It was a Thursday in mid-June when Eric Vance and I brought our Chesapeake Light Craft Autumn Leaves solo cruisers to Cambridge, Maryland, at the mouth of the Choptank River. Our goal was simple: sail from the mouth of one of the bay’s many tributaries up to the farm town at the head of navigation. The weather here in the Chesapeake Bay area can be expected to take a turn to a calm, even sultry mood, and we expected to have leisurely sailing.Sailing to the towns well upstream on the Bay’s tributaries was once routine. Travel up any of the many rivers that empty into the Chesapeake as far as a cargo schooner can go, and you’ll find a town. And in each of these towns, there are stories of the days when the schooners would sail in frequently, bringing goods from Baltimore and picking up wood, grains, tobacco, and other farm products to be hauled back over these myriad watery roads to the city. But what would it be like to do a motorless cruise up one of these rivers today? Eric and I wanted to find out.

Roger Siebert

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