Boteler's Ford was a mile and a half downstream from the town of Shepherdstown, Virginia (now West Virginia) and also called Blackford's Ford and Pack Horse Ford and had been a spot to cross the Potomac River since colonial times. When the water was down, the stony shelf of the ford was clearly visible. However, during the Confederate retreat it was described as "deep and rocky" by Confederate artillery officer Lt. Col. Edward Porter Alexander.
The Chesapeake & Ohio Canal followed the Potomac River on the Maryland side through here. The war had been hard on the canal and its berm had been destroyed in numerous places, draining the channel. Rolling hills on the Maryland side offered Union artillery abundant sites. There were heights on the Virginia side, but they were somewhat steep and made for difficulty in placing artillery for the Confederates.
Roads on both sides leading to the ford were so narrow in places that it was difficult for a horse to pass a wagon.
Lee expected McClellan to, at some point, pursue him and was aware that the ford should be defended until his army was well away from it. Perhaps because so many able officers had been lost on September 17, he chose William Pendleton, an officer with little combat experience, to guard Boteler's Ford.
--Old Secesh
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