Sailing to Join the Tall Ships at Downrigging Weekend

Ship tours and sailing opportunities

Downrigging Weekend  in Chestertown, MD, provides a full town festive experience with ship tours and sailing opportunities, street fairs, wonderful maritime art galleries, and great food, all in an historic setting especially suited to honor the fall season. You might say that they set the table for Thanksgiving. It is uniquely Chesapeake and always on my calendar, ” says SpinSheet contributing photographer Al Schreitmueller.

Sailing tall ships
See tall ships and other sailing vessels at Downrigging Weekend in Chestertown, MD. Photo by Michael Wooton

If you too love majestic vessels, ornate wooden bowsprits, sailors perched high on standing rigging, foresails, staysails, and topsails, then the Sultana Education Foundation’s Downrigging Weekend Festival, held this year October 29-31, might be the place for you. Chestertown and the Foundation, which are home to the Schooner Sultana, will play weekend hosts to a plethora of interesting vessels, both sail and motorized. Athough this unique fall festival began as a way to mark the final days of the tall ship sailing season, now, more than 20 years later, it is, as Schreitmueller says, a celebration of maritime history and the fall season.

“The Chesapeake Bay area provides an almost equal three months for each season’s variety,” Schreitmueller continues. “In fall we put away our swimwear and don our sweaters, pull the crab-pots, and tong for oysters. Fall marks geese migrating overhead, trees making their colorful displays, and waning angles of light turning the overlooked more golden. Like the trees celebrating their past season and looking to new leaves, the ships and schooners, built of wood, shed their sails and upper rigging in preparation for the winter season, for rest and restoration to begin again in spring renewed." 

More than Tall Ships

It is not just one of the largest annual tall ship gatherings in North America. The weekend offers live bluegrass music, lectures, exhibits, family activities, regional food and more. Proceeds benefit the Foundation’s environmental literacy programs, partner school program scholarships, and the other nonprofits that participate in the festival. In addition to the schooners and similar rigs, many motorized vessels and other traditional Bay boats will be demonstrated or on display. 

Each evening the tall ships will be illuminated, and the effect is simply stunning. To see an informal parade of sail, come down to the waterfront in the late afternoon on Friday and view ships as they make their way back to Chestertown following their afternoon sails. That evening, fireworks will light up the sky. 

A model boat and ship exhibit Saturday, October 30, will be held from 10 a.m. to 4 p.m. at the Project Shop at Sultana’s Holt Education Center. There you may see a variety of ship models and talk to their builders about the care and creation of the models.

On Saturday and Sunday, the waterfront will be brimming with speedboats from America’s golden age of wooden boats. Organized in partnership with the Antique and Classic Boat Society of the Chesapeake, this exhibit will feature some of the finest antique boats around.

Sailing and Bluegrass Music at Downrigging Weekend
In addition to the sailing vessels Downrigging Weekend has educational events, a music village, and much more. Photo by Michael Wooton

Are you a Bluegrass fan? The Music Village will host three days of bluegrass music, featuring a dozen artists. Ticket options include Friday and Saturday single-day admission or a combined Friday/Saturday ticket. Children under 12 are free. The Music Village is free and open to the public on Sunday.

Another highlight of the weekend is an exhibit by internationally renowned local artist Marc Casteli. His annual show at Massoni Art has become a Downrigging tradition. Expect to see unmatched renderings of watermen, workboats, and log canoes from a painter recognized as one of the finest marine artists in the country.

If you are coming with your wooden boat and are interested in reserving docking space and being part of the festival, please email Drew McMullen for more information. If you have a non-wooden boat, please contact the Chestertown Marina at (410) 778-3616 to inquire about slip space. There is plenty of room to anchor in the river and a dinghy dock is available at the marina.