Discover the Oldest Town in West Virginia

Written by Shreya Agrawal
Updated: November 9, 2023
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Key Points:

  • Shepherdstown originated due to a land grant from Lord Fairfax, one of the prominent landowners in colonial Virginia.
  • Shepherdstown was a thriving colonial town due to its strategic location along the Potomac River.
  • Modern-day Shepherdstown has earned a reputation as a hub for artists and art lovers.

Located along the banks of the scenic Potomac River in the state of West Virginia lies Shepherdstown. It is a town with lots of history and charm. Founded in 1762, Shepherdstown also holds the distinct honor of being the oldest town in West Virginia. Its story is one of resilience, transformation, and cultural significance.

The founder of Shepherdstown initially called it Mecklenburg to honor Charlotte of Mecklenburg-Strelitz, the Queen consort of King George III.

Shepherdstown’s Early History

Shepherdstown originated due to a land grant from Lord Fairfax, one of the prominent landowners in colonial Virginia. In 1734, Thomas Shepherd, an enterprising Scots-Irish immigrant, received a patent for the land that would later become Shepherdstown. It wasn’t until 1762, however, that the town was officially established from an act of the Virginia General Assembly.

The town’s name also has an interesting history of its own. Thomas Shepherd initially referred to it as “Mecklenburg” in honor of Charlotte of Mecklenburg-Strelitz, the Queen consort of King George III. However, he later decided that the town would be named after its founder, and thus, “Shepherdstown” was born.

Residential architecture, Shepherdstown, West Virginia

Shepherdstown still has several residents living in the small town.

©Jon Bilous/

A Thriving Colonial Town

Shepherdstown’s strategic location along the Potomac River also made it an essential hub for trade and commerce in the 18th century. The town quickly flourished as a center for milling, tanning, and manufacturing. Its growth was further increased by the establishment of the first permanent bridge across the Potomac in 1794, which connected Shepherdstown to the C&O Canal and, by extension, to the broader markets of the eastern United States.

The Role of Shepherd College

In 1872, Shepherdstown became home to Shepherd University. It is a vital institution that has an important role in the town’s history and development. Originally founded as a branch of the State Normal School of West Virginia, it later evolved into Shepherd College before attaining university status. Today, Shepherd University continues to be a cornerstone of the community, fostering education, culture, and the arts.

Shepherdstown’s Significance in the Civil War

The American Civil War also left a significant mark on Shepherdstown, as it did on many towns and cities throughout the nation. Shepherdstown found itself at the crossroads of history during the war, hosting several significant events including the ones below.

The Battle of Shepherdstown

On September 19-20, 1862, Shepherdstown witnessed conflict during the Battle of Shepherdstown, also known as the Battle of Boteler’s Ford. This was part of the larger Antietam Campaign, which had raged across the region. Union forces under General George McClellan clashed with Confederate troops led by General Robert E. Lee as they retreated from the Battle of Antietam in Maryland. However, the battle at Shepherdstown resulted in significant casualties on both sides.

Jefferson Rock on the Appalachian Trail in West Virginia with tree-covered hills in the background

Jefferson Rock on the Appalachian Trail in West Virginia with tree-covered hills in the background.

©Faith Hope Bryan/

A Hospital Town

Shepherdstown also became a critical center for medical care during the Civil War. Several buildings in the town became makeshift hospitals to tend to the wounded. Therefore, the tragic aftermath of battle left a mark on the town’s history, and echoes of this period is still visible through its many historical markers and preserved buildings.

The Aftermath

Shepherdstown’s involvement in the Civil War also shaped its character. Today, the town serves as a historical beacon, offering a glimpse into the turbulent times of the 19th century. Visitors can explore various Civil War sites, including the Elmwood Cemetery, where many Confederate soldiers still lie in their graves, as well as the Historic Shepherdstown Museum, which houses artifacts and exhibits related to the town’s wartime experience.

