Shentel Stadium

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.

The Apple Blossom Mall is a 473,672 square feet (44,006 m2) shopping mall that was built in 1982 on the south side of Winchester, Virginia. It has 83 stores. Its anchor stores are Belk (former Leggett), AMC Classic, and JCPenney. The mall's one vacant anchor space was once occupied by Sears. The shopping mall was acquired by Simon Property Group in 1999. It is now managed and 49.1% owned by Simon Property Group. In 2007, Simon Property Group announced a major lifestyle redevelopment at Apple Blossom Mall, including the addition of a RC Theatres 16-screen complex on the property. Construction on the theatres was to begin in the spring of 2007 with the opening scheduled for late 2007 or early 2008. This lifestyle center which was to include three lifestyle-type tenants, two big boxes, an additional department store and new restaurants never materialized. There is now an AMC Classic (formerly Carmike) located in the mall. In mid-2012, mall representatives announced renovation plans for the mall. Among them will be new floors and lighting, a children's play area, and a 12-screen theater to replace the existing theater.On November 7, 2019, it was announced that Sears would be closing this location a part of a plan to close 96 stores nationwide. The store closed in February 2020.On March 29, 2020, the mall closed temporarily due to COVID-19 concerns. It reopened on May 15, 2020.

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.

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.

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.

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.

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.

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.

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.