It all started back in November, 2001, when the newly launched schooner SULTANA and the PRIDE OF BALTIMORE II, took a casual sail together on the Chester River the weekend before both vessels “downrigged” for the winter. The combination of a stiff breeze, the fall colors at their peak, and thousands of waterfowl flying overhead, made it a day few onboard either vessel would soon forget. “We’ll have to do this again next year,” remarked both Captains – and so Downrigging Weekend was born.

Now in its 18th year, Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival has evolved into one of the largest annual Tall Ship gatherings on the East Coast. Visitors to the festival can expect to see a waterfront packed with ships, schooners, and wooden boats; performances by world-class musicians; lectures by nationally recognized authors and filmmakers; plenty of opportunities to go sailing as part of a fleet of “Tall Ships”; and the chance to spend the weekend in Chestertown - one of America’s best preserved historic seaports.