Shepherdstown, WV

Travel Guide

A street lined with brick buildings, including a bank and a restaurant.
A historic street with red brick buildings, a church steeple, and a sign for a local shop.
A street with a red brick building, a sign for Maria's Taco, and a sign for Grapes & Grains Gourmet.
A row of bicycles parked against a metal bike rack on a city street.
A vintage storefront with a sign reading "Open Soon... Pop on in!" and a vintage suitcase.

Explore funky bars and coffee houses and experience the diverse cultural scene at this exciting and dynamic college town.

Shepherdstown is a small town, yet it possesses a vivacity and energy more typical of a larger city. It was officially incorporated in 1762 under the name Mecklenburg and has plenty of historical pre-Revolutionary architecture. The town has more to offer visitors than just its historical features. Shop for handicrafts in local shops, attend arts-oriented festivals and hike the trails at nearby state parks.

Before you delve into the student-driven arts scene, familiarize yourself with the town’s more than 250 years of history. Wander around the Shepherdstown National Historic Districtand identify the different architectural styles. Find Grand Greek-Revival buildings as well as Federal and Victorian constructions around town. Pick up a map of historic homes at the Shepherdstown Visitors Center to help you navigate. The Historic Shepherdstown Museum, housed in an 18th-century hotel, is open from early April to late October and is devoted to local history.

The presence of students in the small town adds to its youthful atmosphere. Mingle with students at the Shepherd University campus near the banks of the Potomac River. Spend evenings in the busy bars where students congregate for nights out. Consider booking tickets for a show at the historic Shepherdstown Opera House, which screens films and eclectic live events.

Find cafés, restaurants and interesting shops selling antiques as well as handcrafted goods on the main thoroughfare, German Street. Walk or bike in the Chesapeake and Ohio Canal National Historical Park, running along the northern bank of the Potomac River and stretching all the way to Washington D.C.

The town has a busy events schedule, with several well-known festivals throughout the year. Arrange your trip to coincide with the renowned summertime Contemporary American Theater Festival. Film buffs may want to catch the Cut to the Chase Film Festival in September or the American Conservation Film Festival later in the fall.

Shepherdstown is about a 90-minute drive from Washington D.C. and Baltimore. Discover the arts and festival scene that has Washington weekenders enamored.

Quality Inn Shepherdstown

Quality Inn Shepherdstown

2.5 out of 5
70 Maddex Square Dr Shepherdstown WV
$83 nightly
The price is $93 total per night from Nov 1 to Nov 2
$93 total
Nov 1 - Nov 2
Total with taxes and fees
Stay at this hotel in Shepherdstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maddex Square and Bane Harris Community Park are ...
Quality Inn Shepherdstown
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown WV
$101 nightly
The price is $112 total per night from Oct 25 to Oct 26
$112 total
Oct 25 - Oct 26
Total with taxes and fees
Stay at this cabin in Shepherdstown. Enjoy free WiFi, a garden, and patios. Popular attractions Rumsey Monument and Scarborough Library are located nearby.
9.6/10 Exceptional! (86 reviews)
"Room was clean and provided with all the essentials. Plenty of extra towels and blankets as well. Grill was in good working condition and clean. Plenty of propane was provided. Outside shower / sink were clean and in good working order. Pit toilet was in clean and in good shape. Really enjoyed the ..."

Reviewed on Sep 30, 2026

❤️ Secluded 1940s Romantic Tiny House on the River
Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

3 out of 5
17612 Valley Mall Rd Hagerstown MD
$83 nightly
The price is $93 total per night from Nov 8 to Nov 9
$93 total
Nov 8 - Nov 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Hagerstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Country Inn & Suites by Radisson, Hagerstown, MD
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown WV
Stay at this cabin in Shepherdstown. Enjoy free WiFi, a garden, and patios. Popular attractions Rumsey Monument and Scarborough Library are located nearby.
9.6/10 Exceptional! (86 reviews)
"Room was clean and provided with all the essentials. Plenty of extra towels and blankets as well. Grill was in good working condition and clean. Plenty of propane was provided. Outside shower / sink were clean and in good working order. Pit toilet was in clean and in good shape. Really enjoyed the ..."

