March 4, 2024
Annapolis, US 57 F

EYC to host 10th Annual Wooden Sailboat Rendezvous & Race

Now in its 10th year, the popular Classic Wooden Sailboat Rendezvous & Race will continue its tradition of showcasing the history and elegance of classically designed wooden sailboats during the weekend of September 21-22.

Since its inception, the race has been hosted by the National Sailing Hall of Fame in conjunction with the Chesapeake Traditional Sailing Association (CTSA). But with the Sailing Hall of Fame’s recent move to Newport Rhode Island, the race organizers decided to join forces with their new hosts at the Eastport Yacht Club who welcomed them with open arms.

This fun gathering of classic wooden sailboats provides an informal opportunity for wooden sailboat enthusiasts to join together and compete in a low-key race against other wooden sailboats. The race is open to sailing vessels with an overall length on deck of less than sixty-five (65) feet, designed before 1970, and whose hull is built primarily of wood.

Many of the historic boats will be on display at the Annapolis City Docks on Saturday, September 21. The public is invited to come see these extraordinary boats in person, talk with the captains and will even have a chance to board some of the boats on display.

The race itself will take place the following day on Sunday, September 22 at 11:00am and will take place on the Severn River at the entrance to Annapolis Harbor (*weather permitting). The course is a pursuit style race meaning that the slowest boats will start first followed by the fastest, and the winner of each class will be determined by the length of time it took them to complete the course.

This event has grown each year, with boats ranging in size from 8-feet to 65-feet, and coming from as far as Canada and Australia. In 2017, sailors from Australia’s oldest open boat sailing club, the Sydney Flying Squadron, brought their own fleet of historical 18-foot skiffs to Annapolis, to participate.

For more information or to register your boat (registration ends on September 19, 2019), please visit the official race Facebook page at

If you are interested in participating in the race but do not own or have access to a classic wooden sailboat, the Schooner Woodwinds invite you to participate aboard their boats which will be racing in the “Spirit of Tradition Class.” Tickets prices, which are $90 for adults and $54 for children, include a 3.5 hour cruise, bagged lunch, soft drinks, bottled water, and tax. There will also be a cash bar available that will include a selection of craft beer and wine. For more information about the Schooner Woodwinds’ Classic Wooden Sailboat Rendezvous & Race Cruise and/or to purchase tickets, please call 410-263-7837 or go to

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