The race—held in October of each year—begins just south of the Chesapeake Bay Bridge near Annapolis, Maryland, and ends at Thimble Shoal Light north of the Hampton Roads channel, covering 127 nautical miles (146 mi; 235 km).
[1][2] Pre- and post-race activities take place in Baltimore, Maryland, and Portsmouth, Virginia, respectively.
Proceeds from the race support Chesapeake Bay education and preservation projects.
[3] The current time to beat is 11 hours, 1 minutes, 41 seconds and was set in 2017 by the schooner Virginia.
[4][5] The previous time to beat was 11 hours, 18 minutes, 53 seconds and was set in 2007 by the schooner Virginia.