Tall ships and top bluegrass bands from across the East Coast are setting course for Chestertown as the Sultana Education Foundation (SEF) prepares to host its annual Downrigging Weekend Festival over Halloween Weekend. Celebrated as the only “Tall Ships & Bluegrass” festival in the world—and the largest annual public sailing event in the United States—Downrigging draws tens of thousands of visitors and stands out as one of the Chesapeake Bay’s signature waterfront celebrations. Proceeds from the festival benefit SEF’s award-winning environmental literacy programs and support the participating nonprofit tall ships.
Over the three-day festival, more than 1,100 guests will set sail on the Chester River aboard a fleet of historic tall ships, with Chestertown’s own schooner SULTANA sailing alongside AJ MEERWALD, GODSPEED, KALMAR NYCKEL, LADY MARYLAND, LYNX, MARYLAND DOVE, PRIDE OF BALTIMORE II, and SIGSBEE. The fleet will embark on four public sails, with a limited number of tickets still available. Visitors can also enjoy free daily deck tours, evening ship illuminations, and a fireworks display over Chestertown’s historic harbor on Friday at 8:15 p.m. The tall ship fleet will be complemented by smaller vessels and exhibits from the Antique and Classic Boat Society, Traditional Small Craft Association, Mystic Seaport Museum, American Schooner Association, and Silver Heel Foundation.
Onshore, the Downrigging Music Village will feature an exciting lineup of bluegrass talent, featuring Wicked Sycamore, Tim and Savannah Finch, Serene Green, The High and Wides, Level Best, Unspoken Tradition, Missy Raines (Grammy nominee, ten-time IBMA award winner), Danny Paisley (four-time IBMA Vocalist of the Year), Flatland Drive, Midshore Voices United, and the U.S. Navy’s Bluegrass Band, Country Current. The Village will also host a Halloween costume party on Friday, offering chances to win free drink vouchers and $500 in prizes. Music tickets range from $25–$60, and entry on Sunday is free.
Downrigging 2025 also features maritime experiences and activities for all ages, including book talks by Dave Gendell and Thomas Guay, maritime art by Marc Castelli, interactive lectures on SULTANA and African American maritime history by Chris Cerino, a presentation on the Great Chesapeake Bay Schooner Race by Duncan Hood, and a model boat and ship exhibit by the Washington Ship Model Society. Additional events include a Thursday night preview concert with Sombarkin’ at Sumner Hall, a Downrigging yoga class by Slack Tide Yoga, children’s crafts with RiverArts, a children’s book reading by Letitia B. Burton, and a Downrigging Petting Zoo.
For tickets and a full schedule of events, visit www.downrigging.org.
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