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Shenandoah University is a private university in Winchester, Virginia. It has an enrollment of approximately 4,000 students across more than 200 areas of study in six schools: College of Arts & Sciences (including the Division of Education and Leadership and the Division of Applied Technology), School of Business, Shenandoah Conservatory, Bernard J. Dunn School of Pharmacy, Eleanor Wade Custer School of Nursing, and the School of Health Professions (Athletic Training, Occupational Therapy, Physician Assistant Studies and Physical Therapy). Shenandoah University is one of five United Methodist Church-affiliated institutions of higher education in the Commonwealth of Virginia.

Abram's Delight is a historic home located in Winchester, Virginia. Built in 1754, it is the oldest house in the city. It was owned by the Hollingsworth family for almost 200 years and is typical of the Shenandoah Valley architecture of the Scotch-Irish settlers. The property was added to the Virginia Landmarks Register (VLR) in 1972 and the National Register of Historic Places (NRHP) in 1973. Abram's Delight currently serves as a historic house museum.

Shentel Stadium is a 3,000-seat stadium in Winchester, Virginia where it serves as home to the football team of Shenandoah University. Built in 2001 the stadium's name comes from a sponsorship agreement with Shenandoah Telecommunications Company (or Shentel). It is home to the 2004, 2005 USA South Conference Football Champions. It is also home to the men's and women's soccer teams along with the men's and women's lacrosse teams. The stadium's field is an artificial playing surface.

Winchester Coca-Cola Bottling Works is a historic Coca-Cola bottling plant located at Winchester, Virginia. It was built in 1940–1941, and is a two-story, reinforced concrete Art Deco style factory faced with brick. The asymmetrical four-bay façade features large plate-glass shop windows on the first floor that allowed the bottling operation to be viewed by the passing public. It has a one-story rear addition built in 1960, and a two-story warehouse added in 1974. Also on the property is a contributing one-story, brick storage building with a garage facility constructed in 1941. The facility closed in 2006.It was added to the National Register of Historic Places in 2008.

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 Triangle Diner is an American diner in Winchester, Virginia. It was built in 1948 by the Jerry O'Mahony Diner Company of Elizabeth, New Jersey.It is one of the best preserved classic diners in America, with close to 100% of the original features still intact. Key features include elaborate stainless steel ornamentation on the exterior, rounded interior ceiling with hidden lighting cove on all sides, a counter with stools and booths for patron seating, and terrazzo concrete floor. O'Mahony was a significant and prolific diner manufacturing company and set high standards for diner construction quality and craftsmanship. O'Mahony's work served as an inspiration for other diner manufacturers throughout the 1940s and 1950s. The Triangle Diner is an example of "Moderne architectural features" that are representative of the stainless steel prefabricated diners of the post–World War II era. The entire diner building – approximately 43 by 16 feet – was built at the O'Mahony Diner Company factory in New Jersey and once fully complete was then transported by train nearly 300 miles to Winchester, Virginia. It has been at the same intersection in Winchester since it first arrived, more than 60 years ago. Diners of this design somewhat resemble and are often confused with railroad cars removed from their wheels.The Triangle Diner was listed on the National Register of Historic Places by the U.S. Department of the Interior on March 31, 2010, and was added to the Virginia Landmarks Register on December 17, 2009. The building is currently closed pending the completion of a comprehensive restoration that stalled out in 2014. The Triangle Diner is the older of only two stainless steel O’Mahony diners in Virginia. Of the more than 2,000 O'Mahony diners once built, only a few dozen still remain nationwide. Country music legend Patsy Cline worked at the diner for three years after dropping out of high school to help support her mother and siblings.

The First Battle of Winchester, fought on May 25, 1862, in and around Frederick County, Virginia, and Winchester, Virginia, was a major victory in Confederate Army Maj. Gen. Thomas J. "Stonewall" Jackson's Campaign through the Shenandoah Valley during the American Civil War. Jackson enveloped the right flank of the Union Army under Maj. Gen. Nathaniel P. Banks and pursued it as it fled across the Potomac River into Maryland. Jackson's success in achieving force concentration early in the fighting allowed him to secure a more decisive victory which had escaped him in previous battles of the campaign.

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."

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.

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.

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.

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.