The Shenandoah Apple Blossom Festival has been held in Winchester every spring since 1924, timed to coincide with the blooming of the apple orchards that ring the city. The festival runs for several days in late April and early May and draws roughly a quarter million visitors — an enormous number for a city of 28,000. The centerpiece is the Grand Feature Parade, which runs through the downtown streets and is billed as the world's largest firemen's parade, featuring fire companies from across the eastern United States and Canada.
Beyond the parade, the festival includes a carnival, a 10K road race, concerts across multiple stages, and the coronation of a Queen Shenandoah, a tradition that has attracted celebrity queens ranging from local dignitaries to actresses and television personalities over the years. If you're timing a visit to Winchester for the spring, it's worth knowing that hotel rooms within 30 miles fill months in advance. But the festival captures something genuine about this corner of Virginia — the orchards are real, the civic pride is real, and the spectacle is considerably more entertaining than it sounds on paper.