Downrigging Festival in Chestertown, Maryland

Downrigging Festival in Chestertown, Maryland

The annual event gives visitors a chance to explore the town's rich history--on sea and on land

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MOST CARS CROSS  the Chesapeake Bay Bridge and veer right toward the beaches, but on a late-fall day, I find myself steering left onto Route 213 to the historic port of Chestertown, Maryland. Founded in 1706 as a British royal port of entry and situated above a bend in the Chester River, this tidewater town—which bills itself as “America’s best preserved colonial seaport”—celebrates its heritage with some cool modern spins.

Visitors tour tall ships that linethe docks of Chestertown during Downrigging Weekend, held annually during the fall. Photo by Michael Ventura.

The occasion for my visit is the annual Downrigging Weekend, which started 15 years ago as a showcase of the many wooden vessels—tall ships, tiny cats, skipjacks, oyster boats—that have plied these waters for centuries. (This year’s event takes place Oct. 29 through Nov. 1; see The centerpiece of the festival is the Sultana, a locally built replica of a 1768 ship that the British used during colonial times to enforce tea tariffs.

I arrive early on a Friday afternoon amidst talk of a polar vortex that is bearing down on the region, though today the weather is mild and the Chester River is nearly flat, festooned with colorful flags that gently flap from atop the ships’ masts. Strolling the dock provides eye candy for any boating enthusiast.

From the impressive Sultana to its equally gorgeous counterpart, the Kalmar Nyckel (a replica of a colonial Swedish ship), each registered boat has a helpful placard indicating its name, origin and designer. I am drawn to the Shaker simplicity of the Aubrey, a small Beetle Cat built in 1967 that seems perfect for a romantic sail for two. (The Aubrey’s owner later gives a bagpipe concert on the dock.)

“How does the weather look?” I ask a festival worker who is manning the information tent. As advised, I’ve booked several cruises for the weekend (with fares ranging from $25 to $55 per person) in advance online. But the forecast is iffy.

“It would be good to get out on the water today,” she suggests. “The ships are doing private cruises, but you might talk your way on a boat.”

I'M NOT ONE to pull rank, but I long to be on the water below those billowing sails. Flashing the verbal equivalent of a press badge, I traipse from ship to ship, pleading for passage. Most turn me away, until the Pride of Baltimore II graciously allows me to stowaway, more or less, on an educational cruise sponsored by the sailing club of Washington College, which is also located in Chestertown.

Detailed wood carvings decorate the Kalmar Nyckel, a replica of a colonial Swedish ship. Photo by Michael Ventura.

The Pride is a replica of an 1812 topsail schooner—a Baltimore clipper—that ran circles around the more cumbersome British vessels, Capt. Jamie Trost explains. As we head out, the late-afternoon sun casts a honeyed glow on the other polished wooden ships passing by. Like Pride, most of the big ships in our midst serve as floating classrooms promoting history and environmental stewardship.

“Why are all those ropes everywhere?” a boy asks his dad, gesturing toward the neat coils that form the veins and sinews of the tall ship—the same ropes that will soon be tucked away for winter in the deconstruction known as downrigging (although the festival might be more aptly named pre-downrigging, given that visitors don’t get to see the ropes and sails actually being taken down).

“She runs on wind and muscle power,” Trost says to the boy, explaining the ship’s intricate system of masts, sails, pulleys and cables.

Wooden ships fill the Chester River during Downrigging Weekend every fall. Photo by Michael Ventura.

Next, he launches into a series of nautical yarns, starting with the origins of why it’s considered bad form to put one’s elbows on the dinner table. In colonial times, sailors usually ate with their elbows on either side of their plates to prevent the plates from sliding as the ship rolled, he explains, and British seafarers who were shorthanded would often scour harbor pubs and inns, looking for deserters and “volunteers.” Those who ate with their elbows on the table were presumed to have maritime training and were often pressed into His Majesty King George’s service.

Apocryphal or not (there is some disagreement online), it’s a great story.

Getting on the water gives me a prime view of the historic homes and gardens that line the shore of this quaint town, which, over centuries, gained prominence and wealth through tobacco, the slave trade and wheat. Nowadays its biggest business seems to be tourism.

Left: Jodi Bortz runs the antique letterpress at Book Plate. Right: Visitors can try the award-winning cream of crab soup at the Lemon Leaf Café. Photos by Michael Ventura.

No one seems to mind that the tall ships are accompanied by some potentially tall tales. Legend also has it that, five months after the Boston Tea Party revolt (news traveled slowly in 1744), residents of Chestertown, in an act of solidarity, dumped tea into the Chester River from the British ship the Geddes. Whether this event actually happened or not matters little to the locals who reenact the protest from the deck of the Sultana every Memorial Day weekend, when the town also offers cruises, tours, wine tastings and wandering minstrels (

TRUE TO FORECAST, the next morning brings lashing rains and winds gusting up to 40 mph, which keeps all the ships tied down. I entertain myself with the largest, most decadent cinnamon roll I’ve ever eaten at Simply Bed & Bread (, along with fresh fruit and a dollop of basil ice cream, before heading over to the town’s central square, with its ornate 1899 fountain of Hebe, cupbearer to the gods. On Saturdays, the square is filled with farmers and crafters hawking their wares. I buy a fun pair of fingerless alpaca gloves for my daughter.

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