Downrigging Weekend annually draws tall ship lovers from around the Chesapeake watershed to tiny Chestertown, Maryland. The waterfront, normally home just to the Schooner Sultana and a handful of workboats-turned-classrooms, now bristles with masts and rigging of visiting vessels from petite to behemoth. Each different ship, whether schooner, workboat or pleasure yacht, is a beautiful example of its type, and during the day, the docks teem with passengers eager to board and sail down the Chester River’s wide bends on these breathtaking boats. Even decidedly landlubbing-types can’t help but slow down to ogle the brilliantly-painted figureheads or glossy brightwork the gives a brief glimpse at the beauty and glamour of the Chesapeake’s seafaring past.

All photos by author.