About Shepherdstown, West Virginia
West Virginia’s oldest continuously chartered town, Shepherdstown sits on a limestone bluff above the Potomac River. A walkable, restaurant-lined main drag, German Street is one of the finest small-town commercial corridors in the Mid-Atlantic.
The C&O Canal towpath runs along the Potomac below the bluff, accessible to downtown via a ramp at Canal Mile 72.7 and across the Potomac on Shepherdstown Pike (WV-34). Shepherdstown Pedal & Paddle, right on German Street, offers bike and kayak rentals and shuttle service, making this one of the few canal towns where visitors can arrive on the trail, pick up a kayak, paddle the river, and then walk to dinner without a car.
The Bavarian Inn, perched on a hillside overlooking the Potomac, serves as Shepherdstown’s anchor resort — a AAA Four Diamond property with formal dining, a craft brewery, and an infinity pool. But the town’s real texture lives on German Street: Shepherdstown has more good restaurants than towns twenty times its size, while Shepherd University adds intellectual energy and keeps the town’s arts calendar full.
Getting There
Parking Access
The C&O Canal runs along the Maryland side of the Potomac, about one mile from Shepherdstown’s town center. From the corner of German Street and Princess Street, head east on Shepherdstown Pike (WV-34) toward the river and cross the bridge into Maryland. Turn right on Canal Road and follow it to Lock 38 Parking Lot.
River Access
The Princess Street Boat Ramp in Shepherdstown provides concrete single-lane access to the Potomac, with parking for eight vehicles. The site sits just downstream from the New Rumsey Bridge, near the historic spot where inventor James Rumsey famously demonstrated one of America’s first steamboats in 1787.
Where to Stay
The Bavarian Inn is the standout lodging option in Shepherdstown — a AAA Four Diamond resort perched on a bluff overlooking the Potomac River with 72 rooms, many featuring gas fireplaces, whirlpool baths, and river views. The property also includes a brewery, infinity pool, and award-winning dining. For a quieter stay, the Thomas Shepherd Inn is a well-regarded B&B in the heart of the historic district. Hiker/biker campsites are available on the Maryland towpath just across the river.
Town Highlights You Don't Want to Miss:
Where to Eat & Drink:
Among many dining options, a few stand out: the Blue Moon Café draws locals and visitors alike with its eclectic menu; The Press Room offers well-executed pasta, seafood, and meat dishes; and the Bavarian Inn pairs stunning river views with food to match. For something sweet and snackable, Rock Hill Creamery and Mountaineer Popcorn are both worth a stop.
For History Lovers:
Just across the Potomac on the Maryland bluffs, Ferry Hill Plantation offers sweeping views back toward Shepherdstown and a fascinating window into Civil War history. The 1812 estate served as a Confederate headquarters and hospital during the Antietam campaign and is now part of the C&O Canal National Historical Park. Back in Shepherdstown, the Historic Shepherdstown Museum in the 1786 Entler Hotel interprets 300 years of life in West Virginia’s oldest town, with rotating exhibits and walking tour maps for the remarkably intact historic district. Elmwood Cemetery, where 285 Confederate veterans are buried, offers its own self-guided walking tour.
For Outdoor Enthusiasts:
The Potomac River at Shepherdstown offers flatwater paddling, tubing, and fishing from the Princess Street boat ramp, with the C&O Canal towpath at mile 72.7 providing easy access for cyclists and hikers. The town sits at a natural crossing point used since the 18th century, and the views from the riverbank are among the best on this stretch.
For Arts Lovers:
Shepherdstown has a creative scene that surprises most visitors. Each July, the Contemporary American Theater Festival transforms Shepherd University into one of the country’s most respected new-play festivals, premiering original American works and drawing talent from New York and beyond. Tickets sell out, so plan ahead if you’re visiting in summer. German Street boasts galleries, studios, and artisan shops carrying original work in painting, photography, ceramics, and craft.
Photos by Rebekka Hudson