Sultana Downrigging Festival Does Not Disappoint Tall Ship Lovers

Tall Ships and Bluegrass at Sultana’s Downrigging Festival

At Sultana’s Downrigging Festival, October 28-30, thousands enjoyed the majesty of the largest collection of tall ships on the East Coast. They slurped local oysters, quaffed beer and soft drinks, gorged on cream of crab soup, learned about the legacy of Chesapeake sailing ships, and enjoyed some of the country’s best bluegrass, folk, and Americana music.


Thousands of sailors and tall ship enthusiasts gathered in Chestertown for the three-day Downrigging Festival. Photos by Craig Ligibel

It was a grand weekend to connect with Maryland’s nautical heritage as eight tall ships converged on the hamlet of Chestertown, Maryland, for the annual festival for tall ships and bluegrass.


Visitors were able to sail aboard the tall ships in the Chester River off the Chesapeake Bay.

The event was cancelled due to Covid-19 two years ago. It was staged to an enthusiastic crowd last year. This year’s event broke one-day attendance records on Saturday, October 29, as thousands of seafarers took advantage of a beautiful fall weekend to experience Chestertown’s signature event amid a kaleidoscope of fall colors heightened by a blustery wind that treated the lucky few who were able to garner sailing tickets to a beautiful sail-driven romp on the Chester River.


Sailors of all ages are enamoured with tall ships.

Tall ships on display and available for touring and sails included:

  • The Kalmar Nyckel, a recreation of the first colonial Swedish settlement ship to arrive in America.
  • The Sultana, a faithful reproduction of her 1768 namesake used by the British Navy to enforce the teas taxes in the years preceding the American Revolution.
  • The Virginia, a reproduction of the last all sail vessel built for the Virginia Pilots Association.
  • The Pride of Baltimore II, a reconstruction of an early 19th Century Baltimore Clipper, built in 1988 to the specifications of the original Pride of Baltimore which went down in a squall off the coast of Puerto Rico in 1986 with the loss of the captain and three crew members.
  • The Lynx, a square topsail schooner interprets a privateer schooner from the War of 1812.
  • The Sigsbee, a 1904 Chesapeake Bay skipjack.
  • The Godspeed, a reproduction of one of three ships that brought America’s first permanent English colonists to Virginia in 1607.
  • The Maryland Dove, newly launched in 2022, the Dove is a reconstruction of the original that sailed to the Maryland colony in 1634.


Raw oysters are a key attraction to fall festivals on the Chesapeake Bay.

Costumed interpreters and volunteers from the various organizations that represent the tall ships and other period vessels were on hand to explain the intricacies of sailing aboard one of these complex vessels.

Each ship took a number of passengers aboard for a two-hour sail on Friday, October 28, Saturday October 29, and Sunday October 30. Some passengers reported having obtained their coveted boarding passes more than 12 months in advance.


A Herreshoff Cat Ketch on display at Chestertown.

For those so inclined, the Chesapeake Chapter of the Antique and Classic Boat society had a number of power and sail vessels on display. Cocktail class boats as well as the log canoe Silver Heel were also represented.

The tall ships made their way to their respective home ports late Sunday, October 30 or early Monday morning, Oct. 31. Many of the ships will undergo annual maintenance over the winter. The Pride of Baltimore, for example, will have her 107-foot forward main mast pulled for inspection, a task that will entail a heavy-lift crane and a full crew to guide her spar to her winter maintenance shed.


Up or down, sailors appreciate the rigging in these classic sailing vessels.

For information of Downrigging 2023, go to downrigging.org/.

~Story and photos by Craig Ligibel