Shepherdstown is a small historic town in the Eastern Panhandle of West Virginia, on the Potomac River and near both the Maryland and Virginia borders. It is the oldest town in West Virginia, maintaining its historic structures and the charm of a small town but boasting of a vibrant downtown area with about a dozen restaurants, many small locally-owned shops, and an independent movie theater. The performing arts are a vital part of the town's culture, with the renowned Contemporary American Theater Festival at Shepherd University in the summer, live music at local venues throughout the year, and the historic Opera House movie theater showing independent and foreign films on weekends.
Shepherdstown is located at the intersection of WV Routes 230, 45, and 480. I-81 at Martinsburg, WV lies about 13 miles to the east, going by Route 45 and Route 9, and Harpers Ferry, WV, lies about 10 miles to the southwest, via Route 230 to Route 340. Route 70 is about 20 miles north and west via the town of Sharpsburg, MD (just three miles away) on MD Route 34 to MD Route 65, passing by Antietam Battlefield and continuing towards Hagerstown, MD. Washington, DC and its environs are about 70 miles away to the southwest.
The nearest commercial airports to Shepherdstown are Baltimore Washington International Airport in Baltimore and Dulles International Airport in Washington, D.C., both about 90 minutes away.
There's no public transportation in Shepherdstown, so you'll want to bring your car with you. The town itself is compact and easily walkable, with most homes and the commercial area with a six block or so square.
- Rumsey Monument, end of Mill St. until dusk. This town park commemorates James Rumsey, the inventor of the steamboat, and offers a panoramic view of the Blue Ridge Mountains, the Potomac River and the C&O Canal. Rumsey often walked these cliffs talking to himself about his inventions.
- Rumsey Steamboat Museum, corner of German & Princess (behind the Entler Hotel). This outbuilding houses a half-size working replica of the first Rumsey steamboat and information about James Rumsey's  life and invention.
- Entler Hotel and Museum, corner of German & Princess, ☏ . displays artifacts and preserves items of historic interest that might otherwise have been lost for people of Shepherdstown and Jefferson County. The first floor of the museum, formerly the ladies' and gentlemen's parlors, is now decorated as a formal reception room. The second and third floors include a room furnished as a hotel bedroom, a Victorian sitting room, and five rooms containing local artifacts including a fine display of local American Indian tools and artifacts. The museum is open seasonally on weekends; the reception rooms are available for shows and events. $4.
- Little House and Little Barn, Princess St. The smallest house in Shepherdstown. This supersized doll house was a Shepherd College project. Completed in 1929, the two-story "house" has five rooms and measures 10 feet high by 9-1/2 feet wide, with 5 1/2 foot ceilings. It was built so student teachers could observe children playing in the "Laboratory setting."
- Morgan's Grove Park, Route 480 (corner of Route 480 and bypass), ☏ . With over 20 acres of shade trees, meadows, playgrounds and spring-fed streams, Morgan's Grove Park serves as an idyllic site for community gatherings, such as the annual Labor Day Community Picnic. Morgan's Grove Park, formerly known as Morgan's Grove Fair was once the site of fairs, horse races, camp meetings, patriotic celebrations and other community events. In 1999, it was entered in the National Register of Historic Places. Morgan's Grove Park is available for rental. For information on availability or rental rates, please call Jefferson County Parks and Recreation at the number above.
- Elmwood Cemetery, Duke St. There are approximately 120 graves of casualties of the Battle of Antietam buried in the "Soldiers Graveyard" near the front of Elmwood. There are an additional 120 Confederate veterans' graves throughout the cemetery. An "Army of Northern Virginia" battle flag marks each.
- Contemporary American Theater Festival (CATF), PO Box 429, toll-free: . Dedicated to producing and developing new American theater, the Contemporary American Theater Festival is one of America's most vital new play development centers. The Festival presents new American plays in rotating repertory each summer on the campus of Shepherd University in Shepherdstown.
- Shepherdstown Music & Dance, PO Box 1293, ☏ . Folk music society dedicated to the preservation and perpetuation of traditional music and dance. We sponsor 1st and 5th Saturday contra dances at the War Memorial Building, concerts (usually on the Shepherd University Campus), morris dancing and the Shepherdstown May Day Celebration.
- Shepherdstown Opera House, 131 W. German St, ☏ . The Shepherdstown Opera House, one of the nation's oldest movie theatres, first begin showing films in 1909 until 1958, when it was closed and abandoned. Today, the Opera House uses the finest projection and sound systems available to entertain a new generation with the best movies being made today.
- Upper Potomac Music Weekends, PO Box 1474, ☏ . Music workshops for traditional folk musicians including two Dulcimer Fests (March and September), an Irish Music Weekend and a Fiddle Retreat. Public Concerts and evening programs are usually featured as part of each event.
- Washington Heritage Trail. Follow the footsteps of America's first president and Founding Father when you travel the Washington Heritage Trail in West Virginia. So much of George Washington's history is preserved and relived along the Byway that you can almost feel his presence. Travel through farms and apple orchards and enjoy the scenic beauty of the area as you explore the history of the people and places that shaped this great nation. The Washington Heritage Trail is a loop route, so you can begin and end your tour anywhere along the way.
- Press Room, German St, ☏ .
- Thomas Shepherd Inn B&B, corner of German & Duke Streets, ☏ . Check-in: 3PM, check-out: 11AM. Located in the heart of historic Shepherdstown, this restored 1868 federal style property offers elegant decor, beautiful antiques and a relaxing atmosphere. Six air conditioned rooms (each with private bath) are furnished appropriately for the period. Each morning begins with a full homemade breakfast. $115-$190.
More information about Shepherdstown can be found on the Shepherdstown Visitors Center website, .
- Martinsburg is about 10 miles east on route 45.
- Harpers Ferry is about 10 miles southwest on route 230.
- Charles Town is about 10 miles southeast via route 9.
- Hagerstown, Maryland is about 30 minutes northwest.
- Winchester, Virginia is about 45 minutes southeast via Route 81.