Classic Wooden Sailboat Race & Rendezvous Celebrates 10 Years

September 21-22 in Annapolis, MD

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 in Annapolis

Photo by Shannon Hibberd
Photo by Shannon Hibberd

Since it's inception, the race has been hosted by the National Sailing Hall of Fame (NSHOF) in conjunction with the Chesapeake Traditional Sailing Association (CTSA). But with NSHOF’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 65 feet, designed before 1970, with a hull built primarily of wood.

Photo by Craig Ligibel
Photo by Craig Ligibel

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 board some of the boats on display. 

The race will take place the following day on Sunday, September 22 at 11 a.m. and will take place on the Severn River at the entrance to Annapolis Harbor. The race is pursuit-style, 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.

Photo by Shannon Hibberd
Photo by Shannon Hibberd

This event has grown each year, with boats ranging in size from eight to 65 feet, coming from as far as Canada and Australia. 

For more information or to register your boat by September 19, visit the official race Facebook page at facebook.com/classicwoodensailboatrace.

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.” (Find details at schoonerwoodwind.com).