SE Corner of New and Princess Sts. One of the two public schoolhouses in town built by the state of Virginia in 1848, it continues to serve the cause of education as office space for Shepherd University professors. It is believed to be the oldest free schoolhouse in West Virginia.

SE corner of Princess and German Sts. Owner J. Matt Tolliver seems to have been the downtown area’s first successful Black businessman. His name appears in the town records during the years 1877 to 1908. After his popular restaurant burned in 1894, he built this brick building, where he ran a hotel and ice cream parlor. From 1899 to 1909 the town granted him an annual hotel license.

203 E German St, adjacent to the Yellow Brick Bank. A complex of three structures built for the Shepherd family as a town home, including a small rectangular brick building (which served as a doctor’s office from c. 1850 to 1890), a carriage house (converted into a tea room and tourist inn c.1920), and a Greek Revival brick house with iron grill work on the front said to have been brought from New Orleans by a member of the Shepherd family. Author Willa Cather spent a summer at the Gray Lodge working on a novel.

Historic Shepherdstown Museum is located in the former Entler Hotel. The museum details the history of Shepherdstown and houses many historical artifacts crafted by local artisans. Rooms are arranged to reflect the history of the community at different periods, ranging from the colonial era to the 20th century. At lunchtime on weekdays, local historians present oral accounts of the town's history. The museum also features an archives room for genealogical and historical research. The working replica of James Rumsey’s steamboat is housed in a boathouse on the museum’s grounds.

Located in the heart of Shepherdstown, the Shepherdstown Public Library was built in the 1800s as a market house, offering local farmers a sheltered place to sell their wares. It has also been home to the fire department, the town council offices, a butcher shop, a school, and the local jail. Today, it is the home of a thriving library.

Between E German and E High Sts., on Audrey Egle Dr. The Norfolk and Western Railroad built the passenger station in 1909. Waiting rooms and rest rooms were segregated. After nearly a half century of service, passenger traffic ended in 1957 and the station closed, to be used by the railroad for storage. In 1996 the railroad deeded the passenger station to the town for $1.00, and the building was restored and redesigned as a multiple use facility.

This limestone home built in 1790 was constructed for the Yeasley family. The home is older than the majority of brick structures in the area. Revolutionary War veteran Michael Yeasley and his family were German immigrants and a part of the original group of settlers in Mechlenburg, what is now Shepherdstown. Yeasley was a dedicated member of the German Reformed Church and organized the purchase of church bells for the Christ Reformed United Church of Christ.

126 W German St. Abutting Bedinger’s law office, it was Lindsey’s Tavern in 1800. By the mid 1800s it had become the site of the flourishing general store of John McEndree.

131 W German St. The Opera House replaced a one hundred year old building in 1909. Here moving pictures were shown continuously until 1956. Thirty-five years later, after extensive renovation, it reopened as a movie theater. It is currently used as a venue for both film and live music.

SE corner of Church and High Sts. The “Old English Church” began as a log cabin in 1745. A stone structure called the Mecklenburg Chapel replaced the original building in 1769. Though it has gone through several renovations, the basic structure of 1769 still remains. It is among the earliest surviving church buildings west of the Blue Ridge Mountains.

This historic bed and breakfast was built as a parsonage for St. Peter’s Lutheran Church in 1868. The Federal-style home served the church in this capacity until 1936, when the property was sold to Halvard Wanger and Sarah Elizabeth McFetridge, a husband-and-wife team of physicians who expanded the building to provide space for examination rooms and offices. In 1983, Ed and Carol Ringroot purchased the property and converted it into a bed and breakfast named in honor of town founder Thomas Shepherd.

From the corner of Princess and High Sts, N Princess makes a steep descent to the Potomac. Town Run falls here through a steep ravine where once gristmills, sawmills, manufacturing mills and warehouses took advantage of the water’s power. The only building left is the tobacco warehouse, authorized by Virginia’s General Assembly in 1788. The large stone building perhaps replaced an earlier wooden structure c.1800.

at the bottom of N Princess St. At the rivers edge, one stands at the border between West Virginia and Maryland. Here too is the former ferry landing, still in use as a boat ramp. The old piers in the river supported several bridges from 1849- 1936. The former bridge tollhouse, built in 1850, remains as a private residence.

This is marker #3 in a series of obelisks erected in 1910 by the Jefferson County Camp, United Confederate Veterans to mark locations of engagements and other significant Civil War events in Jefferson County. This obelisk represents the numerous events that occurred in and around Shepherdstown during the Civil War and the men from Jefferson County who served in the Confederate military.

Located along the Chesapeake and Ohio Canal, these historical markers share the history of Shepherdstown and its role in the Civil War. The marker of the left offers a general history of Shepherdstown from its Native inhabitants and growth as a stop along the C&O Canal to the history of the town during the Civil War. The marker on the right offers a detailed history of the 1964 Confederate raid of Jubal A. Early. Early's men crossed Blackford's Ford near this marker as part of the Confederacy's third and final attempt to invade Maryland. Although Early's raid led the Union to send troops to the area, it did not significantly alter the Union's offensive in Virginia as Confederate leaders had hoped.

One of the key turning points of the Civil War, the Battle of Antietam began at dawn on September 17, 1862, near Sharpsburg, Maryland. Neither side was able to claim a decisive victory and both endured tremendous casualties. Antietam became the bloodiest one-day battle in American history, with more than 23,000 casualties. Confederate General Robert E. Lee was forced to withdraw from the field due to his losses, ending his first invasion of the North. Although Union General George B. McClellan decided that his forces were too decimated as to pursue Lee's Army, the battle ended with General Lee's Army retreating to Virginia. President Abraham Lincoln had hoped for a Union victory before announcing his Preliminary Emancipation Proclamation. While Antietam was equally devastating in terms of casualties, the fact that Lee's Army had withdrawn from Pennsylvania allowed Lincoln to announce his intention to end slavery at a moment when confidence in the Union cause had been restored. Lincoln's declaration would appear as a thoughtful and deliberate measure rather than a desperate act by a President who was attempting to use an Executive Order to strike a blow to the South that his armies could not deliver.

