Shepherdstown Travel Guide

Tourist Guide

Shepherdstown showing street scenes, heritage elements and a small town or village
Shepherdstown
Shepherdstown featuring an administrative building and heritage architecture
Shepherdstown featuring a small town or village, signage and street scenes
Shepherdstown which includes heritage architecture and an administrative building

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, familiarise 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.

Quality Inn Shepherdstown

Quality Inn Shepherdstown

2.5 out of 5
70 Maddex Square Dr, Shepherdstown, WV
The price is NZ$182 per night from 7 Sept to 8 Sept
NZ$182
7 Sept - 8 Sept
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 ...
7.6/10 Good! (158 reviews)
"a Pool would be nice."

Reviewed on 10 Aug. 2025

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

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
The price is NZ$238 per night from 14 Sept to 15 Sept
NZ$238
14 Sept - 15 Sept
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! (57 reviews)
Peaceful, Clean & Convenient to Area Attractions
"My second say at this cabin, definitely want to visit again. The cabin is private, clean and cozy perfect base of operations for day trips around the area."

Reviewed on 28 Jul. 2025

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

Country Inn & Suites by Radisson, Frederick, MD

3 out of 5
5579 Spectrum Dr, Frederick, MD
The price is NZ$158 per night from 24 Aug to 25 Aug
NZ$158
24 Aug - 25 Aug
includes taxes & fees
Stay at this 3-star business-friendly hotel in Frederick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,079 reviews)
"Very nice property, very convenient with late check in"

Reviewed on 14 Aug. 2025

Country Inn & Suites by Radisson, Frederick, 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
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! (57 reviews)
Peaceful, Clean & Convenient to Area Attractions
"My second say at this cabin, definitely want to visit again. The cabin is private, clean and cozy perfect base of operations for day trips around the area."

Reviewed on 28 Jul. 2025

❤️ Secluded 1940s Romantic Tiny House on the River
Welcome to this patch of serenity on the river's edge, to this hideaway.

Welcome to this patch of serenity on the river's edge, to this hideaway.

Shepherdstown
Book a stay at this family-friendly vacation home in Shepherdstown. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the property condition ...
9.8/10 Exceptional! (63 reviews)
Fabulous stay!
"We really enjoyed staying here. Kitchen was well stocked. Beautiful porch with a gorgeous view. Living area is nice and open. The inly feedback I would have is that the master bed does not have much support, so my back was a little sore in the mornings after sleeping on it. Overall would absolutely ..."

Reviewed on 23 Jun. 2025

Welcome to this patch of serenity on the river's edge, to this hideaway.
Private, light filled retreat space...
     with your own pickleball court!

Private, light filled retreat space... with your own pickleball court!

Berkeley Springs
Stay at this cabin in Berkeley Springs. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attractions Ice House and Berkeley ...
10/10 Exceptional! (41 reviews)
"Fantastic place to stay. Beautiful property on a secluded lot with pleasant views of woods and mountains all around. For two people, there is more than enough space for anything you are likely to want to do. The kitchen is modern and well-stocked and the furniture is all wet comfortable.About a 12-minute ..."

Reviewed on 8 Aug. 2025

Private, light filled retreat space... with your own pickleball court!
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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