Get your sea legs back! The tall ships are returning for Downrigging Festival—anchored to the bright, rhythm of bluegrass music.
Now in its 24th year, the festival began in 2001, when the Pride of Baltimore II joined the newly launched Sultana for a celebratory sail. “Everyone had such a good time that we did it again,” recalls Drew McMullen, Presiient of the Sultana Education Foundation. “Then we invited other boats, and then more boats—and eventually we had as many as we could.”
Over time, the celebration grew beyond the docks. “We wanted to make it bigger,” McMullen says. “That’s when we found Rousby and added a bluegrass festival. Now it’s the world’s only tall ships and bluegrass event.”
This year’s fleet brings back several longtime favorites—Pride of Baltimore II, Lady Maryland, Sigsbee, and AJ Meerwald—along with the Godspeed from Jamestown, visiting Chestertown for only the second time. “There just aren’t that many of these boats around,” McMullen says. “We work hard to bring the best, and they’re all nonprofits doing education work, just like us.”
The musical half of the festival began as an experiment. “Drew wanted to add music as a way to generate income,” says Rousby Quesenberry, Downrigging’s longtime music director. “At first, I laughed. I’ve been in this business long enough to know bluegrass isn’t exactly a cash cow.”
But what started modestly has grown into one of the strongest regional bluegrass gatherings on the East Coast. “We’re not just playing to tall-ship people anymore,” Quesenberry says. “We’ve converted some of them, and now we have our own audience.”
Each year, Quesenberry attends the International Bluegrass Music Association conference to scout new acts. “They have a gig fair—it’s like speed dating for bands,” he says. “This year, 18 groups pitched to play at Downrigging.”
The 2025 lineup features one of the festival’s best rosters yet. Friday night highlights Mid-Atlantic performers, including local favorites The High & Wides, who got their start in Chestertown. Saturday brings bands from Pennsylvania, Virginia, North Carolina, and Nashville, headlined by six-time Bass Player of the Year Missy Raines and her band, Allegheny, along with Danny Paisley, a multiple-time Male Vocalist of the Year. Sunday’s free Community Day features gospel, local favorites, and the Navy’s Country Current band—“They’ve played every Downrigging we’ve ever had,” Quesenberry notes.
Beyond the music and sails, McMullen says the weekend carries another. message. “Most of what Sultana does happens out of the public eye—we work with about 13,000 students a year on the Bay and in the field. Downrigging is our way to celebrate that work and share it with the wider community.” The event now supports roughly 15% of Sultana’s educational programs.
Next year’s festival will have special resonance: the 30th anniversary of the Sultana Foundation and the 25th anniversary of the ship’s launch. “We’re already thinking about how to tell that story through the 2026 event,” McMullin says.
And while the ticketed sails and concerts draw crowds, the weekend also offers plenty for free—dockside ship tours, lectures, art exhibits, fireworks, and cultural programs presented by local partners such as Sumner Hall, the Kent Cultural Alliance, the Bookplate, and the C.V. Starr Center.
For full schedules and ticket information, visit downrigging.org.
The video is approximately eight minutes in length.





