The George Washington Hotel (Winchester, Virginia)

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.

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.

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.

Mount Hebron Cemetery and Gatehouse is a historic cemetery and gatehouse located at Winchester, Virginia. The cemetery was established in 1844 on two older churchyards, including that of Christ Episcopal Church in 1853. Many Civil War soldiers who died in Winchester's hospitals were interred in this cemetery, but after the war, the Union Burial Corps reinterred many Union dead into the Winchester National Cemetery established nearby, or to their home towns. The 1866 expansion included Stonewall Confederate Cemetery for 2,576 Confederate war dead. Iron fence added in 1891 and the Chateauesque style limestone gatehouse for superintendent added in 1902.Founding Father Daniel Roberdeau (1727–1795) and Revolutionary War hero Daniel Morgan (1736–1802) are buried at Mount Hebron. It was added to the National Register of Historic Places in 2009.

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.

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 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.

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 Stonewall Jackson's Headquarters Museum is a historic house located at 415 North Braddock Street in the Historic District of Winchester, Virginia.

Christ Church, or Christ Episcopal Church, is an Anglican church in Winchester, Frederick County, Virginia. The church was founded in 1738, with its first vestry elected in 1742. It is the seat of Frederick Parish, Diocese of Virginia, which once covered half of the Shenandoah valley and western Virginia, including what became West Virginia. The current church building, the parish's third, was designed by Robert Mills (who also designed the Washington Monument and Monumental Church in Richmond, Virginia) - it was completed in 1828, and is the oldest church building continuously used for religious purposes in the county. It is a contributing building in the local Historic District which predates the National Register of Historic Places, and which has been expanded three times since 1980.The early organizational history of Christ Church differs significantly from that of the Episcopal Church in Frederick, Maryland, the nearby and similar gateway parish during colonial era settlement in Maryland, although the two churches had similar experiences of expansion and during the American Civil War, and remain prominent both architecturally and socially in their historic towns. Christ Church is now one of five Anglican churches in the historic Virginia gateway city. The other churches are: historic St. Paul African Methodist Episcopal (founded in 1867, one of the first AME churches and also a contributing building to the historic district), St. Paul's on the Hill (which began as a mission of this church at the city's outskirts in 1966 and became an independent parish in 1996), St. Michael Anglican Church (founded by a British movement and using the 1928 Book of Common Prayer) and Winchester Anglican Church (founded as a mission of the Anglican Church in North America circa 2010) .

Fair Mount is a historic home located at Winchester, Virginia. It was built about 1809 by Lewis Barnett for local merchant Joseph Tidball. It is a two-story, five bay, stuccoed stone dwelling, with 1+1⁄2-story flanking wings. The house exhibits elements of the Late Georgian style in its massing and elements of the Federal style in its detailing. It was remodeled in 1929 in the Colonial Revival Style and the formal gardens and garage constructed.It was added to the National Register of Historic Places in 2004. It is located in the Winchester Historic District.

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.