Downrigging Weekend Sails--Friday, October 31, 2:30pm-5:00pm

It all started back in 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 Sultana Downrigging was born.

Almost two decades later, Sultana Downrigging has grown to be one of the largest Tall Ship gatherings in the country which beginning in 2019 was combined with a major bluegrass festival. Visitors can expect to see a waterfront packed with ships and wooden boats; three days of performances by the region’s best bluegrass musicians; great food in the festival’s waterfront village, lectures by nationally recognized authors; activities for children; opportunities to sail on the visiting Tall Ships; and the chance to spend the weekend in Chestertown – one of America’s best-preserved historic seaports. Don’t miss it!