Tall Ships to Gather on the Chester River for Downrigging Weekend

According to the Sultana Education Foundation, the tall ships rendezvous known as Downrigging Weekend all started back in November 2001. 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.

Tall Ships Rendezvous in Chestertown, MD, each October for Downrigging Weekend. Photo by Al Schreitmueller

Since 2001, Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival has grown into one of the largest annual tall ship gatherings on the East Coast. Tall ships in attendance include: Kalmar Nyckel, Pride of Baltimore II, Lynx, A.J. Meerwald, Lady Maryland, Sultana, Elsworth, and Sigsbee. The Sultana, for which the weekend is named, is a reproduction of the 1768 namesake used by the British Royal Navy to enforce the notorious tea taxes in the years preceding the American Revolution. Built in Chestertown and launched in 2001, the new Sultana’s mission is to educate students of all ages about the history and ecology of the Chesapeake Bay. 

​​The fleet will be illuminated each night from 6:30 to 9:00 p.m. Photo by Eric Moseson

Visitors to the festival will have the chance to sail on the waters of the Chester River onboard their choice of eight of the visiting vessels. Tickets range in price from $25 to $55 per person; children under five years of age are not permitted to sail. There will be four sails throughout the weekend featuring the entire downrigging fleet. These ships are also available for free vessel tours (dockside) at set times during the festival. 

The festival also features a lighted boat parade down High Street October 27 at 6:45 p.m. There will be Dock Dogs competitions, a 5K Run/Walk at Wilmer Park, vintage boats and cars on display, live music, arts and exhibits, crab skiff races, and more. The fireworks show will take place Friday, October 27 at 7:30 p.m., and the fleet will be illuminated each night of the festival from 6:30 to 9 p.m. Learn more here.