Shepherdstown

Travel Guide

Shepherdstown
Shepherdstown
Shepherdstown
Shepherdstown
Shepherdstown

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 Centre 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 Theatre 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.

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown WV
The price is CA $93 per night from May 21 to May 22
CA $93
CA $187 total
May 21 - May 22
includes taxes & fees
Stay at this cabin in Shepherdstown. Enjoy free WiFi, a garden, and patios. Popular attractions Rumsey Monument and Scarborough Library are located nearby.
9.8/10 Exceptional! (74 reviews)
Enjoyed my stay I appreciate the view and Rich.

Reviewed on Apr 13, 2026

❤️ Secluded 1940s Romantic Tiny House on the River
Quality Inn Shepherdstown

Quality Inn Shepherdstown

2.5 out of 5
70 Maddex Square Dr Shepherdstown WV
The price is CA $129 per night from Jun 3 to Jun 4
CA $129
CA $144 total
Jun 3 - Jun 4
includes taxes & 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 ...
8/10 Very Good! (230 reviews)
Breakfast was cold, not refreshed with new foods.

Reviewed on Apr 28, 2026

Quality Inn Shepherdstown
Graycliff Retreat:Unforgettable experience at this 11BR Estate;Game Room+Hot tub

Graycliff Retreat:Unforgettable experience at this 11BR Estate;Game Room+Hot tub

Shepherdstown WV
Stay at this castle in Shepherdstown. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Killiansburg Cave and Cress Creek Country ...
10/10 Exceptional! (1 review)
Beautiful area!

Reviewed on Sep 1, 2025

Graycliff Retreat:Unforgettable experience at this 11BR Estate;Game Room+Hot tub
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.
9.8/10 Exceptional! (74 reviews)
Enjoyed my stay I appreciate the view and Rich.

Reviewed on Apr 13, 2026

❤️ Secluded 1940s Romantic Tiny House on the River
Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance

Shepherdstown WV
Stay at this cottage in Shepherdstown. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Shepherdstown Opera House and Shepherdstown ...
9.4/10 Exceptional! (13 reviews)
Room condo in a great location

Reviewed on Apr 12, 2026

Quaint Mini Cottage in Shepherdstown - Walking Distance
Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views

Shepherdstown WV
Stay at this vacation home in Shepherdstown. Enjoy laundry facilities, balconies, and an in-room coffeemaker. Popular attractions Killiansburg Cave and Hagerstown ...
10/10 Exceptional! (18 reviews)
If you’re looking for a quiet getaway from big city living, this is the place! Not only does the house have amazing Potomac River water views, the house itself was clean, comfortable, and well-stocked with everything you need to enjoy a vacation. While it’s off the beaten path, it’s just a short ...

Reviewed on Apr 3, 2026

Exclusive Wooded Chalet w Magnificent River Views
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.

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