The 4.4-mile Great Chesapeake Bay Swim (GCBS) is an annual event that is usually scheduled for the second Sunday of June.  The race begins from the shore of Sandy Point State Park, which is about 5 miles northeast of Annapolis, extends eastward between the two spans of the Chesapeake Bay Bridges (U.S. Highway 50), and finishes on Kent Island immediately south of the Bridges’ eastern-shore causeway.

A 1-Mile Chesapeake Bay Challenge swim consists of a course starting and ending at the sandy beach adjacent to the Bay Bridge Marina on the eastern shore immediately south of the Bay Bridges.  The event is coincidental with the GCBS, and the two events start approximately the same time at the different ends of the Bay Bridges.

Entry to the 4.4-mile and 1-mile events are managed by RunSignup.