The Shenandoah Apple Blossom Festival returns to Winchester from 24 April to 3 May 2026, celebrating its 99th year. Enjoy 10 days and 50+ events including parades, live entertainment, a carnival, wine festival, races, concerts and family-friendly activities. Spanning the Northern Shenandoah Valley, this iconic festival draws over 250,000 visitors each year. Book early and make a week of it.