ANNAPOLIS, Md. — The Governor’s Cup Yacht Race, the Chesapeake Bay’s oldest premier overnight sailing event, is set for August 1-2, 2025, with a 68.6-nautical-mile main course from Annapolis to St. Mary’s College of Maryland (SMCM). Three additional race routes—Solomons Island, Potomac, and Fishing Bay—offer options for sailors, all concluding at SMCM’s waterfront, where community festivities await on August 2.
“The Governor’s Cup Yacht Race, started by three St. Mary’s College students in the 1970s, has become a time-honored tradition for Chesapeake Bay sailors,” said Rick Loheed, SMCM’s associate director of waterfront activities and race director since 2008. “We’re looking forward to as many as 100 boats competing in this year’s Governor’s Cup Yacht Race, and a lot of fun activities for racers and the community alike.”
Sailors can choose from multiple race classes, starting from Annapolis, Solomons Island in Calvert County, Dahlgren, Virginia (Potomac Leg), or the Piankatank River off Deltaville, Virginia (Fishing Bay Leg). The Governor’s Cup Yacht Race attracts a diverse fleet, with up to 100 boats expected to compete in 2025, showcasing the event’s enduring appeal.
The community is invited to join the festivities at SMCM’s Teddy Turner Waterfront (47498 Trinity Church Rd) on August 2. Events begin Friday, August 1, at 7 p.m. with the Baltimore Symphony Orchestra’s “Summer Serenades” at the Nancy R. & Norton T. Dodge Performing Arts Center. This “pay-what-you-wish” concert, part of the BSO’s “Music for Maryland,” requires advance booking due to high demand.
On Saturday, the Governor’s Cup Yacht Race festivities continue from 8 a.m. to 7 p.m. with live music from three bands, an all-you-can-eat breakfast at Trinity Episcopal Church Parish Hall from 6 a.m. to noon, and food trucks on-site from noon to 8 p.m. A bar service, offering signature cocktails and other beverages, will operate from 8 a.m. to 8 p.m. These activities create a vibrant, family-friendly atmosphere for racers and visitors.
The Governor’s Cup Yacht Race combines competitive sailing with community engagement, drawing participants and spectators to SMCM’s scenic waterfront. For race entry details, shoreside amenities, and event schedules, visit. The event underscores the Chesapeake Bay’s rich maritime heritage and SMCM’s role in fostering regional traditions.
