Colonial settlers began their migration into the northern end of the Shenandoah Valley in the early 1700s. Many crossed the Potomac River at Pack Horse Ford, about one mile down river. 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 fifty acres and laid out a town. In 1762, the Virginia 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.

      In 1775, General George Washington issued a call for "Virginia Volunteer Riflemen." Captain Hugh Stephenson filled the ranks of his company here. The troops departed from "Morgan's Spring," about one-half mile south of the town limits, on July 16, 1775. This famous "Beeline March to Cambridge" covered 600 miles in twenty-four days. Thirty-eight Revolutionary veterans are buried in the surrounding area.

      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. The first Newspaper, The Potomac Guardian and Berkley Advertiser, and book, The Christian Panoply, in what is now West Virginia, were published here (1790s). The Shepherdstown Public Library has a copy of the book.

      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."

      Two free schools were built here in 1848. One still stands on the southeast corner of Princess and New Streets. When West Virginia became the 35th state (1863) these became the oldest free schoolhouses in the state.

      The Hamtramck Guard (The Shepherdstown Light Infantry) was dispatched to Harpers Ferry to subdue John Brown's raid on the Federal Arsenal (October 1859). At the outbreak of The War Between the States, this group became Company B, 2nd Virginia Infantry, Army of the Confederacy. They become part of the famous "Stonewall Brigade."

      After the Battle of Antietam, September 17, 1862, General Robert E. Lee's infantry crossed the Potomac at Pack Horse Ford. The town was overwhelmed with 5000-8000 casualties of that battle. Every house, building, church, alley and street was filled with the wounded and dying. The Battle of Shepherdstown (Boteler's Ford of Cement Mill) occurred on September 20, 1862. More than 100 Confederate soldiers died here and were buried in Elmwood Cemetery. Elmwood's hallowed ground contains the graves of 285 Confederate veterans, and offers its own self-guided walking tour. The graveyard is located five blocks south of the 4-way stop on Route 480.

      From 1865-1871, Shepherdstown served as the county seat of Jefferson County due to war damage to the courthouse in Charles Town. The Town Hall (northeast corner of German and King streets) housed the courthouse until it was moved back to Charles Town.

      In 1872, the Town Hall Building was chartered as a "Classical and Scientific Institute." The building was then leased to the state and Shepherd College was born. The East Campus occupies about one-third of the town proper and the West Campus occupies a large area just northwest of the corporate limits.

      Most of the town has been designated as a Historic District on the National Register of Historic Places. The rows of old houses are mostly intact, and the many fine homes and other buildings attest to the town's long history.

      Observe the number of brick buildings. Our clay soil was conducive to brick making. By the late 1790s, there were several commercial brickyards, and kilns could be built with little difficulty. In many instances, bricks were "burnt" at the construction sites. They were plentiful and cheaper than nails. Roofing material affected the market value and the insurance premiums of the brick structures. Those covered with tile were much more valuable then those topped with wooden shingles. Fires starting in the shingles destroyed many brick homes, mills, stores and outbuildings.