"Volunteer" sailboat, Calvert Marine Museum, Solomons, Maryland, April 2018. Photo by Diane F. Evartt.

[photo, Sailboats, Back Creek, Annapolis, Maryland] In the Chesapeake Bay area, boating is a favorite pastime, and Annapolis has long been known as America's Sailing Capital. In December 2005, the National Sailing Hall of Fame was founded in Annapolis. In 2019, the Hall moved to Newport, Rhode Island, where its new Sailing Museum opened on May 10, 2022.

The Annapolis Yacht Club will host a Spring Race from Annapolis to Oxford on May 11, 2024, an Annual Regatta on July 27-28, 2024, and a Fall Race from Annapolis to Solomons in September 2024. 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 3-6, 2024, while the next Sailboat Show will be held on October 10-14, 2024.

Sailboats, Back Creek, Annapolis, Maryland, October 2008. Photo by Diane F. Evartt.

[photo, Sailboats at Inner Harbor, Baltimore, Maryland] The Mid-Atlantic's largest Spring boat show, the Bay Bridge Boat Show in Stevensville, as well as the Annapolis Spring Sailboat Show, are held each April. The Bay Bridge Boat Show and the Annapolis Spring Sailboat Show will next take place in April 2025.

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 47th running of the race will be held on August 2-3, 2024.

Sailboats at Inner Harbor, Baltimore, Maryland, August 2001. Photo by Diane F. Evartt.

[photo, Sailboat, Little Round Bay, Crownsville, Maryland] Eastern Shore boat races also start at Cambridge, where the Choptank Heritage Skipjack Race has been held each September since 1997. It is next scheduled for September 21, 2024. From Rock Hall on the upper Eastern Shore, regattas are sponsored in the summer.

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 on September 2, 2024.

Sailboat, Little Round Bay, Crownsville, Maryland, September 2017. Photo by Diane F. Evartt.

[photo, Sailboat on Severn River, Annapolis, Maryland] Since 1989, the Great Chesapeake Bay Schooner Race has sped from Fells Point in Baltimore to Portsmith, Virginia, each October. The next race is scheduled to run October 2-6, 2024.

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.

[photo, Sailboats, Back Creek, Annapolis, Maryland] Located on the St. Mary's River with access to the Chesapeake Bay, St. Mary's College of Maryland locally competes against teams from the U.S. Naval Academy and the U.S. Merchant Marine Academy.

Sailboats, Back Creek, Annapolis, Maryland, October 2008. Photo by Diane F. Evartt.

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