The Kennedy Farm served as abolitionist John Brown's headquarters as he planned his October 1859 raid on Harpers Ferry. The farmhouse was originally built by Robert F. Kennedy in the 1850s and sat empty after his death in the spring of 1859. John Brown and his followers arrived in the area on July 3, 1859. Looking for a place to stage their upcoming raid on nearby Harpers Ferry, they presented themselves as cattlemen from New York who were looking for property. A local resident suggested the now-vacant Kennedy farm and Brown and his men leased the property and spent a total of three and a half months in the Kennedy Farmhouse. Today, the farmhouse has been entirely restored by area preservationists with the support of state and federal funds. The Kennedy Farm was designated as a National Historic Landmark and is also on the National Register of Historic Places.

The Pry House Field Hospital Museum is located on the Antietam Battlefield in the historic Pry House, which was the home to Union Commander General George B. McClellan and Medical Director Dr. Jonathan Letterman during the battle. The exhibits include a recreation of an operating theater, interpretive panels, objects relating to the care of the wounded, the history of the Pry House and family, and information on the revolutionary system of evacuation of wounded created by Dr. Letterman during the battle, which is still in use today.

Built in 1832, Van Metre Ford Bridge was constructed to improve transportation between the Virginia communities of Alexandria and Bath. Now located in West Virginia, the historic bridge spans Opequon Creek and was one of many transportation projects that resulted from the migration of people from eastern communities to Appalachia during the early 1800s. At the time of construction, stone bridges like this one were becoming more rare as rapidly-growing communities opted for wooden bridges that were cheaper and faster to build. The Van Metre Ford Bridge was in use by vehicles until a new, three-lane bridge was built next to it in 2016. Today, the historic bridge is open for pedestrian use. At the southeastern end of the bridge, a highway marker features the history and significance of the structure.

The Battle of Harpers Ferry took place September 12-15, 1862, during the American Civil War. As Confederate General Robert E. Lee invaded Maryland, he also hoped to capture the Union garrison stationed in Harpers Ferry, then part of Virginia. To achieve this, he divided his force and sent General Thomas "Stonewall" Jackson to deal with the garrison while his main force continued in Maryland. Jackson's successful capture of Harpers Ferry allowed the Confederates to gain strategic ground and access to supplies. It resulted in the largest United States surrender in the Civil War, with over 12,000 Union soldiers taken prisoner. The battlefield is now protected by the National Park Service and Civil War Trust.

Until 1824, Harper's Ferry relied on the ferry of the same name for transportation across the Potomac River. Since then, five bridges have been built over the Potomac, though only two are still standing. These bridges would be one of the factors that made Harpers Ferry into one of the most sought after positions in the Civil War, where it changed hands eight times between 1861 and 1864. The crossing was added to the National Register of Historic Places in 1978.

Harpers Ferry National Historical Park is nestled at the confluence of the Shenandoah and Potomac Rivers in West Virginia with views of Maryland and Virginia. Visitors can cross the Potomac River and hike to the peak of Maryland Heights that overlooks Harpers Ferry. Harpers Ferry National Historical Park houses Storer College, buildings involved in John Brown's Raid, and a Civil War battleground.

Also known as the Battle of Hainesville and the Battle of Falling Waters, is the Battle of Hoke’s Run. An early battle of the Civil War, the Battle of Hoke’s run was an initial skirmish in the Manassas Campaign. Famous Union and Confederate generals fought in this speedy battle that had farther reaching implications for the small victory the Union army gained on July 02, 1861.

The Doughboy statue honors the infantry soldiers from Martinsburg and throughout Berkely County who served in the United States Army during the first World War. The statue was dedicated on New Year's Eve on 1925 and built by donations from local citizens. Many of these donations were secured through the efforts of the women of the American Legion Auxiliary, who solicited donations from local residents throughout the county on behalf of the Berkeley County Memorial Association.

The Old Opera House is a historic performing arts center in Charles Town. It opened in 1911 under the direction of Annie Packette, a prominent local who sought to bring more culture to the community. The opera house hosted a number of plays, vaudeville shows, minstrels, sporting events, and film screenings before closing in 1948. In 1973 the building was donated to the newly-formed Old Opera House Theatre Company which worked to restore and refurbish the old theatre. It reopened to the public in 1976 and today hosts a variety of plays along with an art gallery and acting, dance, and singing lessons. The Old Opera House was added to the National Register of Historic Places in 1978.

Beaver Creek Museum is a historical two room school house. The school house dates back to 1904 and includes many items from the time period.

The construction of the earliest parts of the Snodgrass Tavern was started in 1742, though the builder is unknown. The structure was built in parts and is one of the oldest buildings in West Virginia. The humble building has seen several high profile guests over its long operational life, such as George Washington. It served as a tavern until 1847, when the last Snodgrass owner refused to serve alcohol. After it was sold, it has served as a private residence ever since.

Located in Bunker Hill, West Virginia, there is a cabin of the first known white resident of West Virginia, Morgan Morgan. In 1726, Morgan Morgan came to Western Virginia with his wife and five children. Morgan built his cabin between 1731-1734, and it consists of one room with a loft above it.