West Virginia's Oldest Town and Its Beautiful Architecture

European settlement in what is now known as Shepherdstown goes back to the early 1700s when German immigrants moved to the area from Pennsylvania. However, the official layout of the town did not occur until the town’s namesake, Thomas Shepherd, came to call the area home. At the time of its official incorporation in 1762, it was known as Mecklenburg; it was called Shepherd's Town after 1798, with the current spelling becoming standard after the Civil War.

The community preserves its history through the many old structures that remain standing along its bustling streets. Some of the most notable include Rumsey Hall (aka the Entler Hotel), Fruit Hill (aka the Robinson-Andrews-Hoxton House), and others in and around the city’s borders. Most are well-preserved and retain at least parts of their original construction, with some homes and structures dating back to the 1700s. From the yearly festivals, including a month-long Christmas and holiday festival beginning after Thanksgiving, to the artistic event known as StreetFest, there is no shortage of experiences to be had in this gorgeous small town.

Cultural Heritage

Sharing the spot as the oldest town in West Virginia — the town of Romney was incorporated on the same date: December 23, 1762 — is unique in itself, but Shepherdstown is so much more than just this. It also has many other features and aspects of its past that make it stand out amongst its neighboring communities. First, legend has it that during the early years of the United States, George Washington actually considered the beautiful town for the nation’s capital. Second, Shepherdstown saw the very first steamboat demonstration. In 1787, the inventor James Rumsey hosted the first successful steamboat demonstration right in town on the Potomac River, establishing Shepherdstown as a forward-thinking location early in the nation’s history. The community was also home to the state’s (i.e., Virginia's) first newspaper, publishing the local Potomac Guardian and Berkley Advertiser in 1790 by Nathaniel Willis. The newspaper served as a vital source of revolutionary fever during the American Revolution, reporting on the successes of the Continental Army. In fact, Willis participated in the Boston Tea Party.

Historical Museum

The Shepherdstown Historical Museum houses a little bit of everything from the town’s history. In fact, the building that houses the museum was once a town hotel known as the Entler Hotel, which is one of the oldest buildings in the community dating back to 1786. Although the original structure sadly burned down in 1912, the foundation of the hotel remains where the new building stands. As such an old town structure, it’s home to legends, ghosts, history, and artifacts. In particular, those hoping to encounter the old hotel’s ghostly visitors should consider checking out one of the rooms upstairs where, according to the hotel, guests claim to spot the ghost of William Payton Smith who was killed in a duel there in 1809. Up there, visitors are also likely to lay eyes on some old artifacts, like the Sheetz rifles and a copper kettle that belonged to Mary Tyler Moore’s ancestor, Conrad Schindler. Folks can also see an old mail carriage and other historic items, including Native American tools.

Shepherd’s Mill

One of Shepherdstown’s oldest standing structures is Shepherd’s Mill, built in 1738 by Thomas Shepherd, Sr. Today, a local couple owns the property, meaning that while it is on the historical register it is technically privately owned. According to the Shepherdstown Chronicle, the site's current owners are striving to preserve the mill and the 40-foot-diameter Fitz Water Wheel Company steel overshot water wheel which makes the site so iconic. The family hosted events in the past, allowing visitors to catch a glimpse of this old mill and potentially donate to their endeavors. Shannon Thomas, who owns the property along with her husband, Adam, is a local painter and helped direct the design and updates to the site to retain the original beauty while also giving it modern convenience. In April 2024, the family opened the location to the public and hosted the “A View to a Mill” art exhibit and they plan to continue hosting such events.

Walk the Beautiful City Trail

Although Shepherd’s Mill is by far one of the most amazing local historical attractions, there is an entire historic district to enjoy while traversing its winding streets. The city boasts a charming self-guided walking tour for those who wish to take in some of the community's best views. The trek takes explorers down West German Street, New Street, and others, with numbers posted along the way to guide travelers. While following the posted guidance is a great way to ensure no landmark is missed, it is not the only way to enjoy the trail. Some of the notable spots include places where residents have decorated their homes in a traditional style, including businesses and a few homes featuring leaded glass. Other notable features in these homes include cast iron decor made by the George L. Mesker and Company, located in Evansville, Indiana, a popular metal-making company in its day.

Folks can also take note of the “horse stones” along the roadway. These historic metal markers go back close to 200 years in the town and once served as a vital part of local transportation. Since horse and carriage were the main way to travel back in the day, these horse stones allowed people to mount and dismount with ease, and they still stand strong on the sides of the streets of Shepherdstown. Lastly, walkers can also enjoy the view of old water pumps standing outside of some residences and businesses, where thirsty travelers used to be able to stop and refresh themselves after paying a small fee to the homeowners.

BooFest, Christmas, StreetFest, and S'More

Every year, the streets of Shepherdstown are filled with monsters, witches, and goblins as the locals set out to trick-or-treat. German Street is a particularly popular spot for anyone hoping to glimpse some of the more seasonal decorations and displays. The festival spans most of the month of October and typically includes street vendors selling handmade goods and crafts, dancing, music, and cultural events that celebrate the community’s reputation as one of America’s most haunted towns. The BooFest Facebook page is a great place to learn about what to expect each year, since events and festivities vary.

Furthermore, every year the streets of Shepherdstown light up with festive splendor. The holiday and Christmas activities begin as soon as Thanksgiving ends, meaning visitors can expect to indulge in holiday-themed activities for nearly an entire month. The activities usually start with the Christmas Tree Lighting ceremony the day after Thanksgiving at McMurran Hall and also includes a festive bonfire and storytelling from Mrs. Claus. Sometimes the event also sees some new faces and guests, like the Grinch, Ebeneezer Scrooge, and other holiday favorites who make the season that much better.

The festivities don’t end there, either. There are events all month long up until, and sometimes even a little after, Christmas. Events shift and change pretty much every year, so it is best to review the relevant websites and social media pages before planning a visit, but there are some awesome highlights from past years that are sure to see a repeat in the future. To name a few, the Shepherdstown Kiwanis Club sells scrumptious chili at the War Memorial Building on German Street, and the fire department hosts a bonfire where folks can make s'mores.

StreetFest is an annual event that brings the whole town together and welcomes folks from all around the country to get a taste of Shepherdstown. It began back in 2005 and takes place every year, typically in late June. Some of the proceeds from the event go to support local and regional nonprofits, meaning that by purchasing items and supporting local artisans, visitors are also helping to support charity. Anyone hoping to enjoy the historic streets of Shepherdstown while exploring the various artistic vendors selling from their booths is sure to love this festival.

Closing Thoughts

Shepherdstown provides visitors with a unique glimpse into the early history of westward expansion. Back when the community first began, there was little more in the area than some woodlands, flowing rivers, and records of native tribes and their settlements. Today, Shepherdstown has grown into a vacation town, where folks come from all over to experience the country’s early days at historic sites and indulge in the modern artistic expression visible on every street corner. The annual festivals are the cherry on top, making every trip memorable and allowing guests a chance to see the tight-knit community at work.