As of the census of 2000, there were 803 people, 410 households, and 168 families residing in the town. The median income for a household in the town was $40,750, and the median income for a family was $55,000.
Colonial settlers began their migration into the northern end of the Shenandoah Valley in the early 1700s. The Colony of Virginia began issuing Valley land grants in the 1730s. In 1734, Thomas Shepherd was granted 222 acres on the south side of the "Potowmack" river, along the Falling Spring Branch (now known as the Town Run). From that tract he selected 50 acres and laid out a town. In 1762, the Virginia General Assembly chartered the town of Mecklenburg. Thomas Shepherd was the sole trustee: he owned the town and was responsible for its government. More than twenty natural springs feed Town Run before it enters the south end of town. It never floods, nor runs dry; it meanders through backyards, under houses, across alleys and beneath five streets. This setting was conducive to millers, tanners, potters, smiths and other artisans. As a result, by 1775 it boasted 1,000 inhabitants.
On December 3, 1787, James Rumsey conducted a successful trial of his new invention, the steamboat, in the Potomac at the north end of Princess Street. A second charter, which allowed for self-government, was granted in 1794. In 1798, the corporate limits were extended and the name was changed to Shepherd's Town. After the Civil War, the town's name was officially contracted to Shepherdstown. The part of the C&O Canal, across the river from Shepherdstown, was built during the 1830s. Shepherdstown is the only town, in what is now the state of West Virginia, to have a canal lock named for it. Lock No.38 was the "Shepherdstown Lock."
After the Civil War Battle of Antietam, September 17, 1862, General Robert E. Lee's infantry crossed the Potomac at Pack Horse Ford. The town was overwhelmed with 5000 to 8000 casualties of that battle. Every house, building, church, alley and street was filled with the wounded and dying. The Battle of Shepherdstown (also known as the Battle of Boteler's Ford or Cement Mill) occurred on September 20, 1862, during Lee's retreat. More than 100 Confederate soldiers died here and were buried in Elmwood Cemetery.
Presently, many of the town's historical buildings on German Street are home to quaint little shops and cafés. The town is also home to many local artistic and theatrical groups, many of which are affiliated with Shepherd University or operated by youth groups.
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