Mount Hebron Cemetery and Gatehouse

Old Stone Church (also known as the Presbyterian Meeting House) is a historic church at 304 E. Piccadilly Street in Winchester, Virginia. The church meeting house was constructed in 1788. Upon its completion, local Presbyterians began worshipping in the building. In 1800, the Winchester Presbytery officially established the congregation as the "Presbyterian Church in Winchester." The first pastor was the Rev. Dr. William Hill.The church building was added to the National Register of Historic Places in 1977.

The George Washington Hotel is a historic hotel located in downtown Winchester, Virginia. It was built in 1924 by The American Hotel Corporation, as part of their "Colonial Chain" of hotels. Like many hotels of the era, the property was built in close proximity of a B&O train station and was constructed to provide lodging to railroad passengers.

Frederick County Courthouse is a historic county courthouse located at Winchester, Frederick County, Virginia. It was built in 1840, and is a two-story, rectangular, brick building on a stone foundation and partial basement in the Greek Revival style. It measures 50 feet by 90 feet, and features a pedimented Doric order portico and a gabled roof surmounted by a cupola. Also on the property is a contributing Confederate monument, dedicated in 1916, consisting of a bronze statue of a soldier on a stone base.The building currently houses the Shenandoah Valley Civil War Museum.It was listed on the National Register of Historic Places in 2001. It is located in the Winchester Historic District.

Stonewall Confederate Cemetery is a subsection of Mount Hebron Cemetery in Winchester, Virginia, established in 1866 for 2,575 Confederate soldiers who died in battle or in the hospitals in and around the Winchester area. A monument over the mass grave of more than 800 unknown Confederate soldiers is at the center of the cemetery, and there is a section for each state member of the Confederacy. The plots are thus organized according to the home states of the fallen soldiers within. There are state monuments in most of the sections.

Winchester National Cemetery is a United States National Cemetery located in the city of Winchester in Frederick County, Virginia. Administered by the United States Department of Veterans Affairs, it encompasses 4.9 acres (2.0 ha), and as of the end of 2005, it had 5,561 interments. It is closed to new interments. The cemetery was used for burials of Union soldiers. The Stonewall Confederate Cemetery was for Confederate soldiers.

Winchester is the northwesternmost independent city in the Commonwealth of Virginia. It is the county seat of Frederick County, although the two are separate jurisdictions. The Bureau of Economic Analysis combines the city of Winchester with surrounding Frederick County for statistical purposes. As of the 2020 census, the city's population was 28,120.Winchester is the principal city of the Winchester, Virginia–West Virginia, metropolitan statistical area, which is a part of the Washington-Baltimore combined statistical area. Winchester is home to Shenandoah University and the Museum of the Shenandoah Valley.

The Winchester Historic District is a national historic district located at Winchester, Virginia. The district encompasses 1,116 contributing buildings in Winchester. The buildings represent a variety of popular architectural styles including Late Victorian and Italianate. They include residential, commercial, governmental, industrial, and institutional buildings dating from the 18th to mid-20th centuries. Notable buildings include the A.M.E Church (1878), Masonic Lodge and Gray and Eddy Building, First Presbyterian Church (1841, 1883), Farmers and Merchants Bank (1902), Frederick County Courthouse (1840), Grace Lutheran Church (1841, 1875), Friendship Fire Hall (1892), John Kerr School (1883, 1908), City Hall (1900), Lewis Jones Knitting Mill (1895), Tidball Residence (c. 1835), William F. Hottle Residence (c. 1880), McGuire Residence (c. 1820), and Robert Long House (c. 1930). Located in the district are the separately listed Thomas J. Jackson Headquarters, Fair Mount, Handley Library, Adam Kurtz House, and Daniel Morgan House.It was listed on the National Register of Historic Places in 1980, with boundary increases in 2003, 2008, and 2016.

The Patsy Cline Historic House at 608 S. Kent St., in a working-class neighborhood of Winchester, Virginia was the home from 1948 to 1953 of Virginia Patterson Hensley, who later became the country music star known as Patsy Cline. She moved out of the house when she got married at the age of 21 to Gerald Cline, but returned intermittently afterwards. The house was placed on both the Virginia Landmarks Register and the National Register of Historic Places in 2005, and a Virginia State Historical Marker was placed there about the same time. The house was designated a National Historic Landmark in 2021.

The Second Battle of Winchester was fought between June 13 and June 15, 1863 in Frederick County and Winchester, Virginia as part of the Gettysburg Campaign during the American Civil War. As Confederate Lieutenant General Richard S. Ewell moved north through the Shenandoah Valley in the direction of Pennsylvania, his corps defeated the Union Army garrison commanded by Major General Robert H. Milroy, capturing Winchester and numerous Union prisoners.

Fort Loudoun was a historic fortification of the French and Indian War, located in what is now Winchester, Virginia. The fort was built between 1756 and 1758 under the supervision of George Washington, then a colonel in the Virginia Regiment. It was named for John Campbell, 4th Earl of Loudoun, who commanded the British forces in North America for a time during the war. Washington and his militia regiment were headquartered at the fort for two years. The fort was a roughly square bastioned earthworks, whose extent spread across where North Loudoun Street runs.The property at 419 North Loudoun encompasses the historic heart of the fort, including a well dating to the fort's construction, and a portion of its northwest bastion. This area has been listed on the National Register of Historic Places. This property is now owned by the non-profit French and Indian War Foundation.

Handley Library is a historic library building located at 100 West Piccadilly Street in Winchester, Virginia, United States. Completed in 1913, construction of the Beaux-Arts style building was funded by a wealthy Pennsylvania businessman. The building serves as the main branch for Winchester's library system, the Handley Regional Library System. It was listed on the National Register of Historic Places (NRHP) and Virginia Landmarks Register (VLR) in 1969.

Adam Kurtz House, also known as Washington's Headquarters, is a historic home located at Winchester, Virginia. It was built about 1755, and is of hewn-log construction. It consists of three rooms, with the westernmost room having two of its three exterior walls of stone construction. It sits on a rubble limestone foundation.The house served as George Washington's headquarters while he was supervising the construction of Fort Loudoun from the fall of 1755 until he moved into the fort in December 1756.It was added to the National Register of Historic Places in 1976. It is located in the Winchester Historic District.