundraiser and then it morphed into more of an educational, an awareness of the Chesapeake and everything else," Briggs said.
For Lewis, that educational mission resonates deeply. The Sultana holds special significance as the first schooner he ever sailed on as a fifth-grader.
"They taught us everything about the boat itself and the history of the Chesapeake and what the boat originally did," Lewis said.
The race showcases traditional schooners like the Pride of Baltimore 2, connecting participants and spectators to the maritime heritage that has shaped the Chesapeake Bay region for centuries.
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