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$178 per night from 23 Nov to 24 Nov
NZ$178
23 Nov - 24 Nov
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 ...
7.8/10 Good! (199 reviews)
Excellent stay!

Reviewed on 13 Nov 2025

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

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown WV
The price is NZ$193 per night from 1 Dec to 2 Dec
NZ$193
1 Dec - 2 Dec
includes taxes & fees
Stay at this cabin in Shepherdstown. Enjoy free Wi-Fi, a garden and patios. Popular attractions Rumsey Monument and Scarborough Library are located nearby.
9.8/10 Exceptional! (63 reviews)
Cabin was so so cozy!

Reviewed on 24 Oct 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$153 per night from 7 Dec to 8 Dec
NZ$153
7 Dec - 8 Dec
includes taxes & fees
Stay at this 3-star business-friendly hotel in Frederick. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,184 reviews)
Our room was very clean, and huge!! Staff was great!! Overall great experience. Would definitely stay again!!

Reviewed on 12 Nov 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 WV
Stay at this cabin in Shepherdstown. Enjoy free Wi-Fi, a garden and patios. Popular attractions Rumsey Monument and Scarborough Library are located nearby.
9.8/10 Exceptional! (63 reviews)
Cabin was so so cozy!

Reviewed on 24 Oct 2025

❤️ Secluded 1940s Romantic Tiny House on the River
Hidden Gem in the woods with hot tub

Hidden Gem in the woods with hot tub

Berkeley Springs
Stay at this cabin in Berkeley Springs. Enjoy free WiFi, a pool table, and patios. Popular attractions Berkeley Springs Antique Mall and Ice House are located ...
9.4/10 Exceptional! (86 reviews)
Beautiful spot. Relaxing.

Reviewed on 28 Oct 2025

Hidden Gem in the woods with hot tub
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! (59 reviews)
Love to relax here, usually a two weeknight stay, always clean and welcoming.

Reviewed on 6 Nov 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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