Reviewed on Sep 30, 2026

❤️ Secluded 1940s Romantic Tiny House on the River
Mirror Villas - Modern Retreat with private hot tubs and mountain view

Mirror Villas - Modern Retreat with private hot tubs and mountain view

3.5 out of 5
13571 Blairs Valley Rd Mercersburg PA
Stay at this chalet in Mercersburg. Enjoy free WiFi, free parking, and private hot tubs. Popular attractions Lift Off Quad Ski Lift and Magic Carpet Ski Lift ...
10/10 Exceptional! (26 reviews)
"This space provided such a beautiful, serene experience. Could not have asked for anything more. They had everything we needed from fire starter to bottled water. There are so many delicate touches that made the space that much more comfortable. The bed was incredibly cozy, the heated floors were ..."

Reviewed on Sep 20, 2026

Mirror Villas - Modern Retreat with private hot tubs and mountain view
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Frederick MD
Stay at this vacation home in Frederick. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions National Museum of Civil War Medicine ...
9.2/10 Wonderful! (141 reviews)
"I has very happy with the cleanliness and location of the property. Definitely love having parking directly behind the home. No doubt I will stay here again when coming back to Frederick Maryland...."

Reviewed on Sep 22, 2026

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Shepherdstown attractions

Things to do

Frequently asked questions

Is Shepherdstown worth visiting?
Shepherdstown is worth visiting for its unique attractions and diverse dining. Travelers can explore Shepherd University and enjoy performances at the Shepherdstown Opera House. The town also offers a variety of food options, including Italian and Asian cuisine, providing a range of choices for meals.
When is the best time to visit Shepherdstown?
The best time to visit Shepherdstown is from June through August, when the destination is most popular. For travelers seeking fewer crowds and better value, the quieter months of November through January are a good option, offering a more relaxed experience.
What is Shepherdstown known for?
Shepherdstown is known for Shepherd University, a central educational institution. Travelers can also visit the historic Shepherdstown Opera House for cultural events and explore local heritage at the Shepherdstown Museum.
What is a good itinerary length for Shepherdstown?
A good itinerary length for Shepherdstown is one to two days to explore highlights like Shepherd University, the Shepherdstown Opera House, and the Shepherdstown Museum. An extended stay of three to four days allows travelers to take the Shepherdstown Haunted Self Guided Audio Walking Tour and enjoy the local dining, including Italian, Asian, and European cuisine.
What are the top things to do in and around Shepherdstown?
Shepherdstown offers a blend of historical exploration, cultural sites, and unique local experiences:


How do I plan a trip to Shepherdstown?
To plan your trip to Shepherdstown, search for places to stay on Expedia and book flights and rental cars in advance. Explore attractions like Shepherd University, the Shepherdstown Opera House, or take the Shepherdstown Haunted Self Guided Audio Walking Tour. For outdoor activities, always have indoor backups ready for weather flexibility.
What cuisines can you find in Shepherdstown?
In Shepherdstown, travelers can find Greek cuisine, with dishes like moussaka, souvlaki, gyros, and spanakopita. Travelers can also enjoy a variety of other options, including Italian, Asian, North American, and Latin American dishes, offering a diverse range of flavors.
Can I book a refundable hotel in Shepherdstown?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Shepherdstown by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Shepherdstown with Expedia?
Expedia makes it easier to plan your Shepherdstown trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Shepherdstown?
The best choice depends on your travel style. Hotels in Shepherdstown can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Shepherdstown trip on Expedia?
Once you've booked your Shepherdstown trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Shepherdstown trip?
Expedia offers customer support before, during, and after your Shepherdstown trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Shepherdstown?
If it's your first trip to Shepherdstown, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Shepherdstown hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Shepherdstown hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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