Hollywood Casino at Charles Town Races

Shenandoah Downs was a five-furlong horse-racing track located just outside the eastern limits of Charles Town, West Virginia, United States, that operated from 1959 through 1975. When it opened it featured night racing, a novelty at the time, initially running harness races. After operations began, the owners asked the West Virginia Racing Commission to allow thoroughbred racing, competing with the day races at adjacent Charles Town Races. Following litigation, the request was granted and the track converted to nighttime flat racing. Nighttime racing followed at Charles Town in 1965 and the adjoining tracks were allotted roughly equal numbers of racing days. In 1972 Charles Town was purchased by the owners of Shenandoah Downs. In 1976 Shenandoah Downs was closed down. In 1978 after both tracks were sold to a new owner, Shenandoah Downs briefly reopened. The Shenandoah Downs track was operated as a training track afterwards, until the site was developed. The grandstand remained until 2006 when it was demolished. An unrelated track in Woodstock, Virginia by the same name began operations in 2016, running annual harness racing meets, and moving to a two meets a year in 2023.

Belvedere, also known as Belvidere, was built near Charles Town, West Virginia by Magnus Tate II in 1807. The Federal style mansion is situated at the end of a tree-lined driveway and commands a sweeping view of the Blue Ridge Mountains. The house grew from the original "kitchen house" section to a formal three-bay brick main house built in 1824 by Magnus's son WIlliam, which were separate until they were connected in 1939.The site was inhabited by the Tate family from the 1760s. Magnus Tate II (1732-1808) was a founder of Charles Town. His four sons were all born at Belvedere. Magnus Tate III (1767-1823) served in the Virginia Assemby before serving from 1815 to 1817 in the U.S. House of Representatives. Belvedere passed to William Tate (1776-1818), and then to his son, George Tate II. The house passed out of the Tate family in 1882.

Charles Town Cave — also formerly known as Crystal Lake Cave and Lakeland Cave — is located in the center of Charles Town, West Virginia, United States. One entrance was in the cellar of a bakery (since demolished) and led down to a passage about 175 feet long to a large pool of clear water about 25 feet in diameter. Much of the cave is under the current Old Opera House building. The cave was discovered accidentally in 1906 and was for a time developed as a commercial show cave in the late 1920s and early '30s. Water sampling in 1997 showed the presence of petroleum contamination in the water.The cave is closed to the public. Rumors persist about other entrances to the cave in various Charles Town and Ranson buildings.

The Charles Town Mining, Manufacturing, and Improvement Company Building in Ranson, Jefferson County, West Virginia is a Romanesque Revival building that now serves as Ranson's City Hall. It was built for the Charles Town Mining, Manufacturing and Improvement Company (CMM&I) in 1891 as its headquarters. The CMM&I sought to develop industry in the area that in 1910 became the City of Ranson. The company was formed in 1890 by Roger Preston Chew, Frank Beck, Forrest W. Brown, T.C. Green, W.F. Lippitt, A.W. McDonald and B. C. Washington, with Chew as president. Using 850 acres (3.4 km2) of land purchased from the Ranson family, a planned community was laid out by D.G. Howell, a Washington, D.C. landscape architect and civil engineer. In 1891 the 3½ story headquarters was built, designed by J.C. Holmes. By 1893 the CMM&I was facing hard times, possibly as a result of the Panic of 1893, and the headquarters was sold to the Board of Education of Charles Town, and served as the white Charles Town High School from 1893 to 1912. The school was sometimes known as both the "Keyhole School,” due to its distinctive entrance, and as the Wright Denny School. In 1917 the Board of Education sold the school to former mayor Gerard D. Moore, and upon his death the property went to H.C. Getzendanner for $4500. Part of the building was used as a confectionery and the north half became the Ranson Post Office. In 1936 the City of Ranson bought the building for $3000 as its City Hall, although apartments occupied the upper floors until the 1970s.

The Downtown Charles Town Historic District comprises the commercial center of Charles Town, West Virginia. The district centers on Washington Street and includes the Jefferson County Courthouse and the New Opera House, themselves on the National Register of Historic Places. Other structures include the Market House, the Independent Fire Company building and the Post Office. A few very early buildings are included, such as the Sheetz House, dating to 1797. The town is significant as the scene of the trial of John Brown and as a contested town during the American Civil War. Charles Town is closely associated with the Washington family, as it was laid out by George Washington's brother Charles Washington. During the Civil War, there was fighting in the town itself on several occasions. In 1864, General Philip Sheridan used the Rutherford House at 417 East Washington Street as a headquarters for the Valley Campaign, meeting General Ulysses S. Grant there.

