West Virginia's Oldest Town Is An Artsy Mountain Gem Often Called One Of 'America's Coolest'

When you think of cool, artsy mountain towns, does Shepherdstown, West Virginia, come to mind? If not, you're missing out on incredible experiences in one of the state's oldest cities. Settled in the 1700s, Shepherdstown invites travelers to explore a curious collection of historical sites, art galleries, and cultural festivals. In a region home to one of the strangest extreme sports and regarded as an iconic fall hiking destination, this spot manages to steal the show as one of America's coolest small towns.

Located on the Potomac River by the West Virginia-Maryland border, this Eastern Panhandle village of roughly 1,600 residents offers year-round adventure. Warm summers in the 70s and 80s are great for tubing or boating down the Potomac, and the spring season decorates local streets with blooming flowers. As the weather cools, Shepherdstown also enjoys stunning fall foliage and light-to-average winter snowfall for vacationers to appreciate. Visitors will also find the town's calendar packed with festivals and events, from the Halloween BooFest to the springtime American Conservation Film Festival.

Shepherdstown's history stretches back before the United States officially became a country. Chartered in 1762 and settled even earlier, the region showcases an enviable collection of local landmarks. Plan your trip around this list of the best historical sites in Shepherdstown.

Your journey through years past begins at the Historic Shepherdstown Museum. Founded in 1983 to help preserve the town's history, the museum features fascinating artifacts and archives available to visit by appointment. Across the street sits another historical spot, the Mecklenburg Inn. Largely unchanged since around 1793, the Mecklenburg Inn (aka The Meck) still welcomes overnight guests and diners. Next, walk around the corner to reach McMurran Hall, a Greek Revival-style building built in 1859. Originally meant to be the town hall, this landmark has been used by Shepherd University since 1871. Just steps away, Shepherdstown visitors can see Saint Peter's Lutheran Church, a Gothic Revival structure with a history dating back to the late 1700s. Last but not least, walk toward the river to see a site some call the birthplace of the steamboat. On the banks of the Potomac River, travelers will find James Rumsey Monument and Park, a landmark honoring a pioneer in steamboat technology.

The artsy, creative side of Shepherdstown helps make this destination one of America's best small towns. For live performances and film screenings, visit the Shepherdstown Opera House, a community arts hub since 1910. Find more theatrical productions at the Black Box Arts Center and Shepherd University Theater. For paintings, sculptures, and other artworks, check out Shepherdstown's art galleries. Get involved with events at The Bridge Gallery, view free exhibitions at Phaze 2, or take art classes at The Badgerhound. Shepherdstown's live music scene is also thriving at nearby bars and restaurants. Watch local performers and tour a Shepherdstown landmark by visiting O'Hurley's General Store for Thursday night jam sessions.

Travelers who visit Shepherdstown in summer or early autumn can also partake in several regional art festivals. In June, the city hosts StreetFest, an arts and crafts event full of food and live music. Come July, Shepherdstown celebrates the theatrical arts during the Contemporary American Theater Festival. In September, the wider Jefferson County area holds the Mountain Heritage Arts and Crafts Festival. For the cost of admission (buy tickets in advance for a discount), visitors can watch live musicians and peruse creations by local crafters.