Tall Ships & Bluegrass: Sultana Downrigging Festival Returns

Sultana Education Foundation will once again host their annual Downrigging Festival in Chestertown, Md. from Oct. 29-31—but with a bluegrass twist this time. Named for the task of taking down a schooner’s sails at the summer’s conclusion, the festival celebrates the end of Sultana’s sailing season with community-wide activities.

The first official Downrigging Festival was held in 2002, in which Sultana hosted Pride of Baltimore II for a day of sailing on the Chester River. The pair of tall ships attracted a throng of tourists, inspiring expansion into a town-wide affair.

According to Chris Cerino, vice president at Sultana Education Foundation, additional events have been added to the festival each year to attract visitors beyond just sailing enthusiasts. This year’s event will feature over a dozen sailing ships and other vessels, and tours of the river will be offered throughout the weekend. Additionally, attendees can peruse Chestertown’s local businesses, many of which will be offering special programming for Downrigging weekend.

The Massoni Art Gallery, located on High Street, will feature local artist Marc Castelli, whose work captures the lives of Chesapeake Bay watermen and their workboats. A number of free lectures will be hosted throughout the town, including one on the history of whaling captains of color by former broadcasting executive Skip Finley.

For younger visitors, Sultana Education Foundation will hold Family Day at the Holt Center for Education on South Cross Street on Saturday. Little ones can interact with live animals, test their ship-building skills with a buoyancy challenge craft, or play lawn games in the parking lot. Admission to Family Day is free. 

The newest addition to Downrigging festivities is the full schedule of live music. This year’s event will feature 15 bluegrass bands, all performing throughout the weekend in the “Music Village”, set up at the Chestertown Marina.

The music component gives visitors an activity to do between sailing tours and attracts a new crowd to the Downrigging scene. Moreover, bluegrass music provides a perfect backdrop to a weekend of riverside activity.

“It’s a universal music—you just can’t hate bluegrass,” Cerino said. “It has such a broad appeal, and it just fills the air with a good vibe.”

Guests may purchase a ticket allowing them access to all the bands performing all weekend long. On Sunday, however, the music will be free to all.

This will be one of the largest events to take place in Chestertown since the start of the pandemic, and COVID-19 safety regulations are being enforced. Though nearly every event will take place outdoors, masks are strongly encouraged and will be required inside the Holt Center. Proof of vaccination or negative test is required to enter the whaling lecture and inside the Music Village. For health and safety guidelines, click here.

With regulations in place, Cerino is confident the event will run safely and smoothly.

“I think it’s going to be a great time,” he said. “And I’m just looking forward to getting everyone together to have fun again.”

-Alaina Perdon