The Secrets of the Chester

The gales of November came early this year and stymied my attempts to reach Chestertown for Downrigging Weekend, a festival begun as a quiet reflective end to the schooner Sultana’s sailing season as she is decommissioned for winter hibernation.

Tucked into a cove on Queenstown Creek, I weighed anchor November 1 amid driving rain and increasing winds in search of a marina to wait out the Nor’easter that was organizing itself off the Carolina coast. After tying up, plugging in, and cranking up the heat in Langford Creek, I had a lot of free time to contemplate my surroundings. Of all the rivers on the Eastern Shore, the Chester is a standout favorite. It’s neither the longest nor perhaps the most serene, but it is long enough, wide and deep, and in a few places, complicated. After the temporary looking vinyl sided condos of Kent Island and Grasonville are put well and truly astern, you keep waiting for the next round of 21st century tackiness to hove into view and spoil it.

But it never does.

Not, at least, until Kingstown, 26 miles upriver does the specter of unimaginative planning play out with ugly sprawl on the Queen Anne’s County side. Until then, for mile after bucolic mile, there is little to suggest that you might not be back in the late 18th century.

In fact, that’s about the time that the Chester, and its officially designated port of entry, Chestertown, began its slow decline as a victim of geography and accidentally turned into one of the best preserved and authentic colonial settlements in America. All of this is thanks to, somewhat chronologically, the emergence of Baltimore as a major seaport, the invention of the steamship, westward expansion of the nation, the development of railroads that opened up trade to the hinterlands, a road network that bypassed the town, and finally, land preservation efforts in recent times that have kept agriculture strong and housing development to a minimum.

The Census of 1790 found Chestertown to be the center of population of all the United States. Photo courtesy of the Maryland Department of Planning

But the fact that Chestertown did exist as a port of some significance warrants some examination. Twenty-six miles is a long slog upriver from the Bay for a sailing vessel. Obviously this was worth the trip for wind driven vessels of commerce, but modern day sailors seem to avoid it.

“You’ll have to motor the whole way,” they’ll tell you. What fun is that? But looking at wind velocity and frequency maps shows a concentration of wind in the Chester, and since in the upper reaches the river twists and turns like a discarded feather boa, there’s bound to be wind on most points of sail. And there is.

The other thing the Chester has in its favor is a relatively benign current. Tidal ranges aren’t great, and colonial ship captains didn’t find much trouble with it. If they had, it’s unlikely that Chestertown would have developed so spectacularly. Here you will find a great variety of high style colonial architecture, comparable to and in some ways exceeding that found in Annapolis. Chestertown was the Philadelphia of its day. It was, in fact, right along the favored land and sea route between Washington and Penn’s city to the north.

The Census of 1790 found Chestertown to be the center of population of all the United States until the country shifted west and left Chestertown to slumber for a couple of centuries. If the secret of the Chester River is wind, and lots of it, why isn’t God and everybody over there crowding her waters like any other popular place on the Chesapeake? Perhaps it holds little of interest to the modern cruiser. Marinas are few, gas and diesel are hard to find, and I can’t think of a single waterside restaurant or tiki bar. Sounds perfect to me.

Enter the Sultana. A replica 1768 British revenue schooner, the Sultana is the star of the Chestertown Tea Party, established long before the term was borrowed for modern political purposes. Home ported in Chestertown since being built and launched there in 2001, Sultana has reawakened the town’s importance as a seaport and since the inception of Downrigging Weekend, has hosted one of the most fascinating wooden boat shows that few have ever heard of. Or can get to. Sail up the river looking to score a slip for the night during Downrigging will bring disappointment and a cold night on the hook. Every slip in the municipal marina is given over to Downrigging.

Tying up along the seawall isn’t an option, and the anchorage needs to be clear in order for the big boys to maneuver. The Sultana is one of Chestertown’s greatest assets, bookending each year with the Tea Party in May and culminating with Downrigging just after Halloween. It’s that Chestertown isloation again. A dearth of hotel rooms and even fewer marina slips all add up to a great festival that nobody can get to. But the people still come. And that suits Chestertown just fine.

by Steve Allan