Hawthorne and Old Town Spring

Hexagon House is a historic home in Winchester, Virginia built between 1871 and 1873 and is a two-story, hexagon floor-plan, brick dwelling, with semi-hexagonal ground-floor projections and an ornate three-bay veranda-style porch on the principal façade. It has a central chimney and is topped by dark red, low-pitched roofs extending to substantial white cornicing.Completed in 1873 by architect Brice Leatherman for James W. Burgess in a style designed to open up interior space and let in more natural light. Even rarer than octagon houses built on similar principles.It was added to the National Register of Historic Places in 1987.

Glen Burnie is a historic home located at Winchester, Virginia. It consists of a 2+1⁄2-story central section built in two sections about 1794, with flanking two-bay, two-story wings built in 1959. It is a brick dwelling in the Georgian style.Built in 1794 by Robert Wood, son of James and Mary Wood. James founded Frederick Town (later Winchester) in 1744.It was added to the National Register of Historic Places in 1979.The house is now part of the Museum of the Shenandoah Valley.

Daniel Morgan House, also known as the George Flowerdew Norton House, Boyd House, and Sherrard House, is a historic home located at Winchester, Virginia. It is a 2+1⁄2-story, seven bay, 17 room, Late Georgian style brick dwelling. It has a side-gable roof and paired double interior chimneys. The oldest section was built about 1786 for George Flowerdew Norton, and the western stuccoed brick wing was built for Daniel Morgan (1736–1802) about 1800. A brick kitchen, built about 1820 is attached to the north side of the dwelling and two-story addition, constructed about 1885, is attached to the northwest corner of the house. A one-room addition was added to the eastern side about 1890, and a second-story room was built above the back porch about 1915. Also on the property is a contributing coursed stone retaining wall (c. 1900).It was added to the National Register of Historic Places in 2013. It is located in the Winchester Historic District. Gen.Daniel Morgan died in this house on July 6, 1802. The house then was the home of his daughter.

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.

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) .

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 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.

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

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.

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.

John Handley High School (usually referred to as Jhhs) is an endowed public high school located in the city of Winchester, Virginia. It is a part of Winchester Public Schools. It was founded by a grant from Judge John Handley, hence the school mascot, the Judges. Construction on John Handley High School started in 1922, and continues to the present day. Recently, the school completed the final phase of its multimillion-dollar renovation with the addition of an 8-lane track and a turf football field. The school is planning renovations to its tennis courts in the upcoming years, due in part to the girls' three-peat state champions. In 1998, Handley was placed on the list of the National Register of Historic Places "for its local historic significance as well as its prominence as an architectural landmark."

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.