2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 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!

Sultana Downrigging Tall Ship Sails

The Sultana Education Foundation’s Downrigging  offers opportunities to sail the Chester River on your choice of 9 historic tall ships.

Chestertown Marina

About This EventThe Sultana Education Foundation’s Downrigging Weekend offers multiple opportunities to sail the Chester River on your choice of nine historic sailing vessels. Each Downrigging sail is 2.5 hours long and departs and returns from the Chestertown Marina at 207 S. Water St. in Chestertown. No previous experience is required to participate, but it’s important that participants dress appropriately for the weather. Please see the FAQ section on the Downrigging website (<a href="http://www.downrigging.org" title="http://www.downrigging.org" target="_blank" data-msys-clicktrack="0" rel="nofollow noopener noreferrer">www.downrigging.org</a>). Children under 5 years of age are not permitted. Please see additional information, including refund policy, under Terms and Conditions.

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2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm

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Chestertown Marina

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2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm

Good to know

Location

Chestertown Marina

How do you want to get there?

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