Chartered in 1762, Shepherdstown is the oldest town in West Virginia and 30 years older than the United States. With many of its buildings pre-dating the Revolutionary War, you will find history and charm around every corner. Situated along the banks of the Potomac River, and just 70 miles north of Washington, DC, and west of Baltimore, MD, Shepherdstown is a mixture of metropolitan thought and rustic ambience.
During its over 200 years, Shepherdstown has played a pivotal role at important periods of American history. It was in Morgan’s Grove Park, just 3 miles from Rock Spring Retreat, that in July 1775 just over 100 backcountry militiamen set out on the 600 mile Bee Line march to Cambridge, Massachusetts in response to General George Washington’s request for men to compose the Continental Army at the beginning of the Revolutionary War. It is for this reason that Morgan’s Grove Park is known as the birthplace of the United States Army. You can find more information about Shepherdstown sites associated with the colonial and Revolutionary War period here.
Shepherdstown again sat at the crossroads of history during the American Civil War where it was pivotal in Lee’s Maryland campaign of 1862 and many of the 1,500 days of armed conflict in our country. During the battles of South Mountain, Antietam, and Shepherdstown, the town switched hands between the Union and Confederacy on multiple occasions. It was during this time that nearly every building in town served as a massive makeshift field hospital for 8,000 wounded Confederate soldiers. The plaque in front of Trinity Episcopal Church on German Street tells the story of how the church’s congregation shifted back and forth from Union soldiers to Confederate soldiers again and again over the course of the war. Rock Spring Retreat has its own story in this chapter of American history, when in November 1864 Henry Miller Snyder, a Confederate soldier home on leave, was killed in the foyer of the house where you are staying by intruders who were trying to rob his elderly parents. To learn more about the fascinating history of Shepherdstown, plan a visit to the Historic Shepherdstown Museum on German Street.
Shepherdstown is also home to Shepherd University, a public liberal arts college established in 1871 and home to a student population of 3,100. Each July, Shepherd University is host to the Contemporary American Theatre Festival, an annual festival of new plays by American playwrights. Each summer Shepherdstown swells with the actors, directors, choreographers, technicians, and coordinators from around the world who bring the festival to life. In its 2019 season, the festival Issued over 18,500 tickets to 6,000 patrons from 38 states, DC, and around the globe.
With its mix of history and culture, it's no wonder that Budget Travel lists Shepherdstown as one of the Coolest Small Towns in America.