In 1787, Shepherdstown was the site of the first successful public launching of a steamboat. However, James Rumsey, inventor of the craft, died before he could exploit his success. Rival claims by John Fitch, and Robert Fulton's commercial success with the Clermont 20 years later, have clouded Rumsey's achievement.

The state's first newspaper was published here in 1790, and Shepherdstown almost became the national capital. (George Washington considered it as a possible site, according to letters in the Library of Congress.) Shepherdstown is also the location of one of the early gristmills, which is believed to have been constructed around 1739 and finally ceased production in 1939. This is the oldest continuously settled town in the state.