The Gibson-Todd House was the site of the hanging of John Brown, the abolitionist who led a raid on Harpers Ferry, West Virginia before the opening of the American Civil War. The property is located in Charles Town, West Virginia, and includes a large Victorian style house built in 1891. The house was built by John Thomas Gibson, who led the first armed response to Harpers Ferry during Brown's raid as commander of the Virginia Militia in Jefferson County. Gibson went on to serve as an officer for the Confederacy. After the war he was mayor of Charles Town. Among those present at Brown's hanging were Stonewall Jackson, John McCausland, J.E.B. Stuart and John Wilkes Booth. When the old Jefferson County jail was demolished, Gibson saved stones from the building and built a monument to the event on the property. The house post-dates Brown's hanging. The house was designed by Thomas A. Mullett, son of Alfred B. Mullett. Mullett also designed the New Opera House and the new Charles Town jail.

Ranson is a city in Jefferson County, West Virginia, United States. The population was 5,433 at the 2020 census. It is part of the northwestern fringes of the Washington metropolitan area.

The Jefferson County Courthouse is a historic building in Charles Town, West Virginia, USA. The building is historically notable as the site of two trials for treason: that of John Brown in 1859 (treason against Virginia), and those of unionizing coal miners from Mingo County, West Virginia (treason against West Virginia), a consequence of the Battle of Blair Mountain, whose trials were moved from the southern part of the state in 1922 as a result of a change of venue. It was designated a National Historic Landmark in 2023 for its role in the mining wars.

The Old Opera House is located in the Shenandoah Valley in Charles Town, West Virginia, once known as the New Opera House or simply The Opera House, is a restored theater, designed by T.A. Mullett of Washington, D.C., son of architect Alfred B. Mullett. The theater opened in 1911, bringing minstrel shows, vaudeville, touring theater groups, circuses and wild west shows to Charles Town. By the 1930s a projection machine was installed, but the theater closed in 1948. It has since re-opened as a community-supported performance space. The building consists of a two-story street front with offices on the second floor in an old apartment building, pre-dating the theater portion by about twenty years. The house and stage occupy the interior of the lot.

Charles Town is a city in and the county seat of Jefferson County, West Virginia, United States. The population was 6,534 at the 2020 census. The city is named for its founder Charles Washington, youngest brother of President George Washington. It is part of the northwestern fringes of the Washington metropolitan area.

The Harpers Ferry Armory, more formally known as the United States Armory and Arsenal at Harpers Ferry, was the second federal armory created by the United States government; the first was the Springfield Armory. It was located in Harpers Ferry, Virginia, which since 1863 has been part of West Virginia. It was both an arsenal, manufacturing firearms, and an armory, a storehouse for firearms. Along with the Springfield Armory, it was instrumental in the development of machining techniques to make interchangeable parts of precisely the same dimensions.The Armory was a long, narrow complex of buildings, located alongside the Baltimore and Ohio Railroad line on a strip of land alongside the Potomac River. The entrance was close to the center of town, with its train station and hotels, and the bridge, the B & O Railroad Potomac River Crossing. At its peak, just before the Civil War, the Armory had 400 employees.: 185 During the American Civil War, the Armory was destroyed and its equipment removed; it was not rebuilt. The only surviving building is its former fire engine house, known today as John Brown's Fort. As of 2021, it is not in its original location.

The Old Charles Town Historic District comprises more than three hundred structures, primarily residences, in Charles Town, West Virginia. In contrast to the mainly commercial Downtown Charles Town Historic District, the Old Charles Town Historic District includes many early houses, some of log construction. Later houses are in the Federal style, with Italianate and Greek Revival buildings. A number of Second Empire and Victorian homes are present. The most notable house in the district is Hunter Hill, the house of Andrew Hunter, chief prosecutor of John Brown. Built in 1820, the house was destroyed during the American Civil War by his Unionist cousin David Hunter, and was rebuilt in 1865.