Overview
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.
6 sights · 5 things to do · 1 places to eat · 1 places to stay
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Shepherdstown
Rumsey Monument
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 himse…
Morgan's Grove Park
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, …
Rumsey Steamboat Museum
This outbuilding houses a half-size working replica of the first Rumsey steamboat and information about James Rumsey's [2] life and invention.
Entler Hotel and Museum
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 parlor…
Little House and Little Barn
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 ceilin…
Elmwood Cemetery
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. A…
Plan your trip
Best time to visit & weather
Most comfortable: Apr–Oct. Summer highs reach about 90°F; winter lows dip to about 30°F. Very hot (Jul) — plan outdoor time for mornings. Wettest: Jul and Jun. (climate data from nearby Washington, D.C.)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- HGR Hagerstown Regional Richard A Henson Field, Hagerstown — 20 mi away. Directions
- IAD Washington Dulles International Airport, Dulles — 39 mi away (major hub). Directions
By car
Full “Get in” guide ↓Budget & where to stay
- Places to stay listed here: about $115–$115 a night (typical $152), from 2 listed prices.
- Estimated daily budget per person (room, two meals, local transport and an activity): budget ~$160, mid-range ~$230, comfortable ~$280.
See the Sleep guide ↓ for places to stay.
Sample 3-day itinerary
Day 1
- Morning Rumsey Monument, Little House and Little Barn
- Lunch Press Room
- Afternoon Contemporary American Theater Festival, Upper Potomac Music Weekends
Day 2
- Morning Morgan's Grove Park, Rumsey Steamboat Museum
- Afternoon Shepherdstown Music & Dance, Washington Heritage Trail
Day 3
- Morning Entler Hotel and Museum, Elmwood Cemetery
- Afternoon Shepherdstown Opera House
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Photos
Map
Every listing with a location. Tap a pin for its Google Maps link.
Get in
By car
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.
By plane
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.
Get around
There's limited public transportation in Shepherdstown. A bus Shuttle is provided for Shepherd University however, a car is most likely needed for the rest of the town. The town itself is compact and easily walkable, with most homes and the commercial area with a six block or so square.
See
See Rumsey Monument
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.
See Rumsey Steamboat Museum
This outbuilding houses a half-size working replica of the first Rumsey steamboat and information about James Rumsey's [2] life and invention.
See Entler Hotel and Museum
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.
See Little House and Little Barn
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."
See Morgan's Grove Park
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.
See Elmwood Cemetery
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.
Do
Do Contemporary American Theater Festival (CATF)
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.
Do Shepherdstown Music & Dance
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.
Do Shepherdstown Opera House
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.
Do 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.
Eat
Sleep
Stay Thomas Shepherd Inn B&B
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.
Go next
- 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.
Nearby
Sharpsburg
City / town · 11 listings · 4 mi away
Harpers Ferry
City / town · 24 listings · 8 mi away
Martinsburg
City / town · 26 listings · 9 mi away
Boonsboro
City / town · 6 listings · 10 mi away
Charles Town
City / town · 19 listings · 11 mi away
Brunswick
City / town · 10 listings · 13 mi away
Hedgesville
City / town · 1 listings · 13 mi away
Middletown
City / town · 3 listings · 14 mi away
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