Chestertown, Maryland’s 2016 Downrigging Festival was a beautiful fall weekend for celebrating the most beautiful wooden boats on the Chesapeake Bay. Whether local ladies like the Sultana or the Elsworth, city girls like the Pride of Baltimore or the Sigsbee, or vessels from further afield like the Kalmar Nyckel, the ships are stacked up on the dock sometimes two-deep to allow visitors from around the country the chance to see and sail on these magnificent craft. 

It’s an event that marks the end of the tall ship season on the Chesapeake- and afterwards, many of the buyboats, bugeyes, schooners and clippers return to their home port to be unrigged, hauled and worked on over the winter. With fireworks, bluegrass, and some stately trips down the Chester River, thousands of people celebrate the year’s last hurrah for these charming watercraft. Hulls gleaming and flags standing proud in a warm fall breeze, they are reminders of a time not so distant when these ships were the Bay’s most essential connection between small Chesapeake towns and a vast maritime world. 

It’s a past worth celebrating- and a beautiful one, at that.

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