Regularly voted one of the “coolest small towns in America,” Shepherdstown boasts one-of-a-kind restaurants, art galleries, boutiques, coffee roasters, bookstores, markets, an outfitter, a bakery, and a general store.  The Shepherdstown Historic District boasts Federal-style brick homes along tree-lined streets.  Several lodging options are available, including guesthouses, B&B’s, and luxury hotels.      

In 1862, Shepherdstown became an unlikely Civil War field hospital, tending to nearly 8,000 wounded soldiers following the bloody Battle of Antietam in Sharpsburg, across the Potomac River. As Union forces chased Confederates south, the Battle of Shepherdstown became the deadliest action in what eventually became West Virginia.  The Historic Shepherdstown Museum contains exhibits detailing the town’s pivotal role during the war. Sharpsburg is a short on-road ride away, and features several bed and breakfasts as well as the Antietam National Battlefield, well-worth a day visit biking tour.

Nearby Landmarks

Shepherd University and its performing arts and public art installations makes for a lovely side trip. The Duke Street Underpass is adorned with a life-size abstract painting that draws from local elements – like rolling mountains, rhododendron, and chimney swifts. 

Fourteen preserved structures near Shepherdstown are on the National Register of Historic Places, including Shepherd’s Mill (1739), Boidstone’s Place (1766), and the Van Swearingen-Shepherd House (1773), and many are bikeable via local roads.  The 75-foot tall Rumsey Monument, commemorating mechanical engineer James Rumsey’s successful deployment of a steamboat in 1787, overlooks the Potomac River and makes a fine picnic spot.

Parking and Trail Access

Parking along the C&O Canal Towpath is in a dedicated lot adjacent to the towpath and across the Potomac River from Shepherdstown.  A winding bike and pedestrian path takes you up and over the river and into the Shepherdstown Historic District.