Great Chesapeake Bay Schooner Race - WOODWIND

Date: 12 October 2026

Location: Chesapeake Bay, Annapolis to Norfolk, United States

Organizer: 59º North

The Great Chesapeake Bay Schooner Race sends a fleet of twenty to thirty schooners racing down the Chesapeake to Norfolk, Virginia, a tradition now more than three decades old. For 2026, offshore sailing outfit 59 North is offering crew berths aboard Woodwind, an Annapolis schooner with a strong record in the race over its 30-plus years. Crew join in Annapolis on Monday, October 12 for preparation and provisioning, then sail to Baltimore for pre-race training and the Inner Harbor Parade of Sail before racing the length of the bay. The week ends in Norfolk with the awards ceremony, oyster roast and a sea shanty singalong. This is participation, not passage-making tourism: crew work every aspect of the boat from prep to finish. Racing a gaff-rigged schooner hard downwind through a fall night on the Chesapeake is a rare thing to get to do, and that is the sell.

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