The Great Chesapeake Bay Schooner Race: Oct 15-21, 2019

30 Schooners to Race Down The Bay

Chills up the spine… Any sailor who’s seen the spectacle gets the chills when first spying 30 schooners lining up for the start of the Great Chesapeake Bay Schooner Race (GCBSR). We don’t take it for granted here in Chesapeake country: seeing three dozen schooners from 12- to 125-feet long, sailing in one place with the Bay Bridge as a backdrop on a beautiful mid-October day.


In any sailing town around the world you can see shiny new race boats, but to see such old-fashioned lines of schooner hulls, carved wooden figureheads and bowsprits, the spectacular webs of rigging and many sails (foresails, staysails, fishermen, topsails), and the devoted schooner sailors who heave and ho; it’s breathtaking to witness.

The weeklong GCBSR festival starts October 15 with a parade and other events including educational tours in Baltimore; moves south to Annapolis for the start of the 120-mile race down the Chesapeake; and ends with special events in historic Portsmouth, VA. This year’s edition runs through October 21, with the official race start happening off Annapolis Thursday, October 17 at noon, which is in itself a well-loved spectator event.

Great Chesapeake Bay Schooner Race
A spectacular day for schooner racing at the GCBSR 2018. Photo by Eric Moseson

The GCBSR is much more than just a race. Among the event’s missions are: to promote awareness of the Chesapeake Bay’s heritage, to encourage preservation of the Bay’s resources, to support Chesapeake Bay education and clean-up efforts, to bring historic schooners to the Bay, and to encourage schooner sailing and preservation. With this in mind, Wednesday and Saturday of GCBSR week (in Baltimore and Portsmouth respectively) are for public outreach and education. Find the full schedule of events at

GCBSR Photo by Will Keyworth
GCBSR photo by Will Keyworth

At print time, among the entries for the 2019 GCBSR are: A J Meerwald (115 feet), Adventure (41.5 feet), Adventurer (56 feet), Apella (54 feet), Bonny Rover (64 feet), Celebration (39.5 feet), Delphinus (26 feet), Farewell (47 feet), Flower of Caithness (54 feet), Lady Maryland (104 feet), Libertate (54 feet), Liberté (45 feet), Liberty Clipper (125 feet), Lion of Baltimore (12.5 feet), Lynx, Mistress (77 feet), Moonbeam, Norfolk Rebel (59 feet),  North Wind (75 feet), Ondine (50 feet), Pride of Baltimore II (95 feet), Sally B (60 feet), Sea Hawk (56 feet), Shanty (50 feet), Sultana (97 feet), Summer Wind (48 feet), True Love, Virginia (126 feet), Windfall II (39.5 feet), and Woodwind (74 feet). 


Learn more at