Things to Do

To Do: Day Trip to St. Mary’s City for the Governor’s Cup

This year marks the 35th anniversary of the Governor’s Cup, an overnight sailing race from Annapolis to St. Mary’s City in Southern Maryland. The oldest and longest-running overnight race on the Chesapeake Bay, the Governor’s Cup begins this Friday, August 1 in Annapolis Harbor and ends Saturday, August 2 on the shores of St. Mary’s College of Maryland with a celebration that goes into the night.

If you’ve never been to this beautiful town on the banks of the St. Mary’s River, this weekend’s festivities are a great excuse to make the trip. Established by English colonists in 1634, St. Mary’s City was the capital of Maryland until 1695. Today the historic waterfront town is home to a collection of re-created 17th century buildings and a public museum of history and archeology.

The town’s other draw is St. Mary’s College, a liberal-arts school of about 2,000 students that was founded in 1840. On Saturday, the campus will come to life as it welcomes the sailors. Named one of sailing’s 10 best parties by Sailing World magazine, the Governor’s Cup will host two live bands—Joe Bachman and the Crew and the Nautical Wheelers—and serve local barbecue and seafood. The festivities begin on Saturday at Noon. For more information call 240-895-3039 or visit

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