The Governor’s Cup Yacht Race, the oldest premier overnight race on the Chesapeake Bay, will take place August 1-2, 2025. With a 68.6-nautical-mile main race course from Annapolis, three other race routes are available to area sailors, all finishing at St. Mary’s College of Maryland (SMCM). The entire community is welcome to join in the fun, as a day full of activities are planned on the College’s waterfront on Saturday, August 2, featuring food, music and fun for the entire family.