Yorktown as a town was less than a century old. It had been a locally important, if still minor, port in the first half of the eighteenth century, but was in slow decline by the time the War for Independence began, and the war had effectively stopped its trade. It had been a major tobacco exporting centre, and there was a line of storage warehouses testifying to that. Along the shore there were wooden wharves with warehouses attached, and these installations were part of the reason Cornwallis had chosen it as the putative naval base. The town faced somewhat east of north, looking across the York River towards Gloucester Point and towards the wider opening which was the entrance to Chesapeake Bay. The York River was actually not so much a river as an inlet of the ocean, being unusually deep, and the water salty. It was said a ship could sail ‘upriver’ from Hampton Roads simply by weighing anchor when the tide came in.

The town, in European terms little more than a village, was the county seat, as well as a major trading port. It lay on two levels. Along the shore was the line of wharves and warehouses, and this was backed by a steep hill, not quite a cliff, from which a hollow way and the valley of the York Creek led inland and up to the plateau on which the rest of the town was built. This was at its highest close to the sea and sloped gently away inland to the south and south-west. The town was surrounded by forests and swampland, with the occasional plantation, but much of the soil had been exhausted by a century of monoculture exploitation.

The town had been carefully laid out with an eye to the geography. A single street, Main Street, ran parallel to the coast along the highest part of the land, a short distance inland from the edge; a series of streets led off this at right angles sloping off inland, and there were short extensions to these streets to the tip of the plateau, and so overlooking the beach. Two of these streets led on down to the shore and the warehouses, one along the hollow way and the other down the valley to the shore and the warehouses.