Did you know Shepherdstown is West Virginia’s oldest town, founded in 1762? As you wander its charming streets, you’ll be walking the same paths once frequented by Revolutionary War heroes and Civil War soldiers. This historic gem along the Potomac River offers a perfect blend of small-town charm, outdoor adventure, and cultural experiences that make it an ideal getaway destination just 130 km (80 miles) from Washington, D.C.
Getting There & Planning Your Journey
Shepherdstown is conveniently located in West Virginia’s Eastern Panhandle, making it easily accessible from several major cities. The nearest major airports are Dulles International Airport (IAD) and Ronald Reagan Washington National Airport (DCA), both approximately 100 km (62 miles) away.
By Car
Most visitors arrive by car via these routes:
- From Washington D.C.: Take Route 270 to Route 340 West (approximately 1.5 hours)
- From Baltimore: Take I-70 West to Route 340 South (approximately 2 hours)
- From Pittsburgh: Take I-76 East to I-70 East to Route 340 South (approximately 4 hours)
By Public Transportation
While limited, there are public transportation options:
- MARC Train to Harpers Ferry, then taxi to Shepherdstown (10 miles)
- Amtrak to Martinsburg, then taxi to Shepherdstown (15 miles)
Ready to Plan Your Trip?
Find the best flight deals to Washington D.C. and rent a car to explore Shepherdstown and the surrounding area at your own pace.
Best Time to Visit & Weather Tips
Recommended Seasons
- Fall (September-October): The ideal time to visit with temperatures between 15-20°C (59-68°F) and stunning foliage along the Potomac River and C&O Canal Towpath.
- Spring (April-May): Pleasant weather with temperatures around 18-24°C (65-75°F) and beautiful blooming flowers throughout town.
- Summer (June-August): Warm at 25-32°C (77-90°F) with occasional humidity, but perfect for water activities on the Potomac.
Seasons to Avoid
- Winter (December-February): Cold temperatures averaging 1°C (34°F) with occasional snow can limit outdoor activities. However, this can be a charming time to visit if you enjoy quiet, cozy getaways.
Shepherdstown hosts several festivals throughout the year, including the Contemporary American Theater Festival in July and BooFest in October, which may affect accommodation availability.
Getting Around Locally
Shepherdstown’s compact size makes it perfect for exploring on foot. The historic downtown area spans just a few blocks, with most attractions, restaurants, and shops within easy walking distance of each other.
Walking
The most enjoyable way to experience Shepherdstown is on foot. The historic district is highly walkable, with charming streets and hidden gems around every corner. Pick up a self-guided walking tour map at the Shepherdstown Visitors Center on German Street.
Biking
Rent bikes from Shepherdstown Pedal & Paddle on German Street to explore the town and venture onto the C&O Canal Towpath. This is an excellent option for reaching attractions like the Rumsey Monument or exploring the scenic paths along the Potomac River.
Where to Stay
Shepherdstown offers a variety of accommodation options, from historic bed and breakfasts to modern hotels. Most lodging is either in the historic downtown area or within a short drive.
Historic B&Bs
Experience the town’s history by staying in one of the charming bed and breakfasts housed in historic buildings. The Thomas Shepherd Inn and Shepherdstown Inn offer period furnishings and homemade breakfasts.
Bavarian Inn Resort
This European-inspired boutique resort sits on 11 acres overlooking the Potomac River. It features German cuisine, an on-site brewery, and an infinity pool with river views. It’s within walking distance of downtown.
Budget Options
Several chain hotels and motels are available in nearby Charles Town and Martinsburg, offering more affordable options just a short drive from Shepherdstown.
Find Your Perfect Shepherdstown Accommodation
Book early, especially during festival seasons and fall foliage weekends when accommodations fill quickly.
Dining & Local Cuisine
Shepherdstown’s dining scene is surprisingly diverse for a small town, offering everything from casual cafes to fine dining experiences. Many restaurants emphasize farm-to-table ingredients sourced from the surrounding Shenandoah Valley.
Blue Moon Cafe
Housed in a former gas station, this local favorite offers a casual menu with something for everyone. The outdoor dining space next to the Town Run creates a secret garden atmosphere. Try their crab melts or Gobbler sandwich with smoked turkey.
The Press Room
Located in a historic newspaper building, this upscale restaurant requires reservations. Their menu features sophisticated dishes like grilled sea scallops with mushroom risotto and smoked salmon pasta. Don’t miss their lavender crème brûlée for dessert.
Bavarian Inn Restaurant
Experience authentic German cuisine at The Potomac Room, featuring dishes like Schweineschulter (slow-roasted pork shoulder) and traditional apple strudel. For a more casual experience, visit their Rathskeller or the Bavarian Brothers Brewing Company.
Local Specialties to Try
- Pepperoni Rolls: A West Virginia specialty that originated as a portable lunch for coal miners
- Apple Strudel: Reflecting the area’s German heritage
- Chesapeake Crab Dishes: Showcasing the region’s proximity to the Chesapeake Bay
- Craft Beer: From Bavarian Brothers Brewing and other local breweries
Attractions & Sightseeing
Historic Downtown & German Street
The heart of Shepherdstown is its well-preserved historic district centered around German Street. Buildings dating back to the 18th century now house boutique shops, restaurants, and galleries. Don’t miss these highlights:
- O’Hurley’s General Store: A 120-year-old building offering an eclectic mix of goods from cookware to candles. The owner was born upstairs and built the attached Great Hall.
- Shepherdstown Public Library: Located in the former Market House building (built in 1800), it’s West Virginia’s longest continuously occupied library.
- “The Little House”: A fully furnished, 10-foot-tall Dutch Colonial-style child-sized house built between 1928 and 1930.
