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Classic Wooden Boat Regatta

September 10, 2023 @ 10:30 am - 2:30 pm

Great Chesapeake Bay Schooner Race on Schooner Woodwind

Participate in the Classic Wooden Boat Regatta. The Woodwinds’ have been invited to participate in the race in the “Spirit of Tradition Class”.

The course is a short race with laps to make the sailing close and it takes place in the Severn River. It can be up to a 3 lap race with a pursuit style race. Each boat has a rating, and by the rating they will get a start time. The pursuit style race challenges the competitors to sail through the other race boats to win the regatta. This will be an amazing trip for photography (hint B&W or sepia tone) of these older, gorgeous boats.

This is going to be a fun, challenging race! Join the crew!

After the racing, all participants aboard both schooners are welcome at the Eastport Yacht Club, who is hosting the event. This is the best view of Annapolis, other than onboard the Woodwinds. More details will be given aboard. (Party is pay your own.)


  • Departs Annapolis at 10:30 am and returns to Annapolis at 2:30pm.
  • Includes Soft drinks and tax.
  • Our bar includes a selection of Craft Beer, Wine & Bubbly available for purchase! And it’s Sunday Funday, so Bloody Marys, Screwdrivers, Mimosas and Glasses of Bubbly will be offered, too.

Discounted price does not include lunch feel free to bring an individually packaged lunch to enjoy aboard. No buffets allowed.


September 10, 2023
10:30 am - 2:30 pm
Event Category:
Schooner Woodwind