Great Chesapeake Bay Schooner Race - WOODWIND
Date: 12 October 2026
Location: Start off Annapolis, finish Norfolk, Virginia (Chesapeake Bay), Annapolis, 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.
View this event on the World Sailing Day map
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Sailing nearby
Planning to attend? These clubs, marinas, schools and other sailing places are close to Annapolis and worth a visit while you are in the area:
- Annapolis City Marina — Marinas, Annapolis, United States
- Annapolis Fishing Charters — Yacht & Sailing Charters, Annapolis, United States
- Annapolis Flotilla 23-01 — Sea Scout Groups, Annapolis, United States
- Annapolis Maritime Museum — Maritime Museums, Annapolis, United States
- Annapolis Sailing School — Sailing Schools, Annapolis, United States
- Annapolis Sailing School — Yacht Clubs, Annapolis, United States
- Annapolis Yacht Sales — Yacht Brokers, Annapolis, United States
- Chesapeake Sailing School — Sailing Schools, Annapolis, United States
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