Winchester, VA

Winchester held the ninety-ninth Shenandoah Apple Blossom Festival from April 24 through May 3, 2026, extending a tradition begun in 1924. The calendar now spans parades, fireworks, dances, a wine festival, road races, luncheons, and a carnival; the carnival also set aside periods without music or flashing ride lights. Jim Barnett Park handles many of the city's other large gatherings and everyday recreation. Its more than 170 acres contain athletic fields, two pools, a recreation center, playgrounds, a lake, and picnic areas. Handley Library adds a year-round civic venue in a 1913 domed building downtown, opening six days a week and four evenings for archives research, children's programs, game nights, technology help, tours, and community gatherings. Winchester had 28,120 residents in 2020 and an estimated 28,272 in July 2025.

During 2020 through 2024, owner occupancy was 44 percent, the median owner-occupied value was $343,000, median monthly owner costs with a mortgage were $1,782, and median gross rent was $1,315. For that 2020 through 2024 period, median household income was $63,974, poverty was 22 percent, workers averaged about 20 minutes of travel to work, and one in five people age five or older spoke a language other than English at home. Winchester Transit operates two fixed loops and an on-demand service six days a week; loop buses arrive every half hour and stop at Old Town, the medical center, and the Museum of the Shenandoah Valley. At the museum, galleries and formal gardens are joined by trails that open daily from morning to dusk.