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Annapolis has a few nicknames involving sailing: “America’s Sailing Capital” and “Sailing Capital of the World”. You will find out why if you happen to be in the city during the middle of the week. You cannot miss the local summer tradition called the Wednesday Night Sailboat Races. What used to be a casual happening that was established in 1960s is now a serious weekly event overseen by the Annapolis Yacht Club (AYC).

Inspired by a Rhode Island summer sailing competition, the late Gaither Schott, an AYC Commodore, organized the races during the summer of 1959. They were much more informal then than they are now. No trophies or points awaited the winners; only a picnic at the end of the day and friendly pats on the back.

Many American maritime towns and cities hold weeknight regattas, but Annapolis’ Wednesday Night Sailboat Races has a special flavor of its own. The event seems to have given Annapolis locals a new definition for “Hump Day” by disrupting the middle of their work week with a thoroughly enjoyable interruption.

More than 125 sailboats categorized in 15 classes compete under U.S. Sailing Association rules. They are cheered on by partying spectators from restaurants and bars overlooking the Severn River, the Spa Creek Drawbridge, and from boats that sometimes get in the way. A judge from the AYC watches over the event, and just like America’s Cup, there are occasionally protests over broken rules.

The skill levels of sailors and their crews range from amateur to professional. Many competitors are Annapolitans, but those who aren’t are also welcome. Eager prospective deck hands are often invited via social media or on the spot by skippers to fill available spots of a sailboat’s crew.

Every Wednesday evening from April to early September, their sailboats jockey at the mouth of Spa Creek to cross the starting line just before the bang of the starter’s gun. They round several markers on the Chesapeake Bay, pass under the Spa Creek Drawbridge, and race to the finish line at the clubhouse of the Annapolis Yacht Club.

The Wednesday Night Sailboat Races are just a short walk from Gibson’s Lodgings, a historic inn located in downtown Annapolis. Call us to reserve your bed & breakfast room at our toll free number 877-330-0057. We’ll be very happy to serve you and your family throughout the year.

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