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The Halltown Union Colored Sunday School, also known as the Halltown Memorial Chapel, in Halltown, West Virginia, was built in 1901 in the Gothic Revival style. The stone chapel was built by and for the local African-American community on a small parcel of land donated by Daniel B. Lucas from his Rion Hall estate, next to the Halltown Colored Free School. The non-denominational Sunday School operated until 1967, although the building continued in use for weddings and funerals. In 1982 a committee was formed to restore the building, which was carried out the next year.It was listed on the National Register of Historic Places in 1984.

The Halltown Colored Free School in Halltown, West Virginia was built in 1870 to educate children from the African-American community in Halltown. The school was racially segregated from local schools for whites, in accordance with the laws of the time. It functioned in that capacity until 1929, when it was converted to a residence. The school is to the left and behind the Halltown Union Colored Sunday School, and is owned by the same community organization.It was listed on the National Register of Historic Places in 2004.

Halltown is an unincorporated community on land that was originally owned by William Hall along Flowing Springs Run in Jefferson County, West Virginia. Halltown is located off U.S. Route 340 on West Virginia Route 230 between Charles Town and Bolivar. A few houses, a fork in the road, a tiny post office, and the large Halltown Paper Plant are the distinguishing features of the community.

Rion Hall is a late Federal style house near Halltown, West Virginia. Built in 1836, it consists of a three-story brick house with a two-story kitchen wing connected by a wood hyphen. The house was used as a headquarters for General Philip H. Sheridan during the American Civil War. The house was built in 1836 by William Lucas. Lucas was the son of Robert and Sarah Rion Lucas, and was born at Cold Spring. In 1838, Lucas was elected to the United States House of Representatives, serving a total of three terms. At William Lucas' death, the property passed to his son, Daniel Bedinger Lucas, a lawyer and a poet, who was briefly appointed to the US Senate by the Governor of West Virginia, but not seated. With Daniel Lucas' death the property passed to Virginia Lucas, whose accidental death in 1929 left the house vacant for ten years. In 1938 the house changed hands and underwent renovation.

Blair is an unincorporated community on the Shenandoah River in Jefferson County, West Virginia, United States. Blair lies along County Route 23.

Media Farm is a farm complex near Charles Town, West Virginia that dates to 1780, and has remained in the same family ever since. The property was acquired by Charles Yates, an English immigrant, from Thomas Rutherford. In the twentieth century, author Julia McDonald Davis spent her childhood summers at the farm. Her father, who visited the farm frequently, was lawyer, diplomat and presidential candidate John W. Davis. The original house was a log structure, with a stone addition added in 1790. The house grew and its present appearance is Gothic Revival. During World War I several small tenant houses were built on the farm to house "farmerettes," who were city women brought from urban areas to assist farmers whose labor force had gone to war.

Millville is an unincorporated community on the Shenandoah River in Jefferson County, West Virginia, United States. According to the Geographic Names Information System, Millville has also been known as Keye's Switch, Keyes Switch and Milville.

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.

Reedson is an unincorporated community on Shepherdstown Pike (West Virginia Route 230) in Jefferson County, West Virginia, United States. Reedson lies between Uvilla to its North, and Halltown to its South.

Hollywood Casino at Charles Town Races is a casino, hotel and thoroughbred horse racing complex located in Charles Town, West Virginia, 60 miles (97 km) northwest of Washington D.C. It is owned by Gaming and Leisure Properties and operated by Penn Entertainment.

Engle is an unincorporated community in Jefferson County, West Virginia, United States, originally known by the names of Millers Mill, Striders Crossing, Keller, and Engles Switch before its post office's name changed to Engle in 1910. The community was named after Frank Engle, the proprietor of a lime kiln.

Jefferson High School is a high school located in the lower Shenandoah Valley in Shenandoah Junction, West Virginia. It was established in the fall of 1972, when the county combined Charles Town, Harpers Ferry, and Shepherdstown High Schools. It remained the only high school in Jefferson County until the fall of 2008. In-county rival, Washington High School, opened for the 2008–09 school year, splitting the Jefferson student body. Jefferson's total enrollment is 1,400. Jefferson's baseball program is the most decorated in West Virginia. The Cougars have won 12 state championships, most recently winning back-to-back titles in 2015-16. John Lowery has headed the program since the school's opening. He owns more than 1,330 wins and has led the Cougars to 45 straight 20+ win seasons. Jefferson's softball team won its first state title in 2022. The Cougars' boys track team has won six state championships, including four straight from 2010-2013. Girls track (2009 and 2021), boys tennis (1992), cross country (2011) and girls soccer (2007) have also won state championships. Notable graduates include former NFL wide receiver James Jett and former NFL safety Dewey McDonald and MLB first-round draft pick Josh Cenate. The Jefferson "Cougar" Marching Band, under the direction of Mr. J.P. Lynch Jr., is recognized as one of the top bands in West Virginia. The band has over 175 student musicians, and in 2012 the band was awarded first place in the Tournament of Bands (TOB) championships. A notable achievement includes the honor of marching in the Cherry Blossom Festival in Washington D.C. in April of 2013, 2015, and 2022. The Jefferson High School Symphonic Band was also named The West Virginia Honor Band in 2011, 2013, 2015, 2017, 2019, and 2022.