Chesapeake Bay Sailors Race Into a Spectacular Season

Autumn Is the BEST for Sailboat Racing on the Chesapeake Bay

Don’t try to make non-sailing weekend plans with a Chesapeake racing sailor from now through Halloween! Regional racers take full advantage of the windy days, lower humidity, and warm water that make autumn a favorite season for those who like to sail fast.

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The J/30 North American Championships return to Annapolis on the Chesapeake Bay this fall. Photo by Will Keyworth

Starting with Labor Day—which may kick off “fall” yet still feels summery—racers enjoy holiday weekend favorites, such as the Labor Day Invitational (August 31) and Fishing Bay Yacht Club’s (FBYC) Stingray Point Regatta (August 30 – September 1). Racing sailors have events to choose from September through November, from distance races, such as the Navy Fall Race to Cambridge (in lieu of the annual Fall Oxford Race due to a scheduling conflict, September 7), to fall series weekends up and down the Bay.

Autumn racing events culminate in championships, particularly for one-design sailors. There are more such events on the Chesapeake this upcoming season than we’ve seen since the pandemic.

To get the party started, the J/30 North American Championship Regatta returns to Annapolis (September 12-15) out of Eastport Yacht Club. At print time, 14 J/30s had already registered, including local rock stars in the 40-year-old sailing class and registrants from Oswego, NY, and New Orleands, LA.

Hampton Yacht Club will host two events of note, beginning with the Shark Class Nationals (September 17-19) and followed by the 505 East Coast Championships (September 20-22).

Annapolis Yacht Club (AYC) will once again host the Cal 25 National Championship Regatta (September 27-29).

Back down on the Southern Bay, FBYC will host an annual favorite, which draws a slew of Annapolis dinghy sailors to Deltaville, VA, the Chesapeake Bay ILCA Masters Championship Regatta (October 5-6).

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Autumn is an incredible season to race sailboats on the Chesapeake as these J/boats show at the J/22 and J/24 East Coast Championships. Photo by Ted Morgan

In Annapolis, the weekend following the Sailboat Show, Severn Sailing Association will welcome J/22 and J/24 East Coast Championship competitors (October 18-20). The same weekend, the J/105 Chesapeake Bay Championships is set to unfold out of AYC.

The last championship event is an exciting one: the J/22 World Championship Regatta (October 22-26) will take place at EYC. At print time, 48 boats had registered from all over the map from the Chesapeake to Colorado and from Quebec to Jamaica.

After the J/22 Worlds, there are a few more regattas, such as the EYC Fall Brawl and the HYC Fall Fling (November 5-6), and then, dare we say it, frostbite racing season!

If we’ve missed your club’s major event, email [email protected] for inclusion in our calendar and possible post-race coverage.