Stonewall Jackson's Headquarters Museum

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.

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.

Beth El Congregation is a Reform Judaism congregation located at 520 Fairmont Avenue in Winchester, Virginia, in the United States. The local Jewish community didn't develop until the late-19th century. They were mostly merchants and observed dietary laws, often having to travel to Baltimore for supplies. In 1908, the Jewish citizens decided to observe its first High Holy Days. Two local leaders learned shochet laws, enabling local Jews to keep kosher without having to travel out of town. By the 1930s, there were over 50 Jews living in Winchester and another two dozen in nearby towns. During that decade, Beth El was formally established and the congregation met on the third floor of the Odd Fellows Building. The local Jewish Women's Club and B'nai B'rith Lodge were also established during that decade. Services were led by congregants until after World War II. By that time, many in the congregation no longer observed Orthodox practices, and Reform Judaism began to take hold. Rabbis studying at Hebrew Union College would come each year to conduct services during High Holy Days. In 1954, a synagogue was built, allowing Beth El to have a permanent place to gather and worship. A dedication ceremony was attended by dignitaries including Representative Burr Harrison and Senator Harry F. Byrd. The local non-Jewish community played a major role in raising funds for the new synagogue, with over $12,000 in donations given to the congregation. This type of interfaith practice would continue throughout Beth El's history. After the synagogue was built, there was a rotating number of rabbis leading services, but one cantor, Lloyd Robb, would remain for 40 years. It wasn't until 1991 when Beth El's first rabbi, Dan Isaac, was hired. A major renovation was undertaken beginning in 2013 to accommodate elderly and disabled attendees, move the sanctuary entrance to a new portion of the building, and to update the sanctuary and other rooms. Following the 2018 Pittsburgh synagogue shooting, security measures were installed at Beth El. The current rabbi is Aaron Stucker-Rozovsky, who also holds the rank of major in the National Guard. He arrived during the COVID-19 pandemic, when services were held online and congregants would deliver groceries to the elderly. Other charitable activities Beth El participates in include hosting an annual Migrant's Lunch, volunteering at the local hospital on Christmas so that non-Jews may have the day off, and providing assistance to the Winchester Area Temporary Transitional Shelter. Prominent past and current members include Winchester Mayor Charles Zuckerman and Ron Kaplan, former CEO of Trex Company, Inc.

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.

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.

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.

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.

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) .

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.

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.

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.

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.