Schooner Pride of Baltimore in Downtown Baltimore under sail

Pride in Downtown Baltimore

How to Watch the 2023 Great Chesapeake Bay Schooner Race

Sailors experience a certain form of nostalgia when the ships of the Great Chesapeake Bay Schooner Race commence their magnificent journey down the Bay, the white canvas and wooden hulls harkening back to the majesty of sail power and the beauty of nautical pursuit.

If Bay sailors do not have the opportunity to secure a berth (and a watch shift) and participate in the event, there are many chances to spectate from shore, or climb aboard while schooners are docked. The GCBSR organizers prioritize making it possible to get up close and personal with the incredible fleet, creating opportunities that do not come along often.

Ships will be docking at Anchorage Marina in Baltimore beginning Monday, Oct. 2, and the public is invited to come down and view the ships before they embark on their trek south. A Parade of Sail will commence around 4:30 p.m. on October 4, with schooners sailing from Anchorage Marina to Baltimore’s Inner Harbor and back to Canton. The best spectating can be done from Baltimore’s waterfront parks in Canton, Fells Point, the Inner Harbor, and Federal Hill.

Pride of Baltimore II running under full sail in the Great Chesapeake Bay Schooner Race. Photo by Jefferson Holland

The fleet will depart from the dock early in the morning on Thursday, October 5, making their way down to Annapolis where the start line will be positioned. Unlike prior years, when the start was close enough to Annapolis Harbor to allow for spectating off the Naval Academy seawall, the start line will be pushed off Hackett’s Point near shoal buoy G1. To best witness the start, contact your friends with boats and get out on the water yourself.

Once again this year, the Chesapeake Bay buyboat Nellie Crockett will serve as committee boat. Schooners have two course options, either 83 or 118 nautical miles in total. The first warning signals will be issued at noon, with all schooners racing by 1 p.m. All of this is weather dependent, however. But there is reason to be optimistic.

“It looks like the weather gods are working in our favor,” says Nan Nawrocki, executive director of Sail Baltimore and one of the architects of this year’s race. “The race is always contingent upon the wind, and we’ve had a few hurricanes over the years.”

After finishing, schooners will be docking at Freemason Harbor on the Elizabeth River in Norfolk. A pig and oyster roast is planned for Saturday afternoon, followed by a Schooner Social in the evening and a sea shanty singalong to close out the night. All events will take place at Freemason Harbor.

The Great Chesapeake Bay Schooner Race celebrates the mission of “racing to save the Bay.” Educational opportunities are offered to children living on the Chesapeake about ecological stewardship and historical significance. But the race also calls us to remember a time of greater relationship between sailors and the sea. To support the mission and learn more about this year’s participants, visit