- Shepherdstown Sweet Shop Bakery: Housed in a 200-year-old building, specializing in Old World-style artisan bread and pastries.
- Mountaineer Popcorn Company: Offering unique flavors of locally grown popcorn, including “Loaded Baked Potato” and “Breakfast Munch.”
- Hive House Apiaries: A beekeeper supply store where you can purchase local honey and learn about beekeeping.
James Rumsey Monument & Steamboat History
Visit the 75-foot granite monument dedicated to James Rumsey, who successfully demonstrated the first steamboat on the Potomac River at Shepherdstown in 1787. The monument offers excellent views of the Potomac River and surrounding area.
Explore Shepherdstown’s Hidden Gems
Discover the best of Shepherdstown with guided tours that reveal the town’s fascinating history and secret spots.
Outdoor Activities & Nature
Potomac River Recreation
The scenic Potomac River forms the border between West Virginia and Maryland, offering numerous recreational opportunities:
- Kayaking & Canoeing: Rent equipment from Shepherdstown Pedal & Paddle for guided or self-guided trips on the river.
- Fishing: The river is known for smallmouth bass fishing, with several access points near town.
- Swimming: During summer months, locals enjoy cooling off at several swimming spots along the river.
C&O Canal Towpath
The historic Chesapeake & Ohio Canal Towpath runs for 185.4 miles from Washington, D.C. to Cumberland, Maryland. The section near Shepherdstown is particularly scenic and perfect for:
- Biking: The flat, shaded trail is ideal for cyclists of all skill levels. Rent bikes in town and cross the river to access the towpath.
- Hiking: Enjoy peaceful walks along the canal with views of the Potomac River and abundant wildlife.
- Bird Watching: The area is home to bald eagles, herons, and numerous other bird species.
- Photography: Capture stunning river views, historic canal structures, and seasonal foliage.
Museums, Cultural Spots & Festivals
Museums & Historic Sites
Shepherdstown’s rich history is preserved in several museums and historic sites:
- Historic Shepherdstown Museum: Located in the Entler Hotel, the museum displays artifacts dating back to the town’s founding and Civil War period.
- Rumsey Steamboat Museum: Learn about James Rumsey’s pioneering work on steam-powered boats and see a working replica of his original steamboat.
- Shepherdstown Visitors Center: Pick up self-guided walking tour maps and learn about the town’s history from knowledgeable staff.
Cultural Events & Festivals
Despite its small size, Shepherdstown hosts several significant cultural events throughout the year:
- Contemporary American Theater Festival (July): One of the top theater festivals in the US, featuring new plays by American playwrights at Shepherd University.
- BooFest (October): A Halloween celebration with parades, ghost tours, and family activities.
- Christmas in Shepherdstown (December): Holiday events including tree lighting, parades, and seasonal markets.
- Street Fest (June): A celebration of local arts, crafts, and music.
Experience Shepherdstown’s Cultural Scene
Check event schedules and book tickets in advance, especially for the popular Contemporary American Theater Festival.
Day Trips From Shepherdstown
Shepherdstown’s location makes it an ideal base for exploring other attractions in the region:
Harpers Ferry
Just 10 miles away, this historic town sits at the confluence of the Potomac and Shenandoah Rivers. Visit Harpers Ferry National Historical Park to learn about John Brown’s raid, enjoy hiking trails, and explore the picturesque lower town.
Antietam National Battlefield
Located 10 miles northeast in Sharpsburg, Maryland, this preserved Civil War battlefield was the site of the bloodiest single-day battle in American history. The visitor center offers exhibits and self-guided tour maps.
Charles Town
Visit this nearby town for its Hollywood Casino, historic sites related to George Washington’s family, and additional dining options.
Practical Travel Tips
Local Transportation
There is no public transportation within Shepherdstown itself, but taxis are available for trips to nearby towns. Having a car is recommended for exploring the region beyond the town center.
Parking
Metered parking is available on German Street and surrounding areas. Most meters accept coins only, so keep some quarters handy. Free parking can be found at the Shepherd University parking lots on weekends and after 4 PM on weekdays.
Local Shopping
The Shepherdstown Farmers Market operates on Sundays from April through December, offering local produce, baked goods, and crafts. It’s a great place to pick up picnic supplies or souvenirs.
Wi-Fi Access
Free Wi-Fi is available at the Shepherdstown Public Library and most cafes in town, including Lost Dog Coffee and Four Seasons Books.
Is Shepherdstown suitable for families with children?
Yes, Shepherdstown offers family-friendly activities including Morgan’s Grove Park with playgrounds, kid-friendly hiking on the C&O Canal Towpath, and The Little House, which fascinates children. Many restaurants also offer children’s menus.
Are there any ghost tours in “America’s Most Haunted Town”?
Yes, Shepherdstown Ghost Tours operate regularly, especially during the fall season. These walking tours explore the town’s haunted history, including buildings that served as Civil War hospitals. Reservations are recommended.
Ready to Experience Shepherdstown?
From its cobblestone streets lined with historic buildings to the scenic beauty of the Potomac River, Shepherdstown offers a perfect blend of history, culture, and outdoor adventure. Whether you’re a history buff, outdoor enthusiast, foodie, or simply looking for a charming getaway, West Virginia’s oldest town delivers an experience that feels both timeless and fresh.
Start planning your Shepherdstown adventure today and discover why this small town continues to captivate visitors more than 250 years after its founding. The historic buildings, friendly locals, and beautiful natural surroundings are waiting to welcome you to one of West Virginia’s most treasured destinations.
Plan Your Shepherdstown Getaway
Book your accommodations, transportation, and activities now to ensure the best experience in this charming historic town.
The above is subject to change.
Check back often to TRAVEL.COM for the latest travel tips and deals.