Shepherdstown’s Architectural and Cultural Heritage

Shepherdstown, West Virginia

Shepherdstown, West Virginia is the oldest town in the state.

©Acroterion / CC BY-SA 3.0 – License

Shepherdstown’s historic district also has a treasure trove of 18th and 19th-century architecture. The town’s commitment to preserving its heritage is evident in its well-maintained and picturesque streets lined with colonial and antebellum-era homes. Stately Georgian and Federal-style buildings and charming Victorian houses offer a lively aura to the town’s enduring history.

Mecca for Artists and Art Lovers

Beyond its architectural splendor, Shepherdstown has also earned a reputation as a hub for artists and art lovers. The town is also home to numerous galleries, theaters, and cultural venues that celebrate the arts. The Contemporary American Theater Festival, held annually at Shepherd University, also attracts theater enthusiasts from near and far. Therefore, the town’s vibrant arts scene has made it a haven for creative individuals as well as a must-visit destination for anyone seeking cultural enrichment.

Early morning along the Highland Scenic Highway, a National Scenic Byway, Pocahontas County, West Virginia, USA

Early morning along the Highland Scenic Highway, a National Scenic Byway, Pocahontas County, West Virginia.

©Malachi Jacobs/

Preservation and Restoration Efforts

The Shepherdstown Historic Commission and other local organizations have also played instrumental roles in the preservation and restoration of the town’s historic structures. These efforts have not only safeguarded Shepherdstown’s architectural heritage but have also helped maintain its unique character. It has therefore become a destination that transports visitors back in time.

Where Is Shepherdstown Located on a Map?

Shepherdstown lies in the northeastern corner of West Virginia, within Jefferson County. It is located approximately 70 miles northwest of Washington, D.C., and just across from the border with Maryland. The town’s position along the Potomac River brings it a lot of breathtaking natural beauty as well as accessibility, making it a popular destination for tourists and history buffs.

Shepherdstown’s Wildlife

While Shepherdstown’s rich history and vibrant culture often take the spotlight, the town is also a gateway to the natural beauty and diverse wildlife of West Virginia’s Eastern Panhandle. Since it lies in the Shenandoah Valley by the Potomac River, Shepherdstown has forests, fields, and waterways that provide a haven for a wide array of wildlife species.

Birds of the Sky

Birdwatchers and ornithologists find Shepherdstown to be a birding paradise. The town’s location along the Potomac River and near the Chesapeake and Ohio Canal offers a unique blend of habitats, attracting both migratory and resident bird species. Among the avian residents and visitors are:

  • Bald Eagles: These majestic raptors fly along the Potomac River, where they nest and hunt for fish.
  • Great Blue Herons: They often wade along the riverbanks and are known for their tall stature and graceful flight.
  • Warblers: Various warbler species pass through Shepherdstown during the spring and fall migrations and sing their melodious songs.
  • Red-shouldered Hawks: These birds of prey circle the skies, scanning for small mammals and amphibians in the town’s wooded areas.
  • Eastern Bluebirds: These charming and vibrant blue birds commonly perch on fence posts and nest boxes in the region.
Bald eagle in flight on isolated background

Bald eagle in flight on isolated background.


Mammals in the Shadows

The woodlands and fields surrounding Shepherdstown provide refuge for numerous mammal species. While many are elusive and prefer to stay hidden, others occasionally make appearances in the town’s outskirts. Some of the mammals you might encounter include:

  • White-tailed Deer: These graceful herbivores are a common sight in the area, especially during dawn and dusk.
  • Eastern Cottontail Rabbits: With their distinctive white tails, these small mammals can often be seen foraging in yards and open spaces.
  • Eastern Gray Squirrels: These tree-dwellers are known for their bushy tails and agile movements. They are a common presence in Shepherdstown’s neighborhoods and parks.
  • Opossums: Nocturnal and solitary, opossums are known for their distinctive rat-like tails and their ability to play dead when threatened.
  • Foxes: Red foxes and gray foxes are occasionally spotted in the region, especially in the more rural areas.
playful red fox cubs ( Vulpes ); young animals near the den, playing while vixen is out to hunt

Young red foxes are playful and learn to hunt through play.


