This Halloween weekend, imagine yourself sailing down the Chester River on a historic tall ship, then listening to bluegrass music along the waterfront as fireworks fill the sky. At the Sultana Downrigging Festival in Chestertown, Maryland, from Oct. 31-Nov. 2, thousands will attend to do just that. This three-day celebration of tall ships and bluegrass music will include public sails, concerts, lectures, art exhibits, and tall ship tours: a veritable cornucopia of Chesapeake maritime culture.
“It’s the largest public sailing event in North America,” says Drew McMullen, President of Sultana Education Foundation, which holds the festival each year. Named for the task of lowering a schooner’s sails at the end of the summer, the Downrigging Festival unites tall ships and bluegrass music to celebrate the end of the sailing season.
The festival began in 2002, when Sultana Education hosted the Pride of Baltimore II to sail with their replica schooner Sultana on the Chester River. This year, Chestertown will see a fleet of nine tall ships venture out on the Chester River four times to take over 1,000 people sailing. In addition to the tall ships are a plethora of smaller wooden sailing vessels, turning the river into an old-time nautical spectacle.
“[Chestertown] is one of the few places in the entire Bay with enough deepwater dock space for these ships,” says McMullen. “There’s really nowhere else you can do this. It’s also a great town for this festival, because it’s a colonial-era town that hit its peak around the American Revolution.” Today, it has around the same population and scale as it did then. “So when you put these boats in the waterfront, it kind of looks like it did 250 years ago.”
But it’s more than just the town that brings history to life: two replicas of important 17th-century tall ships, the Jamestown Godspeed and the Maryland Dove, will be present in this year’s fleet. The original Godspeed set sail from London in 1606, one of three ships that began the Virginia Colony. Her landing point in 1607 became Jamestown, the first permanent English settlement in North America.
The Dove helped found the Maryland Colony in 1634, sailing across the Atlantic from the Isle of Wight. She survived a storm in the English Channel and, three months later, sailed up the Chesapeake to the Potomac River, where she landed on St. Clements Island. The modern-day Dove, launched in 2022, replicates the design of this founding ship and represents an important piece of Maryland history.
“People enjoy these ships because they enjoy seeing a piece of technology that is both quite complex and physically relatable,” says McMullen. “You can actually see how the thing works and understand it. It’s a throwback to a world that you don’t get to see very often, and you really can get a glimpse of it here.”
Along with the tall ships, which offer ticketed river sails and free tours throughout the weekend, the Downrigging Festival will be full of bluegrass music: more than ten bands will play in a waterfront Music Village. On Friday night, they’ll throw a Halloween party with a costume contest and fireworks. And, on both Friday and Saturday evening, the nine tall ships will be illuminated on the river after dark— a spectacle that draws photographers to the riverfront from all over Maryland.
In town, there will be free events, exhibits, and lectures about tall ships and Chesapeake Bay history, including a model boat exhibit and an exploration of Lawrence Nature Preserve. On Saturday, Annapolis author Dave Gendell will give a talk about his recent book, The Last Days of the Schooner America, an adventure-filled history of the first racing yacht to win the America’s Cup trophy.
All proceeds from the festival benefit Sultana Education Foundation, a nonprofit organization working to provide environmental literacy to Maryland public schools. “For Sultana, Downrigging is just one day of the year,” says McMullen. “But for 365 days, we are dedicated to educating students about the Chesapeake Bay.”
Tickets for the tall ship sails and music village are available on the festival website, and are selling fast. Ship tours and all other events and exhibits in town are free.
