The Great Chesapeake Bay Schooner Race (GCBSR) is an annual schooner race established in 1990 that takes place on the Chesapeake Bay. The race—held in October of each year—begins just south of the Chesapeake Bay Bridge near Annapolis, Maryland, and ends at Thimble Shoal Light north of the Hampton Roads channel, covering . Pre- and post-race activities take place in Baltimore, Maryland, and Portsmouth, Virginia, respectively. Proceeds from the race support Chesapeake Bay education and preservation projects. The current time to beat is 11 hours, 1 minutes, 41 seconds and was set in 2017 by the schooner Virginia. The previous time to beat was 11 hours, 18 minutes, 53 seconds and was set in 2007 by the schooner Virginia.

History The race started as a challenge from Lane Briggs, the captain of the steel-hulled, sail-powered tugboat Norfolk Rebel, to Jan Miles, the captain of Pride of Baltimore II. The first official race was held in 1990.

Results

Year Class AA Class A Class B Class C 2007 1. Virginia2. Pride of Baltimore II3. Lady Maryland 1. Woodwind2. Antonina3. Munequita 1. Adventurer 652. Martha White3. Sally B 1. Quintessence2. Farewell3. Libertate 2008 1. Pride of Baltimore II2. Lady Maryland3. A. J. Meerwald 1. Heron2. Adventurer 563. Prom Queen 1. Sally B2. Mistress 583. Dove II 1. Malabar II2. Green Dragon3. Windfall 2009 1. Lady Maryland2. Pride of Baltimore II3. Virginia 1. Prom Queen2. Woodwind3. Juno 1. Adventurer 652. One World3. Sally B 1. Green Dragon2. Susan B Merryman3. Quintessence 2010 1. Summerwind2. Pride of Baltimore II3. Lynx 1. Adventurer 562. Prom Queen3. Woodwind 1. Sally B2. Russamee3. Martha White 1. Quintessence2. Rip Hudner3. Farewell 2017 1. Virginia2. Lady Maryland 3. Pride of Baltimore II 1. Summerwind 782. Woodwind3. Brilliant 1. Sally B2. Tom Bombadil3. Libertate 1. Renegade2. Flower of Caithness3. Norfolk Rebel 2018 1. Sultana2. Columbia 3. Lady Maryland 1. Hindu 2. Woodwind3. Wolfhound 1. Libertate2. Sally B3. Tom Bombadil 1. Sea Hawk2. Norfolk Rebel3. Flower of Caithness

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