Douglas School

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.

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.

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.

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.

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

Built by Confederate Lieutenant Collier and Virginia militia with the aid of Federal prisoners, the Fort Collier redoubt guarded the north entrance of Winchester, Virginia on the east side of the Martinsburg Pike. During later Federal occupations, it was known as Battery No. 10. The fort was set on low ground, and generally offered little military advantage, except as a guard post for the pike. LtGen Jubal Early used it as part of his defensive works in the Third Battle of Winchester.

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.

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.

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.

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.