Amphibians and Reptiles

The waterways and wetlands near Shepherdstown provide habitat for a variety of amphibians and reptiles. If you explore the banks of the Potomac River or nearby ponds, you may encounter:

  • Eastern Box Turtles: These slow-moving, terrestrial turtles can often be found in wooded areas and fields.
  • Northern Water Snakes: Non-venomous but often mistaken for venomous species, these snakes are expert swimmers and can be found near water sources.
  • Green Frogs: With their distinctive calls, these frogs are common in ponds and wetlands during the breeding season.
  • Eastern Newts: These small, aquatic salamanders can be spotted in pools and slow-moving streams.
American green tree frog with lush ginger foliage

American green tree frog with lush ginger foliage.


Insects and Arachnids

The natural landscapes around Shepherdstown teem with insects and arachnids. They play vital roles in local ecosystems. In the warmer months, you may come across:

  • Monarch Butterflies: These iconic butterflies can be seen during their incredible migration through the region.
  • Praying Mantises: Masters of camouflage, these predatory insects are often found in gardens and fields.
  • Orb-weaving Spiders: These spiders create intricate, circular webs and are skilled hunters of flying insects.
  • Fireflies: In early summer evenings, fireflies light up the night with their bright bioluminescence.
milkweed monarch butterfly

Despite their strong association with the milkweed plant, monarch butterflies are not the most its important pollinators.

©Nancy Bauer/

Conservation Efforts

Efforts to conserve and protect Shepherdstown’s natural habitats and wildlife are still ongoing. Local organizations and nature enthusiasts collaborate to maintain the region’s biodiversity and preserve its ecological balance.

Modern Shepherdstown

Shepherdstown’s role as an educational and cultural center continues to play a significant role in the region. Shepherd University, with its diverse academic programs and cultural events, remains a focal point of the town’s identity. Its art, music, and theater programs also contribute to the cultural vibrancy of Shepherdstown.

Tourism and Recreation

The town’s scenic location along the Potomac River, coupled with its rich history and cultural offerings, makes it a prime destination for tourists. Shepherdstown also serves as a gateway to the nearby Harpers Ferry National Historical Park as well as the Chesapeake and Ohio Canal National Historical Park. Hiking, biking, and water activities are very widely available in the surrounding areas.

Community and Festivals

Shepherdstown also has a very close-knit and welcoming community. Residents and visitors come together throughout the year to celebrate various festivals and events. The Contemporary American Theater Festival, the Shepherdstown Street Fest, and the Christmas celebrations in Shepherdstown are just a few examples of the vibrant community life that defines the town.

View overlooking the Trough Hampshire County West Virginia USA - Wooded gorge with Autumn foliage, distant creek bed between mountain ridges

View overlooking the Trough Hampshire County in West Virginia. Wooded gorge with autumn foliage, distant creek bed between

mountain ridges


©Bob Couperthwaite/


From its modest beginnings as a colonial trading post to its pivotal role in the American Civil War and its modern-day identity as an educational and cultural hub, Shepherdstown has evolved and thrived while maintaining a deep connection to its past.

Visiting Shepherdstown is like stepping back in time, where colonial-era architecture stands side by side with cultural institutions that celebrate the arts. Its commitment to historic preservation and its dedication to fostering a strong sense of community make it a unique and cherished destination in the Mountain State.

As Shepherdstown continues to evolve, it still carries with it the enduring legacy of those who have called it home throughout its history.

The photo featured at the top of this post is © Jordan Kercheff/

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About the Author

Shreya is a climate scientist. She also studies paleontology and evolutionary biology. She enjoys reading all kinds of literature and listening to rock music in her free time.

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