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You might be aware Annapolis is called America’s Sailing Capital. But did you know that if you visit this beautiful seaside city on a Wednesday night this summer, you can participate in an exciting sailboat race?

Annapolis’ Wednesday Night Sailboat Races have been a beloved summer tradition for the locals since the 1960s. Annapolitans take the competition seriously, but in a friendly way, and every event is supervised by the Annapolis Yacht Club (“AYC”). 

The races have created Annapolis’ unique definition of “Hump Day” during summer. Many locals embrace having the middle of their work weeks disrupted by this nautical sporting event.

The Race

Over 125 sailboats in 15 classes race following U.S. Sailing Association rules enforced by an AYC judge. Fans can get a close look of the start and finish from bars and restaurants on the Severn River, the Spa Creek Drawbridge, and boats along the course.
The sailboats maneuver around the mouth of Spa Creek and try to time crossing the starting line right after the starting gun. They sail around several markers in the bay, pass beneath the Spa Creek Drawbridge, and hurry to get to the finish line in front of the Annapolis Yacht Club clubhouse.

How to Participate

The skippers and their crews range from amateur to professional. If you want to participate, book a cruise on either the Woodwind or Woodwind II.

Both sailboats were specially designed to sail the Chesapeake Bay and are reminiscent of the classic, speedy schooners that were classed as “yachts” early in the 20th century.

When appropriate, you and your loved one can help steer and crew one of these sailboats to victory.

For More Information: Annapolis Wednesday Night Races on the Woodwinds

Your Inn Near the Wednesday Sailboat Races

Your racing sailboat is just a short walk from Gibson’s Lodgings, a historic inn located in downtown Annapolis offering superb accommodations and free parking for guests.

Gibson’s three houses host 20 fully-furnished guest rooms, with three 19th-century parlors, a dining room, conference room, and beautiful central courtyard. See the photos of our beautiful rooms by clicking on the link for each house below.

Berman House
Lauer House
Patterson House

Call us to reserve your 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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