The town's history is well-represented in Federal, Greek Revival and Victorian homes and other buildings. On German Street are Shepherd University, built in 1871, and the Entler Hotel, built in 1786.
The site of one of the earliest settlements in West Virginia, Shepherdstown was established by English and German farmers who had crossed the river from Pennsylvania into this area before 1730. The legal grant to the land was purchased by Thomas Shepherd in 1732. Originally named Mecklenburg, the name was changed to Shepherdstown in 1798. While living in Shepherdstown in 1787, James Rumsey gave the first public exhibition of his steamboat. A monument on the banks of the Potomac commemorates this successful demonstration.