The Annapolis Yacht Club will host a Spring Race from Annapolis to Oxford in May 2025, an Annual Regatta in July 2025, and a Fall Race from Annapolis to Solomons in September 2025. The Club also sponsors the Annapolis to Newport Race, a 475-mile competition which is held every two years. The next race will be held on June 6-7, 2025.
Each October, Annapolis hosts the United States Powerboat Show and the United States Sailboat Show, the two oldest and largest shows of their kind in the nation. The next Powerboat Show will take place on October 2-5, 2025, while the next Sailboat Show will be held on October 9-13, 2025.
Sailboats, Back Creek, Annapolis, Maryland, October 2008. Photo by Diane F. Evartt.
Starting in Annapolis, the Annual Governor's Cup Yacht Race is a 70-mile long overnight distance race from Annapolis to St. Mary's City. Competitors race down Chesapeake Bay, turning up the Potomac River to the St. Mary's River in southern Maryland. The 48th running of the race will be held in August 2025.
Sailboats at Inner Harbor, Baltimore, Maryland, August 2001. Photo by Diane F. Evartt.
For fifty years, Deal Island off Somerset County (also on the Eastern Shore) has been home to the Annual Skipjack Race and Festival. Over Labor Day weekend, the Race next will be held in September 2025.
Sailboat, Little Round Bay, Crownsville, Maryland, September 2017. Photo by Diane F. Evartt.
Competitive sailboat racing boasts many participants throughout the Chesapeake Bay area. Year-round, Maryland's local yacht clubs host racing series and regattas. Numerous sailing schools train future racing champions and recreational sailors.
Since 1991, St. Mary's College of Maryland, competing in the Mid-Atlantic Intercollegiate Sailing Association, has captured twelve national championship titles, including two in 2007. In 2009, the St. Mary's Seahawks beat Yale University to win the Inter-Collegiate Sailing Association/Gill Coed Dinghy National Championship for the third time in school history.
Sailboat on Severn River, Annapolis, Maryland, April 2001. Photo by Diane F. Evartt.
Sailboats, Back Creek, Annapolis, Maryland, October 2008. Photo by Diane F. Evartt.
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