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Gap View Farm, near Charles Town, West Virginia, is a historic farm complex built in 1774. The farm was placed on the National Register of Historic Places on January 9, 1997.

Aspen Hill is a farmhouse, built about 1840 near Charles Town, Virginia (now in West Virginia), by James G. Hurst, a middle-tier farmer and landowner, who sought to build a residence befitting his rising status. The house occupies a middle ground between the grand mansions of the landed gentry and the more humble dwellings of more modest farmers. The house lacks some of the details and craftsmanship present in more substantial houses.

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.

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.

Jefferson County is located in the Shenandoah Valley in the Eastern Panhandle of West Virginia. It is the easternmost county of the U.S. state of West Virginia. As of the 2020 census, the population was 57,701. Its county seat is Charles Town. The county was founded in 1801, and today is part of the Washington metropolitan area.

Shenandoah Junction is a census-designated place (CDP) in Jefferson County in the U.S. state of West Virginia's Eastern Panhandle. As of the 2010 census, Shenandoah Junction had a population of 703. It is located between Kearneysville, WV and Charles Town, WV off WV 9. Shenandoah Junction is home to Jefferson High School and West Virginia's oldest surviving wood-frame structure, the Peter Burr House, built around 1751. The land where Shenandoah Junction was built was part of the 392 acres (1.59 km2) granted by Lord Fairfax to Lewis Neil. The town was originally called Neil's, but the name was changed to Shenandoah Junction in 1881. The town owes much of its early growth to the coming of the Baltimore and Ohio Railroad in the 1830s, and the name refers to the junction of the B&O and Norfolk and Western Railway at the center of the community. Today, the Norfolk Southern Hagerstown Line (H Line), and the CSX Cumberland Subdivision lines intersect at the Junction.

Beall-Air, also known as the Colonel Lewis William Washington House, is a two-story stuccoed brick house in classical revival style near Halltown, West Virginia. It was the home of Colonel Lewis William Washington, great-great nephew of President George Washington and hostage in John Brown's raid on Harpers Ferry, West Virginia.The original house, now the rear portion of the house, is believed to have been built by Thomas Beall prior to 1800. Beall's daughter Elizabeth married George Corbin Washington in 1807. George Corbin was the grandson of Augustine Washington, half-brother of George Washington. The present front of the house was added in 1820.

The Peter Burr House was built between 1751 and 1755 near present-day Shenandoah Junction, West Virginia, making it one of the oldest houses in West Virginia. Burr, whose first cousin was Aaron Burr, was one of the first settlers in the area. It is the oldest surviving post-and-beam-construction house in West Virginia. The 9.5-acre (3.8 ha) property was acquired from Burr family descendants in the 1990s and has been under restoration by Jefferson County Historic Landmarks Commission.

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.

Duffields is a passenger rail station on MARC Train's Brunswick Line, in the community of Duffields, West Virginia. Since it is located in West Virginia, the station is maintained by the West Virginia State Rail Authority rather than by MARC itself. Between 1976 and 1981 this station was served by Amtrak's Shenandoah which traveled between Washington and Cincinnati.In 2015, a study began to look into the feasibility of replacing the station with a new station in nearby Ranson, West Virginia.

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.

Duffields is an unincorporated community in Jefferson County, West Virginia, United States. Duffields depot is the second oldest surviving B&O depot, named for the pre-Civil War landowner who constructed it (Richard Duffield), and has been on the National Register of Historic Places since 2007. No longer in railroad use, it is expected to become a museum. During the American Civil War, a Confederate infantry company (Company H of the 2nd Virginia Infantry) was recruited from the area. The depot became a strategic target, most famous for its capture by Confederate Capt. John S. Mosby on June 29, 1864, as well as a raid his Rangers made on a Union army pay train on October 14, 1864 (the "Greenback raid"). The modern community is served by the Duffields MARC Train station, located on the Brunswick Line. Services to Washington, D.C., and Martinsburg are provided on weekdays.