Fri–Sun 12 pm
Sultana Downrigging Weekend at Chestertown Marina
North America's biggest tall ships gathering turns Chestertown's harbor into a weekend of sails, ship tours and Friday fireworks.
The largest annual gathering of Tall Ships in North America fills Chestertown's waterfront alongside a bluegrass Music Village, ship tours, public sails and a Friday-night fireworks display over the harbor.
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Updated Friday, October 30, 2026 · real listings, pulled from 130+ sources and reviewed by a person.