Beginning on Friday, July 31 and ending Saturday, August 1 is the thirty-sixth Governor's Cup Yacht Race. The sailing race is anticipated each year as sailors compete overnight to navigate the Chesapeake from Annapolis to St. Mary's City.

Depending on the weather, yachtsmen have to deal with calm winds or storms, sailing through shipping lanes and hours of darkness and doubt. Even so, the yacht race is the oldest and longest overnight race on the Chesapeake Bay. The race begins in Annapolis, Maryland’s modern capital to St. Mary’s City, the first capital.

On Saturday after the competition is over, the sailors are treated to one of the premiere parties anywhere. There will be great live music, food and an awards ceremony. The Governor’s Cup finale begins at noon and ends at approximately 10 p.m.

After that, sailors pack up and wait another year to complete in Maryland most famous yacht race.