2024 Major Events

The Main Street program of Old Town Winchester is happy to present the 2024 year-at-a-glance calendar for special events and offerings taking place in Old Town this year. See below for a full list of all currently scheduled major events and their respective sponsoring organizations, and stay tuned for more details throughout the year on additional events and details!


  • FEBRUARY 3-28: Black History Month Art Walk [Old Town Winchester & Arte Libre VA]
  • SAT FEBRUARY 10: Chocolate Escape [Old Town Winchester]
  • FEBRUARY 19-25: Restaurant Week [Winchester Main Street Foundation]
  • SAT MARCH 16: Celtic Fest [Old Town Winchester]
  • FRI APRIL 5: First Friday [Old Town Winchester]
  • APRIL 26-27: Apple Blossom Bloomin’ Wine Fest [Shenandoah Apple Blossom Festival]
  • FRI MAY 3: Apple Blossom Firefighters’ Parade [Shenandoah Apple Blossom Festival]
  • SAT MAY 4: Apple Blossom Grand Feature Parade [Shenandoah Apple Blossom Festival]
  • SAT JUNE 1: Hop Blossom Beer Festival [Hop Blossom]
  • FRI JUNE 7: First Friday [Old Town Winchester]
  • SAT JUNE 8 : KidzFest [Old Town Winchester]
  • FRI JUNE 14: Juneteenth Celebration [Old Town Winchester & Hood-Love]
  • WED JULY 3: Rockin’ Independence Eve [Old Town Winchester]
  • FRI JULY 5: First Friday [Old Town Winchester]
  • FRI AUGUST 2: First Friday [Old Town Winchester]
  • FRI SEPTEMBER 6: First Friday [Old Town Winchester]
  • SEPTEMBER 7-8: ShenArts Fest [Shenandoah Arts Council]
  • SAT SEPTEMBER 14: Fiddles & Fifths [Winchester EDA]
  • SAT SEPTEMBER 21: Celebración of Winchester [Winchester Main Street Foundation]
  • FRI OCTOBER 4: First Friday [Old Town Winchester]
  • SAT OCTOBER 26: HalloWinchester [Old Town Winchester]
  • FRI NOVEMBER 1: Día de los Muertos [Old Town Winchester, Shenandoah University & Arte Libre VA]
  • NOVEMBER 29- DECEMBER 1: Windependent Weekend [Old Town Winchester]
  • DECEMBER 6-8: Old Town Winter Village
  • TUE DECEMBER 31: NYE Apple Drop
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